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Showing metabocard for Glycylvaline (HMDB0028854)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:45 UTC
Update Date2023-02-21 17:18:37 UTC
HMDB IDHMDB0028854
Secondary Accession Numbers
  • HMDB28854
Metabolite Identification
Common NameGlycylvaline
DescriptionGlycylvaline, also known as GV or gly-L-val, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Glycylvaline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make glycylvaline a potential biomarker for the consumption of these foods. Glycylvaline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Glycylvaline.
Structure
Data?1676999917
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0028854 (Glycylvaline)


  Mrv1652304062013432D          

 12 11  0  0  0  0            999 V2000
 9987.5362 9988.3060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.5362 9987.4820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9987.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9660 9987.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6796 9987.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9986.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8217 9988.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1072 9988.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8217 9989.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9988.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9660 9988.3060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9989.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for HMDB0028854 (Glycylvaline)

HMDB0028854
     RDKit          3D
Glycylvaline
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.7624    0.1764    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4052    0.7310    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    1.2924   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -0.4285    0.5149 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8902   -0.0618    0.1246 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -0.2131    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070   -0.6938    2.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.1560    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505    0.6776   -0.7547 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -1.5386   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175   -2.0090   -1.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972   -2.0796   -0.1890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.9855    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256   -0.6594    1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3728   -0.0568    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    1.4694    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672    2.2798   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6415    1.3696   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3222    0.6243   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406   -0.8310    1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0462    0.3318   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -0.7398    0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    0.8540    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -0.0527   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    1.4069   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307   -2.9907    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
M  END
Download

3D SDF for HMDB0028854 (Glycylvaline)


  Mrv1652304062013432D          

 12 11  0  0  0  0            999 V2000
 9987.5362 9988.3060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.5362 9987.4820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9987.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9660 9987.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.6796 9987.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9986.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8217 9988.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1072 9988.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8217 9989.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9988.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.9660 9988.3060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.2502 9989.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0028854

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@H](NC(=O)CN)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O3/c1-4(2)6(7(11)12)9-5(10)3-8/h4,6H,3,8H2,1-2H3,(H,9,10)(H,11,12)/t6-/m0/s1

> <INCHI_KEY>
STKYPAFSDFAEPH-LURJTMIESA-N

> <FORMULA>
C7H14N2O3

> <MOLECULAR_WEIGHT>
174.2

> <EXACT_MASS>
174.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.58699599901992

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(2-aminoacetamido)-3-methylbutanoic acid

> <ALOGPS_LOGP>
-2.54

> <JCHEM_LOGP>
-3.0606575357418633

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.77868029477095

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8116975726339217

> <JCHEM_PKA_STRONGEST_BASIC>
8.139565149280257

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
42.296400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gly-val

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0028854 (Glycylvaline)

HMDB0028854
     RDKit          3D
Glycylvaline
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.7624    0.1764    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4052    0.7310    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5942    1.2924   -0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -0.4285    0.5149 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8902   -0.0618    0.1246 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0102   -0.2131    0.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070   -0.6938    2.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3757    0.1560    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505    0.6776   -0.7547 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -1.5386   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175   -2.0090   -1.2644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972   -2.0796   -0.1890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2960    0.9855    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256   -0.6594    1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3728   -0.0568    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    1.4694    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672    2.2798   -0.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6415    1.3696   -1.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3222    0.6243   -1.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406   -0.8310    1.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0462    0.3318   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -0.7398    0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000    0.8540    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -0.0527   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    1.4069   -0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307   -2.9907    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
M  END
Download

PDB for HMDB0028854 (Glycylvaline)

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8643.4018644.838   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8643.4018643.300   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8644.7348642.528   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8646.0708643.300   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8647.4028642.528   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0    8644.7348640.988   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8642.0678645.608   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8640.7338644.838   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8642.0678647.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8644.7348645.608   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8646.0708644.838   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8644.7348647.148   0.000  0.00  0.00           O+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0028854 (Glycylvaline)

COMPND    HMDB0028854
HETATM    1  C1  UNL     1      -2.762   0.176   0.930  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.405   0.731   0.494  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.594   1.292  -0.894  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.441  -0.429   0.515  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.890  -0.062   0.125  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.010  -0.213   0.980  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.807  -0.694   2.132  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.376   0.156   0.598  1.00  0.00           C  
HETATM    9  N2  UNL     1       3.350   0.678  -0.755  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.944  -1.539  -0.352  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.217  -2.009  -1.264  1.00  0.00           O  
HETATM   12  O3  UNL     1      -2.197  -2.080  -0.189  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.296   0.986   1.477  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.626  -0.659   1.617  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.373  -0.057   0.040  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.080   1.469   1.229  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.067   2.280  -0.794  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.642   1.370  -1.453  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.322   0.624  -1.440  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.441  -0.831   1.551  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.046   0.332  -0.823  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.029  -0.740   0.578  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.800   0.854   1.321  1.00  0.00           H  
HETATM   24  H12 UNL     1       3.342  -0.053  -1.472  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.086   1.407  -0.899  1.00  0.00           H  
HETATM   26  H14 UNL     1      -2.331  -2.991   0.234  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5   10   20
CONECT    5    6   21
CONECT    6    7    7    8
CONECT    8    9   22   23
CONECT    9   24   25
CONECT   10   11   11   12
CONECT   12   26
END
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SMILES for HMDB0028854 (Glycylvaline)

CC(C)[C@H](NC(=O)CN)C(O)=O
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INCHI for HMDB0028854 (Glycylvaline)

InChI=1S/C7H14N2O3/c1-4(2)6(7(11)12)9-5(10)3-8/h4,6H,3,8H2,1-2H3,(H,9,10)(H,11,12)/t6-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Gly-L-valChEBI
Glycyl-valineChEBI
GVChEBI
Glycylvaline, (L)-isomerHMDB
Glycylvaline, (D)-isomerHMDB
Gly-valHMDB
g-V DipeptideHMDB
GV DipeptideHMDB
Glycine valine dipeptideHMDB
Glycine-valine dipeptideHMDB
Glycyl-L-valineHMDB
N-Glycyl-L-valineHMDB
N-GlycylvalineHMDB
GlycylvalineChEBI
Chemical FormulaC7H14N2O3
Average Molecular Weight174.2
Monoisotopic Molecular Weight174.100442319
IUPAC Name(2S)-2-(2-aminoacetamido)-3-methylbutanoic acid
Traditional Namegly-val
CAS Registry Number1963-21-9
SMILES
CC(C)[C@H](NC(=O)CN)C(O)=O
InChI Identifier
InChI=1S/C7H14N2O3/c1-4(2)6(7(11)12)9-5(10)3-8/h4,6H,3,8H2,1-2H3,(H,9,10)(H,11,12)/t6-/m0/s1
InChI KeySTKYPAFSDFAEPH-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Valine or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Amino acid
  • Carboxamide group
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.06Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility34.2 g/LALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)3.81ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity42.3 m³·mol⁻¹ChemAxon
Polarizability17.59 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
DeepCCS[M+H]+137.39430932474
DeepCCS[M-H]-134.08830932474
DeepCCS[M-2H]-171.05430932474
DeepCCS[M+Na]+146.59230932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.4 minutes32390414
Predicted by Siyang on May 30, 20229.5504 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.69 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid306.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid693.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid276.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid62.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid162.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid46.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid275.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid251.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)588.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid603.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid126.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid784.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid165.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid178.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate459.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA417.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water232.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlycylvalineCC(C)[C@H](NC(=O)CN)C(O)=O2368.9Standard polar33892256
GlycylvalineCC(C)[C@H](NC(=O)CN)C(O)=O1520.3Standard non polar33892256
GlycylvalineCC(C)[C@H](NC(=O)CN)C(O)=O1607.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycylvaline,1TMS,isomer #1CC(C)[C@H](NC(=O)CN)C(=O)O[Si](C)(C)C1615.3Semi standard non polar33892256
Glycylvaline,1TMS,isomer #2CC(C)[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O1659.3Semi standard non polar33892256
Glycylvaline,1TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN)[Si](C)(C)C1567.5Semi standard non polar33892256
Glycylvaline,2TMS,isomer #1CC(C)[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1705.6Semi standard non polar33892256
Glycylvaline,2TMS,isomer #1CC(C)[C@H](NC(=O)CN[Si](C)(C)C)C(=O)O[Si](C)(C)C1637.3Standard non polar33892256
Glycylvaline,2TMS,isomer #2CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN)[Si](C)(C)C1579.6Semi standard non polar33892256
Glycylvaline,2TMS,isomer #2CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN)[Si](C)(C)C1650.8Standard non polar33892256
Glycylvaline,2TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1672.3Semi standard non polar33892256
Glycylvaline,2TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1665.9Standard non polar33892256
Glycylvaline,2TMS,isomer #4CC(C)[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1851.1Semi standard non polar33892256
Glycylvaline,2TMS,isomer #4CC(C)[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O1728.6Standard non polar33892256
Glycylvaline,3TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1691.3Semi standard non polar33892256
Glycylvaline,3TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN[Si](C)(C)C)[Si](C)(C)C1740.9Standard non polar33892256
Glycylvaline,3TMS,isomer #2CC(C)[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1859.6Semi standard non polar33892256
Glycylvaline,3TMS,isomer #2CC(C)[C@H](NC(=O)CN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C1792.8Standard non polar33892256
Glycylvaline,3TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1817.6Semi standard non polar33892256
Glycylvaline,3TMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1813.5Standard non polar33892256
Glycylvaline,4TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1862.7Semi standard non polar33892256
Glycylvaline,4TMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C)N(C(=O)CN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1878.3Standard non polar33892256
Glycylvaline,1TBDMS,isomer #1CC(C)[C@H](NC(=O)CN)C(=O)O[Si](C)(C)C(C)(C)C1856.5Semi standard non polar33892256
Glycylvaline,1TBDMS,isomer #2CC(C)[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O1898.2Semi standard non polar33892256
Glycylvaline,1TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN)[Si](C)(C)C(C)(C)C1819.6Semi standard non polar33892256
Glycylvaline,2TBDMS,isomer #1CC(C)[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2121.7Semi standard non polar33892256
Glycylvaline,2TBDMS,isomer #1CC(C)[C@H](NC(=O)CN[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2046.3Standard non polar33892256
Glycylvaline,2TBDMS,isomer #2CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN)[Si](C)(C)C(C)(C)C2040.2Semi standard non polar33892256
Glycylvaline,2TBDMS,isomer #2CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN)[Si](C)(C)C(C)(C)C2025.3Standard non polar33892256
Glycylvaline,2TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2127.4Semi standard non polar33892256
Glycylvaline,2TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2052.9Standard non polar33892256
Glycylvaline,2TBDMS,isomer #4CC(C)[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2263.0Semi standard non polar33892256
Glycylvaline,2TBDMS,isomer #4CC(C)[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O2087.3Standard non polar33892256
Glycylvaline,3TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2359.6Semi standard non polar33892256
Glycylvaline,3TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2311.2Standard non polar33892256
Glycylvaline,3TBDMS,isomer #2CC(C)[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2485.0Semi standard non polar33892256
Glycylvaline,3TBDMS,isomer #2CC(C)[C@H](NC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2348.6Standard non polar33892256
Glycylvaline,3TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2481.0Semi standard non polar33892256
Glycylvaline,3TBDMS,isomer #3CC(C)[C@@H](C(=O)O)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2371.5Standard non polar33892256
Glycylvaline,4TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2712.7Semi standard non polar33892256
Glycylvaline,4TBDMS,isomer #1CC(C)[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2595.3Standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
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 but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
  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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111886
KNApSAcK IDNot Available
Chemspider ID2006926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724807
PDB IDNot Available
ChEBI ID73922
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Steininger R, Karner J, Roth E, Langer K: Infusion of dipeptides as nutritional substrates for glutamine, tyrosine, and branched-chain amino acids in patients with acute pancreatitis. Metabolism. 1989 Aug;38(8 Suppl 1):78-81. [PubMed:2503685 ]
  2. Guardiola J, De Felice M, Klopotowski T, Iaccarino M: Mutations affecting the different transport systems for isoleucine, leucine, and valine in Escherichia coli K-12. J Bacteriol. 1974 Feb;117(2):393-405. [PubMed:4590465 ]
  3. De Felice M, Guardiola J, Lamberti A, Iaccarino M: Escherichia coli K-12 mutants altered in the transport systems for oligo- and dipeptides. J Bacteriol. 1973 Nov;116(2):751-6. [PubMed:4126826 ]
  4. Zhang CX, Tong HB, Yan CG: First soluble multipolymer MPEG-supported liquid-phase convergent synthesis of tripeptide Fmoc-GlyVal-GlyOH. J Comb Chem. 2007 Nov-Dec;9(6):924-5. Epub 2007 Oct 31. [PubMed:17970597 ]
  5. SHELTON DC, NUTTER WE: UPTAKE OF VALINE AND GLYCYLVALINE BY LEUCONOSTOC MESENTEROIDES. J Bacteriol. 1964 Oct;88:1175-84. [PubMed:14219035 ]
  6. Huckle KR, Hutson DH, Millburn P: Species differences in the metabolism of 3-phenoxybenzoic acid. Drug Metab Dispos. 1981 Jul-Aug;9(4):352-9. [PubMed:6114835 ]
  7. Valenkevich LN: [Clinical importance of the determination of intestinal dipeptidase and enterokinase activity in patients with chronic enteritis]. Ter Arkh. 1987;59(11):88-90. [PubMed:3481658 ]
  8. Kline EL, Brown CS, Umbarger HE: Effect of a leu-linked mutation on the valine sensitivity of acetohydroxy acid synthase activity in Escherichia coli. J Bacteriol. 1975 Feb;121(2):491-6. [PubMed:1089631 ]
  9. Nath M, Pokharia S, Eng G, Song X, Kumar A: New triorganotin(IV) derivatives of dipeptides as anti-inflammatory-antimicrobial agents. Eur J Med Chem. 2005 Mar;40(3):289-98. Epub 2005 Jan 4. [PubMed:15725498 ]