Showing metabocard for S-Carboxymethyl-D-cysteine (MMDBc0030210)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:58:31 UTC
Update Date2022-08-31 17:40:42 UTC
Metabolite IDMMDBc0030210
Metabolite Identification
Common NameS-Carboxymethyl-D-cysteine
DescriptionS-carboxymethyl-D-cysteine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). S-carboxymethyl-D-cysteine is a product of the reaction of D-cysteine desulfhydraase with chloro-D-alanine, which is part of the chloro-alanine degradation process. D-Cysteine desulfhydrase also catalyzes the beta-replacement reaction of the chlorine of 3-chloro-D-alanine with thioglycolic acid to yield S-carboxymethyl-D-cysteine [PMID:3908101 ]
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x0000560be02682d8>

Structure #1
  Mrv0541 02241207352D          

 11 10  0  0  0  0            999 V2000
   -0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    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
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    0.0000 O   0  5  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
   -1.9520    1.9520    0.0000 O   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
  1  3  1  0  0  0  0
  1 11  1  0  0  0  0
  2  4  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
M  CHG  1   8  -1
M  END
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3D MOL for #<Metabolite:0x0000560be02682d8>

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3D SDF for #<Metabolite:0x0000560be02682d8>
Structure #1
  Mrv0541 02241207352D          

 11 10  0  0  0  0            999 V2000
   -0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    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
    1.6204    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204   -0.1105    0.0000 O   0  5  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
   -1.9520    1.9520    0.0000 O   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
  1  3  1  0  0  0  0
  1 11  1  0  0  0  0
  2  4  1  0  0  0  0
  2 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
M  CHG  1   8  -1
M  END
> <DATABASE_ID>
MMDBc0030210

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CSCC([O-])=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1

> <INCHI_KEY>
GBFLZEXEOZUWRN-UHFFFAOYSA-M

> <FORMULA>
C5H8NO4S

> <MOLECULAR_WEIGHT>
178.186

> <EXACT_MASS>
178.017403439

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.230940447992612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-amino-2-carboxyethyl)sulfanyl]acetate

> <ALOGPS_LOGP>
-2.87

> <JCHEM_LOGP>
-3.2974090328132886

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.052647186055013

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8428031112426706

> <JCHEM_PKA_STRONGEST_BASIC>
9.14390391869584

> <JCHEM_POLAR_SURFACE_AREA>
103.45

> <JCHEM_REFRACTIVITY>
49.943900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-amino-2-carboxyethyl)sulfanyl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x0000560be02682d8>
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PDB for #<Metabolite:0x0000560be02682d8>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.310  -0.206   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       4.358   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.025  -0.206   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      -4.977   1.334   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.644   3.644   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       0.357   1.334   0.000  0.00  0.00           S+0
CONECT    1    3   11                                                       
CONECT    2    4   11                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3    9   10                                                  
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
CONECT   11    1    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x0000560be02682d8>
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SMILES for #<Metabolite:0x0000560be02682d8>
NC(CSCC([O-])=O)C(O)=O
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INCHI for #<Metabolite:0x0000560be02682d8>
InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1
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Synonyms
ValueSource
2-[(2-Amino-2-carboxyethyl)sulfanyl]acetic acidGenerator
2-[(2-Amino-2-carboxyethyl)sulphanyl]acetateGenerator
2-[(2-Amino-2-carboxyethyl)sulphanyl]acetic acidGenerator
Molecular FormulaC5H8NO4S
Average Mass178.186
Monoisotopic Mass178.017403439
IUPAC Name2-[(2-amino-2-carboxyethyl)sulfanyl]acetate
Traditional Name2-[(2-amino-2-carboxyethyl)sulfanyl]acetate
CAS Registry NumberNot Available
SMILES
NC(CSCC([O-])=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO4S/c6-3(5(9)10)1-11-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1
InChI KeyGBFLZEXEOZUWRN-UHFFFAOYSA-M