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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:04 UTC
Update Date2019-07-23 07:14:14 UTC
HMDB IDHMDB0060391
Secondary Accession Numbers
  • HMDB60391
Metabolite Identification
Common Name4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene
Description4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene 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. 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene is a very strong basic compound (based on its pKa). 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene exists in all living organisms, ranging from bacteria to humans. 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
Data?1563866054
SynonymsNot Available
Chemical FormulaC30H29N3O7S
Average Molecular Weight575.632
Monoisotopic Molecular Weight575.172620987
IUPAC Name(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({11-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional Name(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-({11-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=CC3=CC=CC=C3C3=C2C2=C(C=CC=C2C1([H])O)C=C3)C(O)=NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C30H29N3O7S/c31-21(30(39)40)10-11-23(34)33-22(29(38)32-13-24(35)36)14-41-28-20-12-16-4-1-2-6-17(16)18-9-8-15-5-3-7-19(27(28)37)25(15)26(18)20/h1-9,12,21-22,27-28,37H,10-11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,27?,28?/m0/s1
InChI KeyPZXCOGFLSNREMF-SUZCJKPRSA-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Chrysene
  • Glutamine or derivatives
  • Phenanthrene
  • 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
  • Naphthalene
  • L-alpha-amino acid
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Dialkylthioether
  • Carboxylic acid
  • Sulfenyl compound
  • Thioether
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organosulfur compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP0.19ALOGPS
logP0.68ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)2.07ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.03 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity153.14 m³·mol⁻¹ChemAxon
Polarizability59.66 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3090070000-318cd5522f8b31ca9e5cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2090024000-028df145f70e0dd65b29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0adj-2011390000-7a7dbf308ba61fa538f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9103720000-1eef252466caae626959Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9142100000-aa9f26588448cdcc954cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kn9-0133090000-45cda9ad0c81d7f90fd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0196010000-141a30f61669cde8948aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-2942000000-afdbd3b8e287537675d8Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10128363
KEGG Compound IDC14855
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11954068
PDB IDNot Available
ChEBI ID34374
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM2
Uniprot ID:
P28161
Molecular weight:
25744.395
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM1
Uniprot ID:
P09488
Molecular weight:
25711.555
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in protein disulfide oxidoreductase activity
Specific function:
Significant glutathione conjugating activity is found only with the model substrate, 1-chloro-2,4-dinitrobenzene (CDNB).
Gene Name:
GSTK1
Uniprot ID:
Q9Y2Q3
Molecular weight:
31565.605
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Also functions as a glutathione peroxidase.
Gene Name:
MGST3
Uniprot ID:
O14880
Molecular weight:
16516.185
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the testis and brain blood barriers.
Gene Name:
GSTM3
Uniprot ID:
P21266
Molecular weight:
26559.32
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA1
Uniprot ID:
P08263
Molecular weight:
25630.785
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
Gene Name:
MGST1
Uniprot ID:
P10620
Molecular weight:
17598.45
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name:
GSTM4
Uniprot ID:
Q03013
Molecular weight:
25561.095
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTM5
Uniprot ID:
P46439
Molecular weight:
25674.455
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails
General function:
Involved in enzyme activator activity
Specific function:
Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
Gene Name:
MGST2
Uniprot ID:
Q99735
Molecular weight:
16620.4
Reactions
Benzo[a]pyrene-4,5-oxide + Glutathione → 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrenedetails

Only showing the first 10 proteins. There are 19 proteins in total.