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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:45:16 UTC

Update Date

2021-09-26 23:14:15 UTC

HMDB ID

HMDB0257715

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid

Description

6-hydroxy-2-[(1-hydroxyethylidene)amino]-2-(sulfanylmethyl)hex-3-enoic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on 6-hydroxy-2-[(1-hydroxyethylidene)amino]-2-(sulfanylmethyl)hex-3-enoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2r)-2-acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0257715
     RDKit          3D
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
   -2.9224    2.2672    1.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192    1.6198    0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762    2.3351    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    0.2285    0.7881 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.4839   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -0.2841    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    0.2000   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    0.3637    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -0.4594   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0436   -0.2844   -0.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735    0.0416   -1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.2340   -2.0540 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.9283   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -2.4358    0.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -2.7283   -0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713    3.0853    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    1.5687    2.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3702    2.6541    2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.3395    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771   -0.5689    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    0.4873   -1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.0554    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327    1.4141    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.0793   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928   -1.5172   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9693   -0.4165    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546    1.0789   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -0.5572   -2.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741   -1.5311   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -3.5522   -1.3535 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
M  END


  Mrv1652309112120452D          

 15 14  0  0  0  0            999 V2000
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  5  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257715

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC(CS)(C=CCCO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO4S/c1-7(12)10-9(6-15,8(13)14)4-2-3-5-11/h2,4,11,15H,3,5-6H2,1H3,(H,10,12)(H,13,14)

> <INCHI_KEY>
HICXXZOMOLMOII-UHFFFAOYSA-N

> <FORMULA>
C9H15NO4S

> <MOLECULAR_WEIGHT>
233.28

> <EXACT_MASS>
233.072179141

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.31787850163595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
-0.5095799446666671

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.98549649347131

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8321886640365306

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8111036512502943

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
58.99800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257715
     RDKit          3D
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
   -2.9224    2.2672    1.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192    1.6198    0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762    2.3351    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    0.2285    0.7881 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.4839   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -0.2841    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    0.2000   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    0.3637    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -0.4594   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0436   -0.2844   -0.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735    0.0416   -1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.2340   -2.0540 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.9283   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -2.4358    0.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -2.7283   -0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713    3.0853    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    1.5687    2.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3702    2.6541    2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.3395    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771   -0.5689    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    0.4873   -1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.0554    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327    1.4141    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.0793   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928   -1.5172   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9693   -0.4165    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546    1.0789   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -0.5572   -2.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741   -1.5311   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -3.5522   -1.3535 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       3.080   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.770   4.001   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.080   2.667   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -0.357   1.334   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.080  -2.667   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.644   0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.644  -0.976   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.977   1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    8   13                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0257715
HETATM    1  C1  UNL     1      -2.922   2.267   1.826  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.919   1.620   0.965  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.076   2.335   0.389  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.903   0.229   0.788  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.959  -0.484  -0.035  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.449  -0.284   0.398  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.399   0.200  -0.356  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.775   0.364   0.161  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.763  -0.459  -0.665  1.00  0.00           C  
HETATM   10  O2  UNL     1       5.044  -0.284  -0.155  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.073   0.042  -1.452  1.00  0.00           C  
HETATM   12  S1  UNL     1      -2.769  -0.234  -2.054  1.00  0.00           S  
HETATM   13  C9  UNL     1      -1.213  -1.928  -0.088  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.162  -2.436   0.534  1.00  0.00           O  
HETATM   15  O4  UNL     1      -0.385  -2.728  -0.839  1.00  0.00           O  
HETATM   16  H1  UNL     1      -3.471   3.085   1.315  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.686   1.569   2.215  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.370   2.654   2.725  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.622  -0.339   1.284  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.677  -0.569   1.418  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.188   0.487  -1.372  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.884   0.055   1.213  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.133   1.414   0.088  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.792  -0.079  -1.722  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.493  -1.517  -0.698  1.00  0.00           H  
HETATM   26  H11 UNL     1       4.969  -0.416   0.832  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.755   1.079  -1.550  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.392  -0.557  -2.125  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.174  -1.531  -1.687  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.713  -3.552  -1.353  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6   11   13
CONECT    6    7    7   20
CONECT    7    8   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   26
CONECT   11   12   27   28
CONECT   12   29
CONECT   13   14   14   15
CONECT   15   30
END

HMDB0257715
     RDKit          3D
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid
 30 29  0  0  0  0  0  0  0  0999 V2000
   -2.9224    2.2672    1.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192    1.6198    0.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762    2.3351    0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9027    0.2285    0.7881 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.4839   -0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -0.2841    0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    0.2000   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    0.3637    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -0.4594   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0436   -0.2844   -0.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735    0.0416   -1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.2340   -2.0540 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.9283   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1623   -2.4358    0.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853   -2.7283   -0.8389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713    3.0853    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    1.5687    2.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3702    2.6541    2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -0.3395    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771   -0.5689    1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    0.4873   -1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.0554    1.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327    1.4141    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7920   -0.0793   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4928   -1.5172   -0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9693   -0.4165    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7546    1.0789   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -0.5572   -2.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741   -1.5311   -1.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -3.5522   -1.3535 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  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Hydroxy-2-[(1-hydroxyethylidene)amino]-2-(sulfanylmethyl)hex-3-enoate	Generator
6-Hydroxy-2-[(1-hydroxyethylidene)amino]-2-(sulphanylmethyl)hex-3-enoate	Generator
6-Hydroxy-2-[(1-hydroxyethylidene)amino]-2-(sulphanylmethyl)hex-3-enoic acid	Generator
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoate	Generator
(2R)-2-Acetamido-6-hydroxy-2-(sulphanylmethyl)hex-3-enoate	Generator
(2R)-2-Acetamido-6-hydroxy-2-(sulphanylmethyl)hex-3-enoic acid	Generator

Chemical Formula

C₉H₁₅NO₄S

Average Molecular Weight

233.28

Monoisotopic Molecular Weight

233.072179141

IUPAC Name

2-acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid

Traditional Name

2-acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC(CS)(C=CCCO)C(O)=O

InChI Identifier

InChI=1S/C9H15NO4S/c1-7(12)10-9(6-15,8(13)14)4-2-3-5-11/h2,4,11,15H,3,5-6H2,1H3,(H,10,12)(H,13,14)

InChI Key

HICXXZOMOLMOII-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Acetamide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Alkylthiol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.32	ALOGPS
logP	-0.51	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	59 m³·mol⁻¹	ChemAxon
Polarizability	23.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	153.374	30932474
DeepCCS	[M-H]-	149.857	30932474
DeepCCS	[M-2H]-	187.319	30932474
DeepCCS	[M+Na]+	162.983	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid	CC(=O)NC(CS)(C=CCCO)C(O)=O	3248.2	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid	CC(=O)NC(CS)(C=CCCO)C(O)=O	1838.5	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid	CC(=O)NC(CS)(C=CCCO)C(O)=O	2033.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #1	CC(=O)NC(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	2141.4	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #1	CC(=O)NC(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	2132.9	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #1	CC(=O)NC(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C	2399.4	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #2	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2068.5	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #2	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2082.0	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #2	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2448.6	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #3	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2174.8	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #3	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2225.9	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #3	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2578.3	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #4	CC(=O)N(C(C=CCCO)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2133.7	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #4	CC(=O)N(C(C=CCCO)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2161.9	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TMS,isomer #4	CC(=O)N(C(C=CCCO)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2578.5	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,4TMS,isomer #1	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2158.5	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,4TMS,isomer #1	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2222.5	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,4TMS,isomer #1	CC(=O)N(C(C=CCCO[Si](C)(C)C)(CS[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2220.6	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #1	CC(=O)NC(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2834.3	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #1	CC(=O)NC(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2707.8	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #1	CC(=O)NC(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2660.3	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #2	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2746.4	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #2	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2688.7	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #2	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2740.0	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #3	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2885.5	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #3	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2811.3	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #3	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2808.5	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #4	CC(=O)N(C(C=CCCO)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2841.3	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #4	CC(=O)N(C(C=CCCO)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2754.5	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,3TBDMS,isomer #4	CC(=O)N(C(C=CCCO)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2778.6	Standard polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,4TBDMS,isomer #1	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3076.4	Semi standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,4TBDMS,isomer #1	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2947.4	Standard non polar	33892256
(2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid,4TBDMS,isomer #1	CC(=O)N(C(C=CCCO[Si](C)(C)C(C)(C)C)(CS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2619.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9810000000-b2638b8f2959a2cec64c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid (HMDB0257715)

MOL for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

3D MOL for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

3D SDF for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

3D-SDF for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

PDB for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

3D PDB for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

SMILES for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

INCHI for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

Structure for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

3D Structure for HMDB0257715 ((2R)-2-Acetamido-6-hydroxy-2-(sulfanylmethyl)hex-3-enoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra