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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:19:33 UTC

Update Date

2022-09-22 18:35:12 UTC

HMDB ID

HMDB0060011

Secondary Accession Numbers

HMDB60011

Metabolite Identification

Common Name

N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine

Description

N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 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. N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine is an extremely weak basic (essentially neutral) compound (based on its pKa). These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Structure

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

HMDB0060011
     RDKit          3D
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.5487    1.1875    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -0.0054    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706   -0.2160   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6757   -0.6828    0.4876 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.9307   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3225   -0.6691   -1.7873 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -1.5109    0.7301 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -1.7226   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.4768   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4625    0.4347    0.4640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    0.6311    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1348    1.5529    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7101   -0.0094    0.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074    0.1031   -1.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.3098   -1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.6597   -3.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869    2.0047    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    1.4167    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614   -0.8201    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    0.7163   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235   -0.9768   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -0.8474    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -2.3411   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -2.3077    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -0.8831   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    0.9920    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059    2.0549    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    2.2841    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6042    0.9437    2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375   -0.5720   -3.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 16 30  1  0
M  END


  Mrv0541 04091314192D          

 16 15  0  0  0  0            999 V2000
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    4.0954    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060011

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC(CSC(=S)NCC=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N2O3S2/c1-3-4-10-9(15)16-5-7(8(13)14)11-6(2)12/h3,7H,1,4-5H2,2H3,(H,10,15)(H,11,12)(H,13,14)

> <INCHI_KEY>
DJFUZUUKZXAXBZ-UHFFFAOYSA-N

> <FORMULA>
C9H14N2O3S2

> <MOLECULAR_WEIGHT>
262.349

> <EXACT_MASS>
262.044583704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.42731325871623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetamido-3-{[(prop-2-en-1-yl)carbamothioyl]sulfanyl}propanoic acid

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
0.6405447543333329

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.389505668622116

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.061564148656337

> <JCHEM_PKA_STRONGEST_BASIC>
-1.495268143985451

> <JCHEM_POLAR_SURFACE_AREA>
78.43

> <JCHEM_REFRACTIVITY>
67.86219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-3-{[(prop-2-en-1-yl)carbamothioyl]sulfanyl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060011
     RDKit          3D
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.5487    1.1875    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -0.0054    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706   -0.2160   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6757   -0.6828    0.4876 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.9307   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3225   -0.6691   -1.7873 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -1.5109    0.7301 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -1.7226   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.4768   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4625    0.4347    0.4640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    0.6311    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1348    1.5529    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7101   -0.0094    0.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074    0.1031   -1.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.3098   -1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.6597   -3.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869    2.0047    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    1.4167    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614   -0.8201    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    0.7163   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235   -0.9768   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -0.8474    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -2.3411   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -2.3077    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -0.8831   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    0.9920    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059    2.0549    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    2.2841    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6042    0.9437    2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375   -0.5720   -3.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 09-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-13         0                                  
HETATM    1  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      10.574   6.105   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      14.575   5.335   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0      15.908   7.645   0.000  0.00  0.00           S+0
HETATM   10  N   UNK     0      17.242   5.335   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.907   3.795   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.241   3.025   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.574   3.025   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   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0060011
HETATM    1  C1  UNL     1       5.549   1.187   0.537  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.004  -0.005   0.491  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.771  -0.216  -0.282  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.676  -0.683   0.488  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.411  -0.931  -0.179  1.00  0.00           C  
HETATM    6  S1  UNL     1       1.323  -0.669  -1.787  1.00  0.00           S  
HETATM    7  S2  UNL     1       0.027  -1.511   0.730  1.00  0.00           S  
HETATM    8  C5  UNL     1      -1.491  -1.723  -0.128  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.195  -0.477  -0.611  1.00  0.00           C  
HETATM   10  N2  UNL     1      -2.463   0.435   0.464  1.00  0.00           N  
HETATM   11  C7  UNL     1      -3.773   0.631   0.942  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.135   1.553   2.047  1.00  0.00           C  
HETATM   13  O1  UNL     1      -4.710  -0.009   0.408  1.00  0.00           O  
HETATM   14  C9  UNL     1      -1.707   0.103  -1.853  1.00  0.00           C  
HETATM   15  O2  UNL     1      -1.373   1.310  -1.952  1.00  0.00           O  
HETATM   16  O3  UNL     1      -1.586  -0.660  -3.036  1.00  0.00           O  
HETATM   17  H1  UNL     1       5.087   2.005   0.008  1.00  0.00           H  
HETATM   18  H2  UNL     1       6.465   1.417   1.089  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.461  -0.820   1.018  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.469   0.716  -0.807  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.023  -0.977  -1.079  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.758  -0.847   1.499  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.341  -2.341  -1.051  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.262  -2.308   0.466  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.243  -0.883  -0.894  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.702   0.992   0.940  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.206   2.055   2.374  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.894   2.284   1.709  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.604   0.944   2.871  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.337  -0.572  -3.700  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5   22
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   14   25
CONECT   10   11   26
CONECT   11   12   13   13
CONECT   12   27   28   29
CONECT   14   15   15   16
CONECT   16   30
END

HMDB0060011
     RDKit          3D
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine
 30 29  0  0  0  0  0  0  0  0999 V2000
    5.5487    1.1875    0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -0.0054    0.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706   -0.2160   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6757   -0.6828    0.4876 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106   -0.9307   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3225   -0.6691   -1.7873 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0268   -1.5109    0.7301 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -1.7226   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.4768   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4625    0.4347    0.4640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727    0.6311    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1348    1.5529    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7101   -0.0094    0.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074    0.1031   -1.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3725    1.3098   -1.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.6597   -3.0361 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0869    2.0047    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    1.4167    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614   -0.8201    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    0.7163   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235   -0.9768   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7577   -0.8474    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -2.3411   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618   -2.3077    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -0.8831   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    0.9920    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059    2.0549    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    2.2841    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6042    0.9437    2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375   -0.5720   -3.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  9 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxyethylidene)amino]-3-{[(prop-2-en-1-yl)thio(carbonoimidyl)]sulfanyl}propanoate	Generator
2-[(1-Hydroxyethylidene)amino]-3-{[(prop-2-en-1-yl)thio(carbonoimidyl)]sulphanyl}propanoate	Generator
2-[(1-Hydroxyethylidene)amino]-3-{[(prop-2-en-1-yl)thio(carbonoimidyl)]sulphanyl}propanoic acid	Generator
Ac-atc-cys	MeSH
N-Acetyl-S-(N-allylthiocarbamoyl)-L-cysteine	MeSH
N-Acetyl-S-(N-allylthiocarbamoyl)cysteine	MeSH

Chemical Formula

C₉H₁₄N₂O₃S₂

Average Molecular Weight

262.349

Monoisotopic Molecular Weight

262.044583704

IUPAC Name

2-acetamido-3-{[(prop-2-en-1-yl)carbamothioyl]sulfanyl}propanoic acid

Traditional Name

2-acetamido-3-{[(prop-2-en-1-yl)carbamothioyl]sulfanyl}propanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC(CSC(=S)NCC=C)C(O)=O

InChI Identifier

InChI=1S/C9H14N2O3S2/c1-3-4-10-9(15)16-5-7(8(13)14)11-6(2)12/h3,7H,1,4-5H2,2H3,(H,10,15)(H,11,12)(H,13,14)

InChI Key

DJFUZUUKZXAXBZ-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
Cysteine or derivatives
Acetamide
Dithiocarbamic acid ester
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl compound
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 8000299)

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
Water Solubility	0.093 g/L	ALOGPS
logP	0.54	ALOGPS
logP	0.64	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.86 m³·mol⁻¹	ChemAxon
Polarizability	26.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	160.184	31661259
DarkChem	[M-H]-	151.702	31661259
DeepCCS	[M+H]+	152.216	30932474
DeepCCS	[M-H]-	149.275	30932474
DeepCCS	[M-2H]-	185.929	30932474
DeepCCS	[M+Na]+	161.517	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	153.1	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.7	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	3.4 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8436 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1739.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	314.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	387.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	585.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	834.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	357.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1430.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	288.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	560.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	213.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	92.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine	CC(=O)NC(CSC(=S)NCC=C)C(O)=O	3869.2	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine	CC(=O)NC(CSC(=S)NCC=C)C(O)=O	2151.2	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine	CC(=O)NC(CSC(=S)NCC=C)C(O)=O	2494.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,1TMS,isomer #1	C=CCNC(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C	2253.1	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,1TMS,isomer #2	C=CCNC(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C	2271.3	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,1TMS,isomer #3	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O)[Si](C)(C)C	2307.7	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #1	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2302.2	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #1	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2204.9	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #1	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3145.5	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #2	C=CCNC(=S)SCC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	2256.5	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #2	C=CCNC(=S)SCC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	2131.8	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #2	C=CCNC(=S)SCC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C	3389.4	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #3	C=CCN(C(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2299.9	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #3	C=CCN(C(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2270.5	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TMS,isomer #3	C=CCN(C(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	3214.3	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,3TMS,isomer #1	C=CCN(C(=S)SCC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2297.4	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,3TMS,isomer #1	C=CCN(C(=S)SCC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2265.6	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,3TMS,isomer #1	C=CCN(C(=S)SCC(C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C	2804.5	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,1TBDMS,isomer #1	C=CCNC(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C	2487.6	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,1TBDMS,isomer #2	C=CCNC(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C	2483.0	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,1TBDMS,isomer #3	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O)[Si](C)(C)C(C)(C)C	2531.6	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #1	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2750.3	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #1	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2600.1	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #1	C=CCN(C(=S)SCC(NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3197.0	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #2	C=CCNC(=S)SCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	2673.2	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #2	C=CCNC(=S)SCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	2556.2	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #2	C=CCNC(=S)SCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C	3387.8	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #3	C=CCN(C(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2778.7	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #3	C=CCN(C(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2623.8	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,2TBDMS,isomer #3	C=CCN(C(=S)SCC(C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3247.9	Standard polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,3TBDMS,isomer #1	C=CCN(C(=S)SCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2964.3	Semi standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,3TBDMS,isomer #1	C=CCN(C(=S)SCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2845.2	Standard non polar	33892256
N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine,3TBDMS,isomer #1	C=CCN(C(=S)SCC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3046.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9320000000-bf0cb6451be37c388a3a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine GC-MS (1 TMS) - 70eV, Positive	splash10-00r6-9211000000-ee1133670216bdd1ba7b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 10V, Positive-QTOF	splash10-03di-1930000000-f0d2b8ac546b4aefd5f7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 20V, Positive-QTOF	splash10-01ox-7950000000-c742c3f56c18ed0f7dca	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 40V, Positive-QTOF	splash10-0006-9300000000-095c894b0184ae1d3b27	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 10V, Negative-QTOF	splash10-03dj-4290000000-ef94e8d3017f0a64553d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 20V, Negative-QTOF	splash10-0a5a-9620000000-01bfc8a015c9f3d46008	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 40V, Negative-QTOF	splash10-0a59-9100000000-cfbc613da08d452851ed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 10V, Positive-QTOF	splash10-0ik9-0690000000-0aca6a357b4496175947	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 20V, Positive-QTOF	splash10-0uec-6920000000-89dd25a546338d835b2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 40V, Positive-QTOF	splash10-0pe9-7900000000-7b950def196e3842d046	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 10V, Negative-QTOF	splash10-03xr-0910000000-d1080bfe03e9d1b63858	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 20V, Negative-QTOF	splash10-001j-9100000000-06010de5c4989212e71b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine 40V, Negative-QTOF	splash10-001l-9100000000-64a42e014c3450ae8f01	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	8000299	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24390407	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Maj-Britt Sc...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

5744015

PDB ID

Not Available

ChEBI ID

89611

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

Jiao D, Ho CT, Foiles P, Chung FL: Identification and quantification of the N-acetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol Biomarkers Prev. 1994 Sep;3(6):487-92. [PubMed:8000299 ]

Showing metabocard for N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine (HMDB0060011)

MOL for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

3D MOL for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

3D SDF for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

3D-SDF for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

PDB for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

3D PDB for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

SMILES for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

INCHI for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

Structure for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

3D Structure for HMDB0060011 (N-acetyl-S-(N-allylthiocarbamoyl)-L-cysteine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra