MiMeDB: Showing metabocard for S-(2-Chloroacetyl)glutathione (MMDBc0030090)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:53:32 UTC

Update Date

2024-04-30 19:44:35 UTC

Metabolite ID

MMDBc0030090

Metabolite Identification

Common Name

S-(2-Chloroacetyl)glutathione

Description

S-(2-chloroacetyl)glutathione is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Structure

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


  Mrv0541 08131209322D          

 26 25  0  0  0  0            999 V2000
    6.9533    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    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
    4.8099   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.7605    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
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -2.5855    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
    3.3809   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  3  1  0  0  0  0
  6 14  1  1  0  0  0
 15  4  1  4  0  0  0
 15 11  2  0  0  0  0
  7 16  1  1  0  0  0
 16  8  2  0  0  0  0
  8 17  1  4  0  0  0
 18  9  2  0  0  0  0
 19  9  1  0  0  0  0
 20 10  2  0  0  0  0
 21 11  1  0  0  0  0
 22 12  2  0  0  0  0
 23 12  1  0  0  0  0
 24  5  1  0  0  0  0
 24 10  1  0  0  0  0
  6 25  1  1  0  0  0
  7 26  1  1  0  0  0
M  END

HMDB0060505
     RDKit          3D
S-(2-Chloroacetyl)glutathione
 42 41  0  0  0  0  0  0  0  0999 V2000
    4.7150    0.1755   -1.9632 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952    0.9410   -0.7788 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8938    0.9941   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -0.4276   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -0.4310   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2494   -1.6503   -0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.6319   -0.0987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    0.6792    0.0813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9283    1.1163   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    1.0997   -0.6776 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9993    2.4124    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9821    2.3316    1.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    3.6077    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341    4.2033   -1.0792 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -0.6422    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -1.2999    1.6230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.1958   -0.2990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -2.4333    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.2639   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4721   -2.9702   -2.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2604   -4.4796   -0.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9964    0.3483    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891    0.9110    1.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7889   -0.8110    0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5984    0.5216   -2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8513   -0.8426   -1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7947    1.9821   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439    1.4943   -1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    1.5357    0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6995   -1.0249   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.8366    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6825   -2.5443   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.3603    0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    2.0519   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912    0.2622   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    4.4499    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    3.4859    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -0.7001    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -3.0118    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1779   -2.2196    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -5.1319   -0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8071   -0.6792    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 24 42  1  0
M  END


  Mrv0541 08131209322D          

 26 25  0  0  0  0            999 V2000
    6.9533    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    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
    4.8099   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.7605    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
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -2.5855    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
    3.3809   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  3  1  0  0  0  0
  6 14  1  1  0  0  0
 15  4  1  4  0  0  0
 15 11  2  0  0  0  0
  7 16  1  1  0  0  0
 16  8  2  0  0  0  0
  8 17  1  4  0  0  0
 18  9  2  0  0  0  0
 19  9  1  0  0  0  0
 20 10  2  0  0  0  0
 21 11  1  0  0  0  0
 22 12  2  0  0  0  0
 23 12  1  0  0  0  0
 24  5  1  0  0  0  0
 24 10  1  0  0  0  0
  6 25  1  1  0  0  0
  7 26  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030090

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC(O)=N[C@@]([H])(CSC(=O)CCl)C(O)=NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18ClN3O7S/c13-3-10(20)24-5-7(11(21)15-4-9(18)19)16-8(17)2-1-6(14)12(22)23/h6-7H,1-5,14H2,(H,15,21)(H,16,17)(H,18,19)(H,22,23)/t6-,7-/m0/s1

> <INCHI_KEY>
QJDRMMRBPVHMAD-BQBZGAKWSA-N

> <FORMULA>
C12H18ClN3O7S

> <MOLECULAR_WEIGHT>
383.805

> <EXACT_MASS>
383.055398342

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
35.591051216419956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-chloroacetyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <ALOGPS_LOGP>
-2.21

> <JCHEM_LOGP>
-2.881631024486895

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.6309459773955064

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7844085108860162

> <JCHEM_PKA_STRONGEST_BASIC>
9.537332726334014

> <JCHEM_POLAR_SURFACE_AREA>
182.86999999999998

> <JCHEM_REFRACTIVITY>
84.3793

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Clch2COSG

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060505
     RDKit          3D
S-(2-Chloroacetyl)glutathione
 42 41  0  0  0  0  0  0  0  0999 V2000
    4.7150    0.1755   -1.9632 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952    0.9410   -0.7788 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8938    0.9941   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -0.4276   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -0.4310   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2494   -1.6503   -0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.6319   -0.0987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    0.6792    0.0813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9283    1.1163   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    1.0997   -0.6776 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9993    2.4124    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9821    2.3316    1.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    3.6077    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341    4.2033   -1.0792 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -0.6422    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -1.2999    1.6230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.1958   -0.2990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -2.4333    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.2639   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4721   -2.9702   -2.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2604   -4.4796   -0.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9964    0.3483    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891    0.9110    1.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7889   -0.8110    0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5984    0.5216   -2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8513   -0.8426   -1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7947    1.9821   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439    1.4943   -1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    1.5357    0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6995   -1.0249   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.8366    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6825   -2.5443   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.3603    0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    2.0519   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912    0.2622   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    4.4499    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    3.4859    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -0.7001    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -3.0118    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1779   -2.2196    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -5.1319   -0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8071   -0.6792    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 24 42  1  0
M  END

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3   10   13                                                       
CONECT    4    9   15                                                       
CONECT    5    7   24                                                       
CONECT    6    1   12   14   25                                             
CONECT    7    5   11   16   26                                             
CONECT    8    2   16   17                                                  
CONECT    9    4   18   19                                                  
CONECT   10    3   20   24                                                  
CONECT   11    7   15   21                                                  
CONECT   12    6   22   23                                                  
CONECT   13    3                                                            
CONECT   14    6                                                            
CONECT   15    4   11                                                       
CONECT   16    7    8                                                       
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   12                                                            
CONECT   24    5   10                                                       
CONECT   25    6                                                            
CONECT   26    7                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0060505
HETATM    1  N1  UNL     1       4.715   0.175  -1.963  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.395   0.941  -0.779  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.894   0.994  -0.605  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.387  -0.428  -0.474  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.896  -0.431  -0.288  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.249  -1.650  -0.327  1.00  0.00           O  
HETATM    7  N2  UNL     1       0.243   0.632  -0.099  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.153   0.679   0.081  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.928   1.116  -1.180  1.00  0.00           C  
HETATM   10  S1  UNL     1      -3.654   1.100  -0.678  1.00  0.00           S  
HETATM   11  C7  UNL     1      -3.999   2.412   0.440  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.982   2.332   1.176  1.00  0.00           O  
HETATM   13  C8  UNL     1      -3.153   3.608   0.540  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -2.634   4.203  -1.079  1.00  0.00          CL  
HETATM   15  C9  UNL     1      -1.791  -0.642   0.439  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.418  -1.300   1.623  1.00  0.00           O  
HETATM   17  N3  UNL     1      -2.667  -1.196  -0.299  1.00  0.00           N  
HETATM   18  C10 UNL     1      -3.256  -2.433   0.051  1.00  0.00           C  
HETATM   19  C11 UNL     1      -3.646  -3.264  -1.112  1.00  0.00           C  
HETATM   20  O4  UNL     1      -3.472  -2.970  -2.300  1.00  0.00           O  
HETATM   21  O5  UNL     1      -4.260  -4.480  -0.836  1.00  0.00           O  
HETATM   22  C12 UNL     1       4.996   0.348   0.435  1.00  0.00           C  
HETATM   23  O6  UNL     1       4.789   0.911   1.549  1.00  0.00           O  
HETATM   24  O7  UNL     1       5.789  -0.811   0.409  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.598   0.522  -2.409  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.851  -0.843  -1.706  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.795   1.982  -0.868  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.444   1.494  -1.467  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.663   1.536   0.347  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.699  -1.025  -1.339  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.846  -0.837   0.431  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.682  -2.544  -0.248  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.429   1.360   0.891  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.570   2.052  -1.590  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.791   0.262  -1.895  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.773   4.450   0.953  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.256   3.486   1.170  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.364  -0.700   2.446  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.520  -3.012   0.649  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.178  -2.220   0.652  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.846  -5.132  -0.184  1.00  0.00           H  
HETATM   42  H18 UNL     1       6.807  -0.679   0.437  1.00  0.00           H  
CONECT    1    2   25   26
CONECT    2    3   22   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6    7    7
CONECT    6   32
CONECT    7    8
CONECT    8    9   15   33
CONECT    9   10   34   35
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   36   37
CONECT   15   16   17   17
CONECT   16   38
CONECT   17   18
CONECT   18   19   39   40
CONECT   19   20   20   21
CONECT   21   41
CONECT   22   23   23   24
CONECT   24   42
END

HMDB0060505
     RDKit          3D
S-(2-Chloroacetyl)glutathione
 42 41  0  0  0  0  0  0  0  0999 V2000
    4.7150    0.1755   -1.9632 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952    0.9410   -0.7788 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8938    0.9941   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3866   -0.4276   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -0.4310   -0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2494   -1.6503   -0.3269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432    0.6319   -0.0987 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    0.6792    0.0813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9283    1.1163   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6543    1.0997   -0.6776 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9993    2.4124    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9821    2.3316    1.1762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1529    3.6077    0.5395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341    4.2033   -1.0792 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7907   -0.6422    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -1.2999    1.6230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.1958   -0.2990 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -2.4333    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -3.2639   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4721   -2.9702   -2.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2604   -4.4796   -0.8363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9964    0.3483    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7891    0.9110    1.5488 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7889   -0.8110    0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5984    0.5216   -2.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8513   -0.8426   -1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7947    1.9821   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4439    1.4943   -1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    1.5357    0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6995   -1.0249   -1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -0.8366    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6825   -2.5443   -0.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290    1.3603    0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    2.0519   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912    0.2622   -1.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7731    4.4499    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    3.4859    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -0.7001    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -3.0118    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1779   -2.2196    0.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8463   -5.1319   -0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8071   -0.6792    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
  8 15  1  0
 15 16  1  0
 15 17  2  3
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  2 22  1  0
 22 23  2  0
 22 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  8 33  1  1
  9 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 21 41  1  0
 24 42  1  0
M  END

Synonyms

Value	Source
CLCH2COSG	HMDB
2-Chloroacetylglutathione	HMDB

Molecular Formula

C₁₂H₁₈ClN₃O₇S

Average Mass

383.805

Monoisotopic Mass

383.055398342

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-[(2-chloroacetyl)sulfanyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional Name

Clch2COSG

CAS Registry Number

113668-38-5

SMILES

[H][C@](N)(CCC(O)=N[C@@]([H])(CSC(=O)CCl)C(O)=NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H18ClN3O7S/c13-3-10(20)24-5-7(11(21)15-4-9(18)19)16-8(17)2-1-6(14)12(22)23/h6-7H,1-5,14H2,(H,15,21)(H,16,17)(H,18,19)(H,22,23)/t6-,7-/m0/s1

InChI Key

QJDRMMRBPVHMAD-BQBZGAKWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
S-acylglutathione
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Halogenated fatty acid
N-acyl-amine
Fatty acyl
Fatty acid
Fatty amide
Dicarboxylic acid or derivatives
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Thiocarboxylic acid ester
Carbothioic s-ester
Carboxamide group
Sulfenyl compound
Carboxylic acid
Thiocarboxylic acid or derivatives
Organohalogen compound
Primary aliphatic amine
Organooxygen compound
Organosulfur compound
Primary amine
Alkyl halide
Alkyl chloride
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organochloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

peptide (CHEBI:34959 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-2.9	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.87 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	84.38 m³·mol⁻¹	ChemAxon
Polarizability	35.59 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192428	Glutathione S-transferase Mu 2	Enzyme	P28161	Homo sapiens
MMDBp0192431	Glutathione S-transferase Mu 1	Enzyme	P09488	Homo sapiens
MMDBp0192433	Glutathione S-transferase kappa 1	Enzyme	Q9Y2Q3	Homo sapiens
MMDBp0192434	Microsomal glutathione S-transferase 3	Enzyme	O14880	Homo sapiens
MMDBp0192435	Glutathione S-transferase Mu 3	Enzyme	P21266	Homo sapiens
MMDBp0192436	Glutathione S-transferase A1	Enzyme	P08263	Homo sapiens
MMDBp0192438	Microsomal glutathione S-transferase 1	Enzyme	P10620	Homo sapiens
MMDBp0192439	Glutathione S-transferase Mu 4	Enzyme	Q03013	Homo sapiens
MMDBp0192440	Glutathione S-transferase Mu 5	Enzyme	P46439	Homo sapiens
MMDBp0192441	Microsomal glutathione S-transferase 2	Enzyme	Q99735	Homo sapiens
MMDBp0192442	Glutathione S-transferase omega-1	Enzyme	P78417	Homo sapiens
MMDBp0192443	Glutathione S-transferase A5	Enzyme	Q7RTV2	Homo sapiens
MMDBp0192444	Glutathione S-transferase A2	Enzyme	P09210	Homo sapiens
MMDBp0192446	Glutathione S-transferase A3	Enzyme	Q16772	Homo sapiens
MMDBp0192447	Glutathione S-transferase A4	Enzyme	O15217	Homo sapiens
MMDBp0192451	Glutathione S-transferase omega-2	Enzyme	Q9H4Y5	Homo sapiens
MMDBp0192452	Glutathione S-transferase theta-1	Unknown	P30711	Homo sapiens
MMDBp0192454	Glutathione S-transferase P	Enzyme	P09211	Homo sapiens
MMDBp0196825	Glutathione S-transferase theta-2B	Unknown	P0CG30

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0060505

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

143757

KEGG Compound ID

C14864

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163913

PDB ID

Not Available

ChEBI ID

34959

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Showing metabocard for S-(2-Chloroacetyl)glutathione (MMDBc0030090)

MOL for #<Metabolite:0x00007f92509f0fa8>

3D MOL for #<Metabolite:0x00007f92509f0fa8>

3D SDF for #<Metabolite:0x00007f92509f0fa8>

3D-SDF for #<Metabolite:0x00007f92509f0fa8>

PDB for #<Metabolite:0x00007f92509f0fa8>

3D PDB for #<Metabolite:0x00007f92509f0fa8>

SMILES for #<Metabolite:0x00007f92509f0fa8>

INCHI for #<Metabolite:0x00007f92509f0fa8>

Structure for #<Metabolite:0x00007f92509f0fa8>

3D Structure for #<Metabolite:0x00007f92509f0fa8>