MiMeDB: Showing metabocard for 2-(glutathione-S-yl)-hydroquinone (MMDBc0055201)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:46:06 UTC

Update Date

2022-08-12 20:09:16 UTC

Metabolite ID

MMDBc0055201

Metabolite Identification

Common Name

2-(glutathione-S-yl)-hydroquinone

Description

2-(glutathione-S-yl)-hydroquinone, also known as S-(2,5-dihydroxyphenyl)glutathione(1-), belongs to the class of organic compounds known as peptides. Peptides 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. Based on a literature review a small amount of articles have been published on 2-(glutathione-S-yl)-hydroquinone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221462D          

 30 30  0  0  1  0            999 V2000
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  7  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  4  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
  9 17  1  1  0  0  0
 18  6  1  4  0  0  0
 18 15  2  0  0  0  0
 10 19  1  1  0  0  0
 19 13  2  0  0  0  0
 20  8  1  0  0  0  0
 21 11  1  0  0  0  0
 13 22  1  4  0  0  0
 23 14  2  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26 16  2  0  0  0  0
 27 16  1  0  0  0  0
 28  7  1  0  0  0  0
 28 12  1  0  0  0  0
  9 29  1  1  0  0  0
 10 30  1  1  0  0  0
M  CHG  1  20  -1
M  END


  Mrv1652306172221462D          

 30 30  0  0  1  0            999 V2000
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  7  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  4  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
  9 17  1  1  0  0  0
 18  6  1  4  0  0  0
 18 15  2  0  0  0  0
 10 19  1  1  0  0  0
 19 13  2  0  0  0  0
 20  8  1  0  0  0  0
 21 11  1  0  0  0  0
 13 22  1  4  0  0  0
 23 14  2  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 26 16  2  0  0  0  0
 27 16  1  0  0  0  0
 28  7  1  0  0  0  0
 28 12  1  0  0  0  0
  9 29  1  1  0  0  0
 10 30  1  1  0  0  0
M  CHG  1  20  -1
M  END
> <DATABASE_ID>
MMDBc0055201

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1=C(O)C=CC([O-])=C1)C(O)=NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H21N3O8S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-28-12-5-8(20)1-3-11(12)21/h1,3,5,9-10,20-21H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/p-1/t9-,10-/m0/s1

> <INCHI_KEY>
PBSYQNUIZQXWAE-UWVGGRQHSA-M

> <FORMULA>
C16H20N3O8S

> <MOLECULAR_WEIGHT>
414.41

> <EXACT_MASS>
414.09765937

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.087088734043675

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-4-hydroxybenzen-1-olate

> <JCHEM_LOGP>
-2.202380879275887

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.0532452065585938

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7554700218984225

> <JCHEM_PKA_STRONGEST_BASIC>
9.229694165510654

> <JCHEM_POLAR_SURFACE_AREA>
209.08999999999997

> <JCHEM_REFRACTIVITY>
109.24660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}-4-hydroxybenzenolate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       9.336  11.550   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       4.001  10.010   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -2.667  13.860   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      12.003  10.010   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.669   7.700   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0      -0.000   9.240   0.000  0.00  0.00           S+0
HETATM   29  H   UNK     0       9.336   8.470   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.334   8.470   0.000  0.00  0.00           H+0
CONECT    1    3    8                                                       
CONECT    2    4    9                                                       
CONECT    3    1   11                                                       
CONECT    4    2   13                                                       
CONECT    5    8   12                                                       
CONECT    6   14   18                                                       
CONECT    7   10   28                                                       
CONECT    8    1    5   20                                                  
CONECT    9    2   16   17   29                                             
CONECT   10    7   15   19   30                                             
CONECT   11    3   12   21                                                  
CONECT   12    5   11   28                                                  
CONECT   13    4   19   22                                                  
CONECT   14    6   23   24                                                  
CONECT   15   10   18   25                                                  
CONECT   16    9   26   27                                                  
CONECT   17    9                                                            
CONECT   18    6   15                                                       
CONECT   19   10   13                                                       
CONECT   20    8                                                            
CONECT   21   11                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   16                                                            
CONECT   28    7   12                                                       
CONECT   29    9                                                            
CONECT   30   10                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

Synonyms

Value	Source
2-(Glutathion-S-yl)hydroquinone(1-)	ChEBI
S-(2,5-Dihydroxyphenyl)glutathione(1-)	ChEBI

Molecular Formula

C₁₆H₂₀N₃O₈S

Average Mass

414.41

Monoisotopic Mass

414.09765937

IUPAC Name

3-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-4-hydroxybenzen-1-olate

Traditional Name

3-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-(carboxymethyl-C-hydroxycarbonimidoyl)ethyl]sulfanyl}-4-hydroxybenzenolate

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1=C(O)C=CC([O-])=C1)C(O)=NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C16H21N3O8S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-28-12-5-8(20)1-3-11(12)21/h1,3,5,9-10,20-21H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/p-1/t9-,10-/m0/s1

InChI Key

PBSYQNUIZQXWAE-UWVGGRQHSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
L-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Aryl thioether
Thiophenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkylarylthioether
Phenoxide
Phenol
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Amino acid
Amino acid or derivatives
Sulfenyl compound
Thioether
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.2	ChemAxon
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.09 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	109.25 m³·mol⁻¹	ChemAxon
Polarizability	40.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Not Available

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

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	Proteobacteria	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

76962822

KEGG Compound ID

Not Available

BioCyc ID

CPD-19760

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124202377

PDB ID

Not Available

ChEBI ID

134616

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-(glutathione-S-yl)-hydroquinone (MMDBc0055201)

MOL for #<Metabolite:0x00007fdb7017a888>

3D MOL for #<Metabolite:0x00007fdb7017a888>

3D SDF for #<Metabolite:0x00007fdb7017a888>

3D-SDF for #<Metabolite:0x00007fdb7017a888>

PDB for #<Metabolite:0x00007fdb7017a888>

3D PDB for #<Metabolite:0x00007fdb7017a888>

SMILES for #<Metabolite:0x00007fdb7017a888>

INCHI for #<Metabolite:0x00007fdb7017a888>

Structure for #<Metabolite:0x00007fdb7017a888>

3D Structure for #<Metabolite:0x00007fdb7017a888>