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Showing metabocard for Citrulline (HMDB0000904)

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enzymes (14) Show 14 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:54 UTC
HMDB IDHMDB0000904
Secondary Accession Numbers
  • HMDB00904
Metabolite Identification
Common NameCitrulline
DescriptionCitrulline, also known as Cit or δ-ureidonorvaline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Citrulline has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. Citrulline exists in all living species, ranging from bacteria to humans. Within humans, citrulline participates in a number of enzymatic reactions. In particular, citrulline can be biosynthesized from carbamoyl phosphate and ornithine which is catalyzed by the enzyme ornithine carbamoyltransferase. In addition, citrulline and L-aspartic acid can be converted into argininosuccinic acid through the action of the enzyme argininosuccinate synthase. In humans, citrulline is involved in the metabolic disorder called argininemia. Citrulline has also been found to be associated with several diseases such as ulcerative colitis, rheumatoid arthritis, and citrullinemia type II. Citrulline has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and fumarase deficiency. Outside of the human body, citrulline is found, on average, in the highest concentration in a few different foods such as wheats, oats, and cucumbers and in a lower concentration in swiss chards, yellow wax beans, and potato. Citrulline has also been detected, but not quantified in several different foods, such as epazotes, lotus, common buckwheats, strawberry guava, and italian sweet red peppers. Citrulline is a potentially toxic compound. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. It is also produced from arginine as a byproduct of the reaction catalyzed by NOS family (NOS; EC1.14.13.39).
Structure
Data?1676999717
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000904 (Citrulline)


  Mrv1652309042000132D          

 12 11  0  0  1  0            999 V2000
   -0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  1  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000904 (Citrulline)

HMDB0000904
     RDKit          3D
Citrulline
 25 24  0  0  0  0  0  0  0  0999 V2000
    4.8263   -0.4259   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389    0.3608   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957    1.6080   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637   -0.2349   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    0.6324    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -0.1235    0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.8507    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443    0.1831    0.5635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6210   -0.5802    1.7729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519   -0.6314   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048   -1.8307   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.1084   -1.9053 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6758   -0.1179   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.3747    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.2712    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    1.4012    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    1.1809   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -0.7281   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -0.8324    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796    1.4671   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0539    1.5333    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    0.9978    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   -1.4955    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -0.6770    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    0.2165   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  1
  9 23  1  0
  9 24  1  0
 12 25  1  0
M  END
Download

3D SDF for HMDB0000904 (Citrulline)


  Mrv1652309042000132D          

 12 11  0  0  1  0            999 V2000
   -0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.1833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5 12  1  1  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  1  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000904

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CCCNC(N)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1

> <INCHI_KEY>
RHGKLRLOHDJJDR-BYPYZUCNSA-N

> <FORMULA>
C6H13N3O3

> <MOLECULAR_WEIGHT>
175.1857

> <EXACT_MASS>
175.095691297

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.34757818367823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-(carbamoylamino)pentanoic acid

> <ALOGPS_LOGP>
-3.27

> <JCHEM_LOGP>
-3.9319578381140263

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.333969157335531

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2682474980163243

> <JCHEM_PKA_STRONGEST_BASIC>
9.225134668659093

> <JCHEM_POLAR_SURFACE_AREA>
118.43999999999998

> <JCHEM_REFRACTIVITY>
41.329

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-citrulline

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000904 (Citrulline)

HMDB0000904
     RDKit          3D
Citrulline
 25 24  0  0  0  0  0  0  0  0999 V2000
    4.8263   -0.4259   -0.2908 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389    0.3608   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7957    1.6080   -0.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637   -0.2349   -0.0045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    0.6324    0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -0.1235    0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    0.8507    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5443    0.1831    0.5635 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6210   -0.5802    1.7729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519   -0.6314   -0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3048   -1.8307   -0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -0.1084   -1.9053 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6758   -0.1179   -0.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8701   -1.3747    0.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.2712    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    1.4012    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    1.1809   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311   -0.7281   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0376   -0.8324    1.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796    1.4671   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0539    1.5333    1.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046    0.9978    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1361   -1.4955    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -0.6770    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8576    0.2165   -2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  1
  9 23  1  0
  9 24  1  0
 12 25  1  0
M  END
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PDB for HMDB0000904 (Citrulline)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.428   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.667  -0.342   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -4.001   0.428   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.428   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.342   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -5.335  -0.342   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.334   0.428   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.342   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -0.342   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.001   1.968   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   1.968   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.667  -1.882   0.000  0.00  0.00           N+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2   10    6                                                  
CONECT    4   11    5    9                                                  
CONECT    5    4   12    7                                                  
CONECT    6    3                                                            
CONECT    7    5    8                                                       
CONECT    8    1    7                                                       
CONECT    9    4                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0000904 (Citrulline)

COMPND    HMDB0000904
HETATM    1  N1  UNL     1       4.826  -0.426  -0.291  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.639   0.361  -0.201  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.796   1.608  -0.307  1.00  0.00           O  
HETATM    4  N2  UNL     1       2.364  -0.235  -0.005  1.00  0.00           N  
HETATM    5  C2  UNL     1       1.222   0.632   0.074  1.00  0.00           C  
HETATM    6  C3  UNL     1      -0.068  -0.123   0.284  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.218   0.851   0.356  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.544   0.183   0.564  1.00  0.00           C  
HETATM    9  N3  UNL     1      -2.621  -0.580   1.773  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.952  -0.631  -0.621  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.305  -1.831  -0.486  1.00  0.00           O  
HETATM   12  O3  UNL     1      -2.959  -0.108  -1.905  1.00  0.00           O  
HETATM   13  H1  UNL     1       5.676  -0.118  -0.793  1.00  0.00           H  
HETATM   14  H2  UNL     1       4.870  -1.375   0.169  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.318  -1.271   0.073  1.00  0.00           H  
HETATM   16  H4  UNL     1       1.355   1.401   0.862  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.137   1.181  -0.891  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.231  -0.728  -0.656  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.038  -0.832   1.104  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.280   1.467  -0.541  1.00  0.00           H  
HETATM   21  H9  UNL     1      -1.054   1.533   1.215  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.305   0.998   0.640  1.00  0.00           H  
HETATM   23  H11 UNL     1      -2.136  -1.496   1.724  1.00  0.00           H  
HETATM   24  H12 UNL     1      -3.635  -0.677   2.025  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.858   0.216  -2.270  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   10   22
CONECT    9   23   24
CONECT   10   11   11   12
CONECT   12   25
END
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SMILES for HMDB0000904 (Citrulline)

N[C@@H](CCCNC(N)=O)C(O)=O
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INCHI for HMDB0000904 (Citrulline)

InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-2-Amino-5-ureidopentanoic acidChEBI
2-Amino-5-ureidovaleric acidChEBI
alpha-Amino-delta-ureidovaleric acidChEBI
CitChEBI
delta-UreidonorvalineChEBI
L-2-Amino-5-ureidovaleric acidChEBI
N(5)-(Aminocarbonyl)-L-ornithineChEBI
N5-(Aminocarbonyl)ornithineChEBI
N5-CarbamoylornithineChEBI
N(delta)-CarbamylornithineChEBI
(S)-2-Amino-5-ureidopentanoateGenerator
2-Amino-5-ureidovalerateGenerator
a-Amino-delta-ureidovalerateGenerator
a-Amino-delta-ureidovaleric acidGenerator
alpha-Amino-delta-ureidovalerateGenerator
Α-amino-δ-ureidovalerateGenerator
Α-amino-δ-ureidovaleric acidGenerator
Δ-ureidonorvalineGenerator
L-2-Amino-5-ureidovalerateGenerator
N(Δ)-carbamylornithineGenerator
a-Amino-δ-ureidovalerateHMDB
a-Amino-δ-ureidovaleric acidHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoateHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoic acidHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoateHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoic acidHMDB
2-Amino-5-uredovalerateHMDB
2-Amino-5-uredovaleric acidHMDB
a-Amino-D-ureidovalerateHMDB
a-Amino-D-ureidovaleric acidHMDB
alpha-Amino-gamma-ureidovalerateHMDB
alpha-Amino-gamma-ureidovaleric acidHMDB
Amino-ureidovalerateHMDB
Amino-ureidovaleric acidHMDB
CIRHMDB
CytrullineHMDB
D-UreidonorvalineHMDB
DL-CitrullineHMDB
GammaureidonorvalineHMDB
H-Cit-OHHMDB
L(+)-2-Amino-5-ureidovalerateHMDB
L(+)-2-Amino-5-ureidovaleric acidHMDB
L(+)-CitrullineHMDB
L-2-Amino-5-ureido-valerateHMDB
L-2-Amino-5-ureido-valeric acidHMDB
L-CitrullineHMDB
L-CytrullineHMDB
L-N5-Carbamoyl-ornithineHMDB
N()-CarbamylornithineHMDB
N(5)-(Aminocarbonyl)-DL-ornithineHMDB
N-CarbamylornithineHMDB
N5-(Aminocarbonyl)-L-ornithineHMDB
N5-(Aminocarbonyl)-ornithineHMDB
N5-Carbamoyl-L-ornithineHMDB
N5-CarbamylornithineHMDB
ND-CarbamylornithineHMDB
Ndelta-carbamy-ornithineHMDB
Ndelta-carbamylornithineHMDB
Ngamma-carbamylornithineHMDB
SitrullineHMDB
UreidonorvalineHMDB
UreidovalerateHMDB
Ureidovaleric acidHMDB
Chemical FormulaC6H13N3O3
Average Molecular Weight175.1857
Monoisotopic Molecular Weight175.095691297
IUPAC Name(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Traditional NameL-citrulline
CAS Registry Number372-75-8
SMILES
N[C@@H](CCCNC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
InChI KeyRHGKLRLOHDJJDR-BYPYZUCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Isourea
  • Amino acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point235.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility212 mg/mLNot Available
LogP-3.19SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg133.330932474
[M-H]-Not Available135.6http://allccs.zhulab.cn/database/detail?ID=AllCCS00000508
[M+H]+Not Available138.011http://allccs.zhulab.cn/database/detail?ID=AllCCS00000508
Predicted Molecular Properties
PropertyValueSource
Water Solubility21.8 g/LALOGPS
logP-3.3ALOGPS
logP-3.9ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)2.27ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability17.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.39131661259
DarkChem[M-H]-135.23731661259
AllCCS[M+H]+139.35732859911
AllCCS[M-H]-136.16832859911
DeepCCS[M+H]+134.78630932474
DeepCCS[M-H]-130.95830932474
DeepCCS[M-2H]-168.53630932474
DeepCCS[M+Na]+144.07430932474
AllCCS[M+H]+139.432859911
AllCCS[M+H-H2O]+135.632859911
AllCCS[M+NH4]+142.932859911
AllCCS[M+Na]+143.932859911
AllCCS[M-H]-136.232859911
AllCCS[M+Na-2H]-137.732859911
AllCCS[M+HCOO]-139.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitrullineN[C@@H](CCCNC(N)=O)C(O)=O2589.7Standard polar33892256
CitrullineN[C@@H](CCCNC(N)=O)C(O)=O1683.7Standard non polar33892256
CitrullineN[C@@H](CCCNC(N)=O)C(O)=O2259.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citrulline,1TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(N)=O1921.7Semi standard non polar33892256
Citrulline,1TMS,isomer #2C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O1986.3Semi standard non polar33892256
Citrulline,1TMS,isomer #3C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O2028.9Semi standard non polar33892256
Citrulline,1TMS,isomer #4C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(N)=O1980.4Semi standard non polar33892256
Citrulline,2TMS,isomer #1C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C2008.7Semi standard non polar33892256
Citrulline,2TMS,isomer #1C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C1838.7Standard non polar33892256
Citrulline,2TMS,isomer #1C[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C3301.8Standard polar33892256
Citrulline,2TMS,isomer #2C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C2009.6Semi standard non polar33892256
Citrulline,2TMS,isomer #2C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C1827.2Standard non polar33892256
Citrulline,2TMS,isomer #2C[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C3171.1Standard polar33892256
Citrulline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C1900.2Semi standard non polar33892256
Citrulline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C1910.3Standard non polar33892256
Citrulline,2TMS,isomer #3C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C3399.1Standard polar33892256
Citrulline,2TMS,isomer #4C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O2087.1Semi standard non polar33892256
Citrulline,2TMS,isomer #4C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O1797.8Standard non polar33892256
Citrulline,2TMS,isomer #4C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O3129.9Standard polar33892256
Citrulline,2TMS,isomer #5C[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C2152.2Semi standard non polar33892256
Citrulline,2TMS,isomer #5C[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C1902.3Standard non polar33892256
Citrulline,2TMS,isomer #5C[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C3502.1Standard polar33892256
Citrulline,2TMS,isomer #6C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O2046.2Semi standard non polar33892256
Citrulline,2TMS,isomer #6C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O1919.6Standard non polar33892256
Citrulline,2TMS,isomer #6C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O3163.7Standard polar33892256
Citrulline,2TMS,isomer #7C[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C2093.7Semi standard non polar33892256
Citrulline,2TMS,isomer #7C[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C1891.3Standard non polar33892256
Citrulline,2TMS,isomer #7C[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C3452.1Standard polar33892256
Citrulline,2TMS,isomer #8C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C2050.1Semi standard non polar33892256
Citrulline,2TMS,isomer #8C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C1895.5Standard non polar33892256
Citrulline,2TMS,isomer #8C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C3333.9Standard polar33892256
Citrulline,3TMS,isomer #1C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2096.3Semi standard non polar33892256
Citrulline,3TMS,isomer #1C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1851.2Standard non polar33892256
Citrulline,3TMS,isomer #1C[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C2690.2Standard polar33892256
Citrulline,3TMS,isomer #10C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C2089.8Semi standard non polar33892256
Citrulline,3TMS,isomer #10C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C2058.5Standard non polar33892256
Citrulline,3TMS,isomer #10C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C)[Si](C)(C)C3004.5Standard polar33892256
Citrulline,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C2151.4Semi standard non polar33892256
Citrulline,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C1948.9Standard non polar33892256
Citrulline,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C)[Si](C)(C)C3137.4Standard polar33892256
Citrulline,3TMS,isomer #3C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C1958.1Semi standard non polar33892256
Citrulline,3TMS,isomer #3C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C1929.2Standard non polar33892256
Citrulline,3TMS,isomer #3C[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C2912.8Standard polar33892256
Citrulline,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C2019.0Semi standard non polar33892256
Citrulline,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C1976.5Standard non polar33892256
Citrulline,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C2886.8Standard polar33892256
Citrulline,3TMS,isomer #5C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C1982.3Semi standard non polar33892256
Citrulline,3TMS,isomer #5C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C1945.7Standard non polar33892256
Citrulline,3TMS,isomer #5C[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C2843.1Standard polar33892256
Citrulline,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2134.6Semi standard non polar33892256
Citrulline,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O1953.6Standard non polar33892256
Citrulline,3TMS,isomer #6C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O2726.6Standard polar33892256
Citrulline,3TMS,isomer #7C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2084.8Semi standard non polar33892256
Citrulline,3TMS,isomer #7C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C1950.8Standard non polar33892256
Citrulline,3TMS,isomer #7C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C2710.0Standard polar33892256
Citrulline,3TMS,isomer #8C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2247.6Semi standard non polar33892256
Citrulline,3TMS,isomer #8C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1899.6Standard non polar33892256
Citrulline,3TMS,isomer #8C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2812.7Standard polar33892256
Citrulline,3TMS,isomer #9C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O2148.0Semi standard non polar33892256
Citrulline,3TMS,isomer #9C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O2018.9Standard non polar33892256
Citrulline,3TMS,isomer #9C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(N)=O3011.0Standard polar33892256
Citrulline,4TMS,isomer #1C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2076.4Semi standard non polar33892256
Citrulline,4TMS,isomer #1C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2011.6Standard non polar33892256
Citrulline,4TMS,isomer #1C[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2401.4Standard polar33892256
Citrulline,4TMS,isomer #2C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2047.3Semi standard non polar33892256
Citrulline,4TMS,isomer #2C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C1963.9Standard non polar33892256
Citrulline,4TMS,isomer #2C[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C2366.3Standard polar33892256
Citrulline,4TMS,isomer #3C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2233.8Semi standard non polar33892256
Citrulline,4TMS,isomer #3C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1946.5Standard non polar33892256
Citrulline,4TMS,isomer #3C[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2511.2Standard polar33892256
Citrulline,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2124.9Semi standard non polar33892256
Citrulline,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2029.8Standard non polar33892256
Citrulline,4TMS,isomer #4C[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2843.2Standard polar33892256
Citrulline,4TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2052.2Semi standard non polar33892256
Citrulline,4TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2115.2Standard non polar33892256
Citrulline,4TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2590.7Standard polar33892256
Citrulline,4TMS,isomer #6C[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2255.5Semi standard non polar33892256
Citrulline,4TMS,isomer #6C[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2064.8Standard non polar33892256
Citrulline,4TMS,isomer #6C[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2519.2Standard polar33892256
Citrulline,4TMS,isomer #7C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O2144.6Semi standard non polar33892256
Citrulline,4TMS,isomer #7C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O2125.3Standard non polar33892256
Citrulline,4TMS,isomer #7C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O2398.3Standard polar33892256
Citrulline,4TMS,isomer #8C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2213.7Semi standard non polar33892256
Citrulline,4TMS,isomer #8C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2050.9Standard non polar33892256
Citrulline,4TMS,isomer #8C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2498.2Standard polar33892256
Citrulline,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2289.4Semi standard non polar33892256
Citrulline,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2100.8Standard non polar33892256
Citrulline,5TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2278.5Standard polar33892256
Citrulline,5TMS,isomer #2C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2107.9Semi standard non polar33892256
Citrulline,5TMS,isomer #2C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2155.1Standard non polar33892256
Citrulline,5TMS,isomer #2C[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C2125.6Standard polar33892256
Citrulline,5TMS,isomer #3C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2245.5Semi standard non polar33892256
Citrulline,5TMS,isomer #3C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2071.0Standard non polar33892256
Citrulline,5TMS,isomer #3C[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2263.8Standard polar33892256
Citrulline,5TMS,isomer #4C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C2300.2Semi standard non polar33892256
Citrulline,5TMS,isomer #4C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C2247.3Standard non polar33892256
Citrulline,5TMS,isomer #4C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)N([Si](C)(C)C)[Si](C)(C)C2251.3Standard polar33892256
Citrulline,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2366.8Semi standard non polar33892256
Citrulline,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2254.6Standard non polar33892256
Citrulline,6TMS,isomer #1C[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2095.3Standard polar33892256
Citrulline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(N)=O2175.3Semi standard non polar33892256
Citrulline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O2250.5Semi standard non polar33892256
Citrulline,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O2270.9Semi standard non polar33892256
Citrulline,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(N)=O2194.3Semi standard non polar33892256
Citrulline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C2471.6Semi standard non polar33892256
Citrulline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C2259.9Standard non polar33892256
Citrulline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(N)=O)C(=O)O[Si](C)(C)C(C)(C)C3231.2Standard polar33892256
Citrulline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2480.5Semi standard non polar33892256
Citrulline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C2245.1Standard non polar33892256
Citrulline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C3077.7Standard polar33892256
Citrulline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C(C)(C)C2393.7Semi standard non polar33892256
Citrulline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C(C)(C)C2319.5Standard non polar33892256
Citrulline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(N)=O)[Si](C)(C)C(C)(C)C3391.2Standard polar33892256
Citrulline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2607.7Semi standard non polar33892256
Citrulline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2232.4Standard non polar33892256
Citrulline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O2962.9Standard polar33892256
Citrulline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C2594.9Semi standard non polar33892256
Citrulline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C2314.1Standard non polar33892256
Citrulline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N([C@@H](CCCNC(N)=O)C(=O)O)[Si](C)(C)C(C)(C)C3344.1Standard polar33892256
Citrulline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O2527.6Semi standard non polar33892256
Citrulline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O2350.6Standard non polar33892256
Citrulline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O3143.0Standard polar33892256
Citrulline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2533.6Semi standard non polar33892256
Citrulline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2329.1Standard non polar33892256
Citrulline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C3243.1Standard polar33892256
Citrulline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2527.3Semi standard non polar33892256
Citrulline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C2323.8Standard non polar33892256
Citrulline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C3192.6Standard polar33892256
Citrulline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2766.7Semi standard non polar33892256
Citrulline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2403.7Standard non polar33892256
Citrulline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2765.0Standard polar33892256
Citrulline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2747.4Semi standard non polar33892256
Citrulline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2625.2Standard non polar33892256
Citrulline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2982.3Standard polar33892256
Citrulline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2793.5Semi standard non polar33892256
Citrulline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2551.1Standard non polar33892256
Citrulline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(N)=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3110.6Standard polar33892256
Citrulline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2639.5Semi standard non polar33892256
Citrulline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2511.1Standard non polar33892256
Citrulline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3024.8Standard polar33892256
Citrulline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2698.5Semi standard non polar33892256
Citrulline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2572.1Standard non polar33892256
Citrulline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2914.6Standard polar33892256
Citrulline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2667.4Semi standard non polar33892256
Citrulline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2533.4Standard non polar33892256
Citrulline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2927.1Standard polar33892256
Citrulline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2827.0Semi standard non polar33892256
Citrulline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2545.0Standard non polar33892256
Citrulline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2799.2Standard polar33892256
Citrulline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2800.6Semi standard non polar33892256
Citrulline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2523.0Standard non polar33892256
Citrulline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C2816.4Standard polar33892256
Citrulline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2887.7Semi standard non polar33892256
Citrulline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2475.7Standard non polar33892256
Citrulline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2835.1Standard polar33892256
Citrulline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O2825.4Semi standard non polar33892256
Citrulline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O2575.2Standard non polar33892256
Citrulline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(N)=O3067.1Standard polar33892256
Citrulline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2951.6Semi standard non polar33892256
Citrulline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2723.2Standard non polar33892256
Citrulline,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2703.8Standard polar33892256
Citrulline,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2914.0Semi standard non polar33892256
Citrulline,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2671.9Standard non polar33892256
Citrulline,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2729.9Standard polar33892256
Citrulline,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3066.6Semi standard non polar33892256
Citrulline,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2659.6Standard non polar33892256
Citrulline,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2770.3Standard polar33892256
Citrulline,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3013.3Semi standard non polar33892256
Citrulline,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2751.3Standard non polar33892256
Citrulline,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(N)=O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3047.8Standard polar33892256
Citrulline,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2926.3Semi standard non polar33892256
Citrulline,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2818.4Standard non polar33892256
Citrulline,4TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2839.3Standard polar33892256
Citrulline,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3113.6Semi standard non polar33892256
Citrulline,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2787.7Standard non polar33892256
Citrulline,4TBDMS,isomer #6CC(C)(C)[Si](C)(C)N(C(=O)NCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2755.8Standard polar33892256
Citrulline,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O3022.9Semi standard non polar33892256
Citrulline,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2811.1Standard non polar33892256
Citrulline,4TBDMS,isomer #7CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2739.9Standard polar33892256
Citrulline,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3083.7Semi standard non polar33892256
Citrulline,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2748.3Standard non polar33892256
Citrulline,4TBDMS,isomer #8CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2790.6Standard polar33892256
Citrulline,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3311.2Semi standard non polar33892256
Citrulline,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2964.1Standard non polar33892256
Citrulline,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCNC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2696.3Standard polar33892256
Citrulline,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C3176.0Semi standard non polar33892256
Citrulline,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2976.1Standard non polar33892256
Citrulline,5TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2669.9Standard polar33892256
Citrulline,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3275.2Semi standard non polar33892256
Citrulline,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2931.0Standard non polar33892256
Citrulline,5TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2734.4Standard polar33892256
Citrulline,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3336.1Semi standard non polar33892256
Citrulline,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3045.3Standard non polar33892256
Citrulline,5TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2704.8Standard polar33892256
Citrulline,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3533.8Semi standard non polar33892256
Citrulline,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3230.7Standard non polar33892256
Citrulline,6TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCN(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2719.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Citrulline GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0920000000-2d92b63cd5d9648023b82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citrulline GC-MS (3 TMS)splash10-00di-9610000000-2e7cd23afc2adcef35a32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citrulline GC-EI-TOF (Non-derivatized)splash10-0a4i-0920000000-2d92b63cd5d9648023b82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Citrulline GC-MS (Non-derivatized)splash10-00di-9610000000-2e7cd23afc2adcef35a32017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-9100000000-1f8dd2c6648b104639c72016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9410000000-37909012a777213f85662017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrulline GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-0900000000-4c1d7af748a47e4899492012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-9000000000-988fced362fc0da157c92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00di-9000000000-0818e0e8bcee126924982012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-004j-0900000000-5fa8a338dcd2f2a6bdd22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-004i-0900000000-16763200aa07f7629ad42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-03di-3900000000-d9cfc5187aa799f6f9782012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0a4i-0900000000-10ee9a593e13550bec1c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-004i-0900000000-45d272576af34c9512a32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-014i-3900000000-6177a284fdea5a3f13062012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-0a4i-0900000000-d9456d45e2dbd7a3df102012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOFsplash10-004i-0900000000-ada57cdc73bda93be4832012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-008a-0904000000-23fbe48f82e515087d682012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-03di-5900000000-78afcbaf8b8b3eabf1742012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-001i-0900000000-8fb191d4c20fd54b92822012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative-QTOFsplash10-00di-0900000000-da484f0362a8dca5127e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-00e9-0900000000-46229b4f77feabb3f8572012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-001i-0900000000-4aca1022c393602a297d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-001i-0900000000-3bc2eff2e907b7734cc82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-001i-3900000000-2613bf40e3be814da86f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0006-9300000000-e83287bbc060eb9cf6f32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-056r-0900000000-694a8872bdfd7eec1f2b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-08fr-2900000000-15b4711991ea9985fb2b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00di-9300000000-915fbb73e0b728420e4a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00di-9000000000-67e60567f5c0627283502012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrulline LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-00di-9000000000-25140713431edd7c5eea2012-08-31HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Placenta
  • Platelet
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10-60 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified6-40 uMNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified6-60 uMInfant (1 - 3 months old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified8-70 uMChildren (3 months - 6 years old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified10-70 uMChildren (6 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
BloodDetected and Quantified19-51 uMInfant (0-1 year old)MaleNormal details
BloodDetected and Quantified38.0 (30.0-46.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified19-33 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified<43 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified8-47 uMNewborn (0-30 days old)Not SpecifiedNormal details
BloodDetected and Quantified10-45 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified10-50 uMChildren (1 - 13 years old)BothNormal details
BloodDetected and Quantified16 +/- 5 uMInfant (0-1 year old)BothNormal details
BloodDetected and Quantified29.8 +/- 7.91 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified35 +/- 10 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified31 +/- 8 uMChildren (1 - 13 years old)FemaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified20.4(16.7-26.3) uMChildren (1-13 uears old)Both
Normal		 details
BloodDetected and Quantified36.0 +/- 8.0 uMChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified37.0 +/- 9.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified35.0 +/- 10.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified37 +/- 9 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
 details
BloodDetected and Quantified38.0 (30.0-46.0) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified15.0-45.0 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified26 uMChildren (1-13 years old)Not SpecifiedNormal details
BloodDetected and Quantified5-37 uMNewborn (0-30 days old)Not SpecifiedNormal details
BloodDetected and Quantified10-60 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.8 +/- 1.0 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.8 +/- 1.8 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.62 (1.35-3.89) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.81+/- 1.23 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0-4.4 uMChildren (0 - 10 years old)Both
Normal
    • BC Children's Hos...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified0-4.5 uMAdolescent (>11 years old)Both
Normal
    • BC Children's Hos...
 details
Cerebrospinal Fluid (CSF)Detected and Quantified1.5 +/- 0.5 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified340 +/- 270 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified70 +/- 50 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified25.30 +/- 19.00 uMAdult (>18 years old)FemaleNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified8.1 +/- 0.94 uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified8.1 +/- 1.4 uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified26.2 +/- 33.1 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified9.2 +/- 2.1 uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified51.82 +/- 64.25 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified6.8 +/- 4.1 uMAdult (>18 years old)Male
Normal		 details
SalivaDetected and Quantified4.61 +/- 2.82 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal		 details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal		 details
UrineDetected and Quantified<1.018 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.08 (0.065-2.1) umol/mmol creatinineAdult (>18 years old)BothNormal
      Not Available
 details
UrineDetected and Quantified0.19 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.91 +/- 7.91 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified21.48 +/- 16.96 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified40.70 +/- 30.53 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified<1.58 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0.00-74.25 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
 details
UrineDetected and Quantified0-16.507 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified<1.36 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified<8.14 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.50 +/- 0.54 umol/mmol creatinineChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified1.1 +/- 0.84 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified0.99 +/- 0.69 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified1.81 (1.26-3.21) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
 details
UrineDetected and Quantified<6.45 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.24 +/- 0.23 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.8 (0.2-1.7) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified28.753 +/- 22.885 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified0 - 10.97 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 9.95 umol/mmol creatinineInfant (1 - 6 months old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 8.03 umol/mmol creatinineInfant (6 months - <1 year old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 7.01 umol/mmol creatinineChildren (1 - 2 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 5.99 umol/mmol creatinineChildren (2 - 4 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 4.97 umol/mmol creatinineChildren (4 - 13 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 3.96 umol/mmol creatinineAdolescent (13 - 21 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0 - 3.96 umol/mmol creatinineAdult (>21 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified1.4114 +/- 1.0599 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected and Quantified<1.58 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified0-10 umol/mmol creatinineInfant (0-1 year old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified15 uMChildren (1-13 years old)MalePearson Syndrome details
BloodDetected and Quantified2 uMInfant (0-1 year old)FemalePearson Syndrome details
BloodDetected and Quantified284 uMInfant (0-1 year old)MaleArgininosuccinic aciduria (ASL) details
BloodDetected and Quantified27.5 (10.0-45.0) uMAdult (>18 years old)BothArgininosuccinic aciduria
    • MetaGene: Metabol...
 details
BloodDetected and Quantified200.0 (100.0-300.0) uMChildren (1-13 years old)BothArgininosuccinic aciduria (ASL)
    • MetaGene: Metabol...
 details
BloodDetected and Quantified13.0 (6.0-20.0) uMAdult (>18 years old)BothPermanent intestinal failure details
BloodDetected and Quantified25.4 (23.4-27.4) uMAdult (>18 years old)BothAcute seizures details
BloodDetected and Quantified26.8 (25.4-28.2) uMAdult (>18 years old)Both
Epilepsy		 details
BloodDetected and Quantified26.9 (25.2-28.6) uMChildren (1-13 years old)Both
Epilepsy		 details
BloodDetected and Quantified13 uMNewborn (0-30 days old)Male
Narp Syndrome		 details
BloodDetected and Quantified3-5 uMChildren (1-13 years old)MaleNarp Syndrome details
BloodDetected and Quantified0-19 uMInfant (0-1 year old)BothNarp Syndrome details
BloodDetected and Quantified86-1542 uMAdult (>18 years old)BothCitrullinemia type II, adult-onset details
BloodDetected and Quantified6-21 uMChildren (1-13 years old)BothPhosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic details
BloodDetected and Quantified5 uMNewborn (0-30 days old)MalePhosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic details
BloodDetected and Quantified20.3(16.1-26.6) uMChildren (1-13 uears old)Both
Environmental enteric dysfunction		 details
BloodDetected and Quantified181 uMInfant (0-1 year old)MaleFumaric aciduria details
BloodDetected and Quantified0-7 uMNewborn (0-30 days old)MaleN-Acetylglutamate synthetase deficiency details
BloodDetected and Quantified13-23 uMInfant (0-1 year old)Male
N-Acetylglutamate synthetase deficiency		 details
BloodDetected and Quantified152-2752 uMChildren (1 - 13 years old)BothCitrullinemia Type I details
BloodDetected and Quantified94.97 +/- 11.18 uMElderly (>65 years old)BothAlzheimer's disease details
BloodDetected and Quantified28(0-275) uMChildren (1-13 years old)Female
Pearson Syndrome		 details
BloodDetected and Quantified286-485 uMNewborn (0-30 days old)BothCitrullinemia type II, neonatal-onset details
BloodDetected and Quantified6 +/- 5 uMChildren (1-13 years old)BothCutis laxa, autosomal recessive, type IIIA details
Cerebrospinal Fluid (CSF)Detected and Quantified27.0 +/- 2.6 uMAdult (>18 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified5.38 +/- 0.94 uMAdult (>18 years old)BothSchizophrenia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleGout details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Femalerheumatoid arthritis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPeriodontal diseases details
SalivaDetected and Quantified17.64 +/- 10.31 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified17.48 +/- 14.00 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleTooth Decay details
SalivaDetected and Quantified14.67 +/- 10.99 uMAdult (>18 years old)BothLewy body disease details
UrineDetected and Quantified63.800-549.400 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedFumaric aciduria details
UrineDetected and Quantified21.0 +/- 2.8 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
UrineDetected and Quantified11.851 +/- 17.07 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.2423 +/- 1.4785 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected and Quantified1.0274 +/- 0.8653 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Intestinal failure
  1. Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. [PubMed:11113071 ]
Epilepsy
  1. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
  2. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Argininosuccinic aciduria
  1. Kleijer WJ, Garritsen VH, Linnebank M, Mooyer P, Huijmans JG, Mustonen A, Simola KO, Arslan-Kirchner M, Battini R, Briones P, Cardo E, Mandel H, Tschiedel E, Wanders RJ, Koch HG: Clinical, enzymatic, and molecular genetic characterization of a biochemical variant type of argininosuccinic aciduria: prenatal and postnatal diagnosis in five unrelated families. J Inherit Metab Dis. 2002 Sep;25(5):399-410. [PubMed:12408190 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Fumarase deficiency
  1. Allegri G, Fernandes MJ, Scalco FB, Correia P, Simoni RE, Llerena JC Jr, de Oliveira ML: Fumaric aciduria: an overview and the first Brazilian case report. J Inherit Metab Dis. 2010 Aug;33(4):411-9. doi: 10.1007/s10545-010-9134-2. Epub 2010 Jun 15. [PubMed:20549362 ]
N-acetylglutamate synthetase deficiency
  1. Guffon N, Vianey-Saban C, Bourgeois J, Rabier D, Colombo JP, Guibaud P: A new neonatal case of N-acetylglutamate synthase deficiency treated by carbamylglutamate. J Inherit Metab Dis. 1995;18(1):61-5. [PubMed:7623444 ]
Citrullinemia type I
  1. Kose E, Unal O, Bulbul S, Gunduz M, Haberle J, Arslan N: Identification of three novel mutations in fourteen patients with citrullinemia type 1. Clin Biochem. 2017 Aug;50(12):686-689. doi: 10.1016/j.clinbiochem.2017.01.011. Epub 2017 Jan 27. [PubMed:28132756 ]
Citrullinemia type II, adult-onset
  1. Komatsu M, Yazaki M, Tanaka N, Sano K, Hashimoto E, Takei Y, Song YZ, Tanaka E, Kiyosawa K, Saheki T, Aoyama T, Kobayashi K: Citrin deficiency as a cause of chronic liver disorder mimicking non-alcoholic fatty liver disease. J Hepatol. 2008 Nov;49(5):810-20. doi: 10.1016/j.jhep.2008.05.016. Epub 2008 Jun 10. [PubMed:18620775 ]
Pearson Syndrome
  1. Crippa BL, Leon E, Calhoun A, Lowichik A, Pasquali M, Longo N: Biochemical abnormalities in Pearson syndrome. Am J Med Genet A. 2015 Mar;167A(3):621-8. doi: 10.1002/ajmg.a.36939. [PubMed:25691415 ]
Citrullinemia type II, neonatal-onset
  1. Ohura T, Kobayashi K, Tazawa Y, Nishi I, Abukawa D, Sakamoto O, Iinuma K, Saheki T: Neonatal presentation of adult-onset type II citrullinemia. Hum Genet. 2001 Feb;108(2):87-90. [PubMed:11281457 ]
Cutis laxa, autosomal recessive, type IIIA
  1. Baumgartner MR, Hu CA, Almashanu S, Steel G, Obie C, Aral B, Rabier D, Kamoun P, Saudubray JM, Valle D: Hyperammonemia with reduced ornithine, citrulline, arginine and proline: a new inborn error caused by a mutation in the gene encoding delta(1)-pyrroline-5-carboxylate synthase. Hum Mol Genet. 2000 Nov 22;9(19):2853-8. [PubMed:11092761 ]
Myopathy, lactic acidosis, and sideroblastic anemia 1
  1. Parfait B, de Lonlay P, von Kleist-Retzow JC, Cormier-Daire V, Chretien D, Rotig A, Rabier D, Saudubray JM, Rustin P, Munnich A: The neurogenic weakness, ataxia and retinitis pigmentosa (NARP) syndrome mtDNA mutation (T8993G) triggers muscle ATPase deficiency and hypocitrullinaemia. Eur J Pediatr. 1999 Jan;158(1):55-8. [PubMed:9950309 ]
Phosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic
  1. Vieira P, Cameron J, Rahikkala E, Keski-Filppula R, Zhang LH, Santra S, Matthews A, Myllynen P, Nuutinen M, Moilanen JS, Rodenburg RJ, Rolfs A, Uusimaa J, van Karnebeek CDM: Novel homozygous PCK1 mutation causing cytosolic phosphoenolpyruvate carboxykinase deficiency presenting as childhood hypoglycemia, an abnormal pattern of urine metabolites and liver dysfunction. Mol Genet Metab. 2017 Apr;120(4):337-341. doi: 10.1016/j.ymgme.2017.02.003. Epub 2017 Feb 6. [PubMed:28216384 ]
  2. Santra S, Cameron JM, Shyr C, Zhang L, Drogemoller B, Ross CJ, Wasserman WW, Wevers RA, Rodenburg RJ, Gupte G, Preece MA, van Karnebeek CD: Cytosolic phosphoenolpyruvate carboxykinase deficiency presenting with acute liver failure following gastroenteritis. Mol Genet Metab. 2016 May;118(1):21-7. doi: 10.1016/j.ymgme.2016.03.001. Epub 2016 Mar 4. [PubMed:26971250 ]
Schizophrenia
  1. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Gout
  1. Shao T, Shao L, Li H, Xie Z, He Z, Wen C: Combined Signature of the Fecal Microbiome and Metabolome in Patients with Gout. Front Microbiol. 2017 Feb 21;8:268. doi: 10.3389/fmicb.2017.00268. eCollection 2017. [PubMed:28270806 ]
Rheumatoid arthritis
  1. Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 104300 (Alzheimer's disease)
  • 207900 (Argininosuccinic aciduria)
  • 606812 (Fumarase deficiency)
  • 608300 (N-acetylglutamate synthetase deficiency)
  • 215700 (Citrullinemia type I)
  • 603471 (Citrullinemia type II, adult-onset)
  • 557000 (Pearson Syndrome)
  • 605814 (Citrullinemia type II, neonatal-onset)
  • 219150 (Cutis laxa, autosomal recessive, type IIIA)
  • 600462 (Myopathy, lactic acidosis, and sideroblastic anemia 1)
  • 261680 (Phosphoenolpyruvate Carboxykinase Deficiency 1, Cytosolic)
  • 181500 (Schizophrenia)
  • 114500 (Colorectal cancer)
  • 266600 (Crohn's disease)
  • 138900 (Gout)
  • 180300 (Rheumatoid arthritis)
  • 260350 (Pancreatic cancer)
  • 170650 (Periodontal disease)
  • 600274 (Frontotemporal dementia)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB00155
Phenol Explorer Compound IDNot Available
FooDB IDFDB011841
KNApSAcK IDC00001348
Chemspider ID9367
KEGG Compound IDC00327
BioCyc IDL-CITRULLINE
BiGG ID34627
Wikipedia LinkCitrulline
METLIN ID16
PubChem Compound9750
PDB IDNot Available
ChEBI ID16349
Food Biomarker OntologyNot Available
VMH IDCITR_L
MarkerDB IDMDB00000279
Good Scents IDNot Available
References
Synthesis ReferenceKakimoto, Toshio; Shibatani, Takeji; Nishimura, Noriyuki; Chibata, Ichiro. Enzymic production of L-citrulline by Pseudomonas putida. Applied Microbiology (1971), 22(6), 992-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
  3. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
  4. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
  5. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
  6. Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. [PubMed:9267323 ]
  7. Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. [PubMed:11113071 ]
  8. Melis GC, Boelens PG, van der Sijp JR, Popovici T, De Bandt JP, Cynober L, van Leeuwen PA: The feeding route (enteral or parenteral) affects the plasma response of the dipetide Ala-Gln and the amino acids glutamine, citrulline and arginine, with the administration of Ala-Gln in preoperative patients. Br J Nutr. 2005 Jul;94(1):19-26. [PubMed:16115328 ]
  9. DeLong GR, Glick TH: Ammonia metabolism in Reye syndrome and the effect of citrulline. Ann Neurol. 1982 Jan;11(1):53-8. [PubMed:7059128 ]
  10. Jianfeng G, Weiming Z, Ning L, Fangnan L, Li T, Nan L, Jieshou L: Serum citrulline is a simple quantitative marker for small intestinal enterocytes mass and absorption function in short bowel patients. J Surg Res. 2005 Aug;127(2):177-82. [PubMed:15921697 ]
  11. Liappis N, Pohl B, Weber HP, el-Karkani H: [Free amino acids in the saliva of children with phenylketonuria]. Klin Padiatr. 1986 Jan-Feb;198(1):25-8. [PubMed:3959486 ]
  12. Fleisher LD, Harris CJ, Mitchell DA, Nadler HL: Citrullinemia: prenatal diagnosis of an affected fetus. Am J Hum Genet. 1983 Jan;35(1):85-90. [PubMed:6823975 ]
  13. Potter MA, Zeesman S, Brennan B, Kobayashi K, Gao HZ, Tabata A, Saheki T, Whelan DT: Pregnancy in a healthy woman with untreated citrullinemia. Am J Med Genet A. 2004 Aug 15;129A(1):77-82. [PubMed:15266621 ]
  14. Wheatley DN, Kilfeather R, Stitt A, Campbell E: Integrity and stability of the citrulline-arginine pathway in normal and tumour cell lines. Cancer Lett. 2005 Sep 28;227(2):141-52. [PubMed:16112417 ]
  15. Reparon-Schuijt CC, van Esch WJ, van Kooten C, Schellekens GA, de Jong BA, van Venrooij WJ, Breedveld FC, Verweij CL: Secretion of anti-citrulline-containing peptide antibody by B lymphocytes in rheumatoid arthritis. Arthritis Rheum. 2001 Jan;44(1):41-7. [PubMed:11212174 ]
  16. Maruyama H, Ogawa M, Nishio T, Kobayashi K, Saheki T, Sunohara N: Citrullinemia type II in a 64-year-old man with fluctuating serum citrulline levels. J Neurol Sci. 2001 Jan 1;182(2):167-70. [PubMed:11137523 ]
  17. McLaurin J, Moscarello MA: The preparation of antibodies reactive against citrulline-containing charge isomers of myelin basic protein but not against the arginine-containing charge isomers. Anal Biochem. 1990 Dec;191(2):272-7. [PubMed:1707596 ]
  18. Facchinetti F, Longo M, Piccinini F, Neri I, Volpe A: L-arginine infusion reduces blood pressure in preeclamptic women through nitric oxide release. J Soc Gynecol Investig. 1999 Jul-Aug;6(4):202-7. [PubMed:10486782 ]
  19. Origuchi Y, Ushijima T, Sakaguchi M, Akaboshi I, Matsuda I: Citrullinemia presenting as uncontrollable epilepsy. Brain Dev. 1984;6(3):328-31. [PubMed:6486381 ]
  20. Booth FA, Haworth JC, Dilling LA, Perry TL, Greenberg CR, Seargeant LE, Penn AM, Rhead WJ: Mitochondrial encephalomyopathy with associated aminoacidopathy in a male sibship. J Pediatr. 1989 Jul;115(1):81-8. [PubMed:2738799 ]
  21. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  22. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Argininosuccinate synthase
General function:
Involved in argininosuccinate synthase activity
Specific function:
Not Available
Gene Name:
ASS1
Uniprot ID:
P00966
Molecular weight:
46530.055
Reactions
Adenosine triphosphate + Citrulline + L-Aspartic acid → Adenosine monophosphate + Pyrophosphate + Argininosuccinic aciddetails
Adenosine triphosphate + Citrulline + L-Aspartic acid → Adenosine monophosphate + Pyrophosphate + Argininosuccinic aciddetails
References
  1. Braissant O, Honegger P, Loup M, Iwase K, Takiguchi M, Bachmann C: Hyperammonemia: regulation of argininosuccinate synthetase and argininosuccinate lyase genes in aggregating cell cultures of fetal rat brain. Neurosci Lett. 1999 May 7;266(2):89-92. [PubMed:10353334 ]
  2. Braissant O, Gotoh T, Loup M, Mori M, Bachmann C: L-arginine uptake, the citrulline-NO cycle and arginase II in the rat brain: an in situ hybridization study. Brain Res Mol Brain Res. 1999 Jul 5;70(2):231-41. [PubMed:10407171 ]
  3. Keilhoff G, Reiser M, Stanarius A, Aoki E, Wolf G: Citrulline immunohistochemistry for demonstration of NOS activity in vivo and in vitro. Nitric Oxide. 2000 Aug;4(4):343-53. [PubMed:10944418 ]
  4. Zhang B, Cao GL, Domachowske J, Jackson MJ, Porasuphatana S, Rosen GM: Stable expression of varied levels of inducible nitric oxide synthase in primary cultures of endothelial cells. Anal Biochem. 2000 Nov 15;286(2):198-205. [PubMed:11067741 ]
  5. Zhang WY, Gotoh T, Oyadomari S, Mori M: Coinduction of inducible nitric oxide synthase and arginine recycling enzymes in cytokine-stimulated PC12 cells and high output production of nitric oxide. Brain Res Mol Brain Res. 2000 Nov 10;83(1-2):1-8. [PubMed:11072090 ]
Enzyme Details
2. Protein-arginine deiminase type-6
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the deimination of arginine residues of proteins. May be involved in cytoskeletal reorganization in the egg and early embryo (By similarity).
Gene Name:
PADI6
Uniprot ID:
Q6TGC4
Molecular weight:
77726.735
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
3. Protein-arginine deiminase type-4
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the citrullination/deimination of arginine residues of proteins. Citrullinates histone H3 at 'Arg-8' and/or 'Arg-17' and histone H4 at 'Arg-3', which prevents their methylation by CARM1 and HRMT1L2/PRMT1 and represses transcription. Citrullinates EP300/P300 at 'Arg-2142', which favors its interaction with NCOA2/GRIP1.
Gene Name:
PADI4
Uniprot ID:
Q9UM07
Molecular weight:
74078.65
References
  1. Wang Y, Wysocka J, Sayegh J, Lee YH, Perlin JR, Leonelli L, Sonbuchner LS, McDonald CH, Cook RG, Dou Y, Roeder RG, Clarke S, Stallcup MR, Allis CD, Coonrod SA: Human PAD4 regulates histone arginine methylation levels via demethylimination. Science. 2004 Oct 8;306(5694):279-83. Epub 2004 Sep 2. [PubMed:15345777 ]
  2. Wysocka J, Allis CD, Coonrod S: Histone arginine methylation and its dynamic regulation. Front Biosci. 2006 Jan 1;11:344-55. [PubMed:16146736 ]
  3. Yamamoto K, Yamada R: Genome-wide single nucleotide polymorphism analyses of rheumatoid arthritis. J Autoimmun. 2005;25 Suppl:12-5. Epub 2005 Nov 2. [PubMed:16271291 ]
  4. Chang X, Han J: Expression of peptidylarginine deiminase type 4 (PAD4) in various tumors. Mol Carcinog. 2006 Mar;45(3):183-96. [PubMed:16355400 ]
  5. Okazaki Y, Suzuki A, Sawada T, Ohtake-Yamanaka M, Inoue T, Hasebe T, Yamada R, Yamamoto K: Identification of citrullinated eukaryotic translation initiation factor 4G1 as novel autoantigen in rheumatoid arthritis. Biochem Biophys Res Commun. 2006 Mar 3;341(1):94-100. Epub 2006 Jan 6. [PubMed:16412378 ]
Enzyme Details
4. Protein-arginine deiminase type-3
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the deimination of arginine residues of proteins.
Gene Name:
PADI3
Uniprot ID:
Q9ULW8
Molecular weight:
74742.705
References
  1. Dong S, Kanno T, Yamaki A, Kojima T, Shiraiwa M, Kawada A, Mechin MC, Chavanas S, Serre G, Simon M, Takahara H: NF-Y and Sp1/Sp3 are involved in the transcriptional regulation of the peptidylarginine deiminase type III gene (PADI3) in human keratinocytes. Biochem J. 2006 Aug 1;397(3):449-59. [PubMed:16671893 ]
  2. Iida A, Nakamura Y: Identification of 45 novel SNPs in the 83-kb region containing peptidylarginine deiminase types 1 and 3 loci on chromosomal band 1p36.13. J Hum Genet. 2004;49(7):387-90. Epub 2004 May 19. [PubMed:15150696 ]
  3. Kanno T, Kawada A, Yamanouchi J, Yosida-Noro C, Yoshiki A, Shiraiwa M, Kusakabe M, Manabe M, Tezuka T, Takahara H: Human peptidylarginine deiminase type III: molecular cloning and nucleotide sequence of the cDNA, properties of the recombinant enzyme, and immunohistochemical localization in human skin. J Invest Dermatol. 2000 Nov;115(5):813-23. [PubMed:11069618 ]
Enzyme Details
5. Protein-arginine deiminase type-2
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the deimination of arginine residues of proteins (By similarity).
Gene Name:
PADI2
Uniprot ID:
Q9Y2J8
Molecular weight:
75563.35
References
  1. Dong S, Kojima T, Shiraiwa M, Mechin MC, Chavanas S, Serre G, Simon M, Kawada A, Takahara H: Regulation of the expression of peptidylarginine deiminase type II gene (PADI2) in human keratinocytes involves Sp1 and Sp3 transcription factors. J Invest Dermatol. 2005 May;124(5):1026-33. [PubMed:15854045 ]
Enzyme Details
6. Protein-arginine deiminase type-1
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the deimination of arginine residues of proteins (By similarity).
Gene Name:
PADI1
Uniprot ID:
Q9ULC6
Molecular weight:
74664.97
References
  1. Iida A, Nakamura Y: Identification of 45 novel SNPs in the 83-kb region containing peptidylarginine deiminase types 1 and 3 loci on chromosomal band 1p36.13. J Hum Genet. 2004;49(7):387-90. Epub 2004 May 19. [PubMed:15150696 ]
Enzyme Details
7. N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH1
Uniprot ID:
O94760
Molecular weight:
20189.135
Reactions
Asymmetric dimethylarginine + Water → Dimethylamine + Citrullinedetails
References
  1. Mishima T, Hamada T, Ui-Tei K, Takahashi F, Miyata Y, Imaki J, Suzuki H, Yamashita K: Expression of DDAH1 in chick and rat embryos. Brain Res Dev Brain Res. 2004 Feb 20;148(2):223-32. [PubMed:14766200 ]
  2. Tran CT, Fox MF, Vallance P, Leiper JM: Chromosomal localization, gene structure, and expression pattern of DDAH1: comparison with DDAH2 and implications for evolutionary origins. Genomics. 2000 Aug 15;68(1):101-5. [PubMed:10950934 ]
  3. Arrigoni FI, Vallance P, Haworth SG, Leiper JM: Metabolism of asymmetric dimethylarginines is regulated in the lung developmentally and with pulmonary hypertension induced by hypobaric hypoxia. Circulation. 2003 Mar 4;107(8):1195-201. [PubMed:12615801 ]
Enzyme Details
8. N(G),N(G)-dimethylarginine dimethylaminohydrolase 2
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amidines
Specific function:
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name:
DDAH2
Uniprot ID:
O95865
Molecular weight:
29643.54
Reactions
Asymmetric dimethylarginine + Water → Dimethylamine + Citrullinedetails
References
  1. Tran CT, Fox MF, Vallance P, Leiper JM: Chromosomal localization, gene structure, and expression pattern of DDAH1: comparison with DDAH2 and implications for evolutionary origins. Genomics. 2000 Aug 15;68(1):101-5. [PubMed:10950934 ]
  2. Tain YL, Baylis C: Determination of dimethylarginine dimethylaminohydrolase activity in the kidney. Kidney Int. 2007 Oct;72(7):886-9. Epub 2007 Jul 25. [PubMed:17653133 ]
Enzyme Details
9. Nitric oxide synthase, inducible
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
Reactions
L-Arginine + NADPH + Oxygen → Citrulline + Nitric oxide + NADP + Waterdetails
NADPH + N(omega)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → Nitric oxide + Citrulline + NADP + Waterdetails
References
  1. Cunningham JM, Rayne RC: Radiochemical measurement of NOS activity by conversion of [14C]L-arginine to citrulline using HPLC separation. Methods Mol Biol. 1998;100:75-81. [PubMed:10906995 ]
  2. Keilhoff G, Reiser M, Stanarius A, Aoki E, Wolf G: Citrulline immunohistochemistry for demonstration of NOS activity in vivo and in vitro. Nitric Oxide. 2000 Aug;4(4):343-53. [PubMed:10944418 ]
  3. Conrad KP, Powers RW, Davis AK, Novak J: Citrulline is not the major product using the standard "NOS activity" assay on renal cortical homogenates. Am J Physiol Regul Integr Comp Physiol. 2002 Jan;282(1):R303-10. [PubMed:11742852 ]
  4. Knowles RG, Salter M: Measurement of NOS activity by conversion of radiolabeled arginine to citrulline using ion-exchange separation. Methods Mol Biol. 1998;100:67-73. [PubMed:10906994 ]
  5. Yi GB, McClendon D, Desaiah D, Goddard J, Lister A, Moffitt J, Meer RK, deShazo R, Lee KS, Rockhold RW: Fire ant venom alkaloid, isosolenopsin A, a potent and selective inhibitor of neuronal nitric oxide synthase. Int J Toxicol. 2003 Mar-Apr;22(2):81-6. [PubMed:12745988 ]
Enzyme Details
10. Ornithine carbamoyltransferase, mitochondrial
General function:
Involved in carboxyl- or carbamoyltransferase activity
Specific function:
Not Available
Gene Name:
OTC
Uniprot ID:
P00480
Molecular weight:
39934.775
Reactions
Carbamoyl phosphate + Ornithine → Phosphate + Citrullinedetails
References
  1. Quintero MJ, Muro-Pastor AM, Herrero A, Flores E: Arginine catabolism in the cyanobacterium Synechocystis sp. Strain PCC 6803 involves the urea cycle and arginase pathway. J Bacteriol. 2000 Feb;182(4):1008-15. [PubMed:10648527 ]
  2. Morizono H, Cabrera-Luque J, Shi D, Gallegos R, Yamaguchi S, Yu X, Allewell NM, Malamy MH, Tuchman M: Acetylornithine transcarbamylase: a novel enzyme in arginine biosynthesis. J Bacteriol. 2006 Apr;188(8):2974-82. [PubMed:16585758 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters