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Showing metabocard for N-Acetylmethionine sulfoxide (HMDB0240343)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 16:09:12 UTC
Update Date2022-09-22 18:34:32 UTC
HMDB IDHMDB0240343
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetylmethionine sulfoxide
DescriptionN-Acetylmethionine sulfoxide (CAS: 3054-51-1), also known as N-ACMSO or 2-(acetylamino)-4-(methylsulfinyl)butanoic acid, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetylmethionine sulfoxide has been identified in the human placenta (PMID: 32033212 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0240343 (N-Acetylmethionine sulfoxide)

  Mrv1652311141922232D          

 13 12  0  0  0  0            999 V2000
 9992.2282 9991.9348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.5146 9992.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8001 9991.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0857 9992.3473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3670 9991.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0857 9993.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2282 9991.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9990.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6576 9991.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9989.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9992.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6576 9991.9348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9993.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  1  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
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3D MOL for HMDB0240343 (N-Acetylmethionine sulfoxide)

HMDB0240343
     RDKit          3D
N-Acetylmethionine sulfoxide
 26 25  0  0  0  0  0  0  0  0999 V2000
    4.0184    0.7548   -1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6783    1.0910   -1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    2.1589   -1.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212    0.1984   -0.2223 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090    0.5351    0.3127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2464   -0.5246   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -0.3059    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910   -1.6135   -0.3491 S   0  0  0  0  0  4  0  0  0  0  0  0
   -4.3929   -1.4218    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5502   -1.7729   -1.8401 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    0.6216    1.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980    0.3906    2.3498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621    0.9495    2.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9742   -0.2871   -2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636    1.4314   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    0.8856   -0.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -0.6943    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950    1.5338   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1777   -0.5539   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -1.5105    0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9951    0.6991    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -0.4365    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7800   -0.3999    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0098   -2.1834   -0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4409   -1.6452    1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    0.3919    3.4225 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  2  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  6
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 13 26  1  0
M  END
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3D SDF for HMDB0240343 (N-Acetylmethionine sulfoxide)

  Mrv1652311141922232D          

 13 12  0  0  0  0            999 V2000
 9992.2282 9991.9348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9991.5146 9992.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8001 9991.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0857 9992.3473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3670 9991.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.0857 9993.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2282 9991.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9990.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6576 9991.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9989.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9992.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6576 9991.9348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9439 9993.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  1  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240343

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1

> <INCHI_KEY>
NPIMMZJBURSMON-YLTHGKPTSA-N

> <FORMULA>
C7H13NO4S

> <MOLECULAR_WEIGHT>
207.24

> <EXACT_MASS>
207.056529077

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.13034442603751

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-acetamido-4-methanesulfinylbutanoic acid

> <ALOGPS_LOGP>
-0.96

> <JCHEM_LOGP>
-2.4839143003333333

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.169773016336855

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4502696397505304

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8007818606917136

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
48.78650000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-acetamido-4-methanesulfinylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0240343 (N-Acetylmethionine sulfoxide)

HMDB0240343
     RDKit          3D
N-Acetylmethionine sulfoxide
 26 25  0  0  0  0  0  0  0  0999 V2000
    4.0184    0.7548   -1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6783    1.0910   -1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1345    2.1589   -1.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212    0.1984   -0.2223 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090    0.5351    0.3127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2464   -0.5246   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -0.3059    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910   -1.6135   -0.3491 S   0  0  0  0  0  4  0  0  0  0  0  0
   -4.3929   -1.4218    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5502   -1.7729   -1.8401 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    0.6216    1.7733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980    0.3906    2.3498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621    0.9495    2.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9742   -0.2871   -2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636    1.4314   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    0.8856   -0.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4475   -0.6943    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950    1.5338   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1777   -0.5539   -1.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -1.5105    0.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9951    0.6991    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712   -0.4365    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7800   -0.3999    0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0098   -2.1834   -0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4409   -1.6452    1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4377    0.3919    3.4225 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  2  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  6
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 13 26  1  0
M  END
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PDB for HMDB0240343 (N-Acetylmethionine sulfoxide)

HEADER    PROTEIN                                 14-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-NOV-19         0                                  
HETATM    1  C   UNK     0    8652.1598651.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8650.8278652.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8649.4938651.612   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0    8648.1608652.382   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0    8646.8188651.612   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8648.1608653.922   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8652.1598650.073   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8653.4958649.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8654.8288650.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8653.4958647.762   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8653.4958652.382   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8654.8288651.612   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8653.4958653.922   0.000  0.00  0.00           O+0
CONECT    1    2    7   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for HMDB0240343 (N-Acetylmethionine sulfoxide)

COMPND    HMDB0240343
HETATM    1  C1  UNL     1       4.018   0.755  -1.663  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.678   1.091  -1.112  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.134   2.159  -1.434  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.021   0.198  -0.222  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.709   0.535   0.313  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.246  -0.525  -0.172  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.643  -0.306   0.300  1.00  0.00           C  
HETATM    8  S1  UNL     1      -2.691  -1.614  -0.349  1.00  0.00           S  
HETATM    9  C6  UNL     1      -4.393  -1.422   0.176  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.550  -1.773  -1.840  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.802   0.622   1.773  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.898   0.391   2.350  1.00  0.00           O  
HETATM   13  O4  UNL     1      -0.262   0.949   2.580  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.974  -0.287  -2.048  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.264   1.431  -2.499  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.787   0.886  -0.885  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.447  -0.694   0.063  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.395   1.534  -0.098  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.178  -0.554  -1.284  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.169  -1.510   0.183  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.995   0.699   0.080  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.671  -0.437   1.412  1.00  0.00           H  
HETATM   23  H10 UNL     1      -4.780  -0.400   0.040  1.00  0.00           H  
HETATM   24  H11 UNL     1      -5.010  -2.183  -0.343  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.441  -1.645   1.256  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.438   0.392   3.422  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6   11   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   10   10
CONECT    9   23   24   25
CONECT   11   12   12   13
CONECT   13   26
END
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SMILES for HMDB0240343 (N-Acetylmethionine sulfoxide)

CC(=O)N[C@@H](CCS(C)=O)C(O)=O
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INCHI for HMDB0240343 (N-Acetylmethionine sulfoxide)

InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
N-Acetylmethionine sulphoxideGenerator
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulfinylbutanoateHMDB
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoateHMDB
(2S)-2-[(1-Hydroxyethylidene)amino]-4-methanesulphinylbutanoic acidHMDB
N-ACMSOHMDB
(2S)-2-(Acetylamino)-4-(methylsulfinyl)butanoic acidHMDB
(2S)-2-Acetamido-4-(methylsulfinyl)butanoic acidHMDB
(2S)-2-Acetamido-4-methanesulfinylbutanoic acidHMDB
(2S)-2-Acetamido-4-methylsulfinylbutanoic acidHMDB
2-(Acetylamino)-4-(methylsulfinyl)butanoic acidHMDB
N-Acetyl-L-methionine sulfoxideHMDB
N-Acetylmethionine sulfoxideMeSH
Chemical FormulaC7H13NO4S
Average Molecular Weight207.24
Monoisotopic Molecular Weight207.056529077
IUPAC Name(2S)-2-acetamido-4-methanesulfinylbutanoic acid
Traditional Name(2S)-2-acetamido-4-methanesulfinylbutanoic acid
CAS Registry Number108646-71-5
SMILES
CC(=O)N[C@@H](CCS(C)=O)C(O)=O
InChI Identifier
InChI=1S/C7H13NO4S/c1-5(9)8-6(7(10)11)3-4-13(2)12/h6H,3-4H2,1-2H3,(H,8,9)(H,10,11)/t6-,13?/m0/s1
InChI KeyNPIMMZJBURSMON-YLTHGKPTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated 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 ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Sulfoxide
  • Sulfinyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19354090
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7408371
PDB IDNot Available
ChEBI IDNot Available
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. 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 ]