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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:20:51 UTC
Update Date2021-09-14 15:37:23 UTC
HMDB IDHMDB0060438
Secondary Accession Numbers
  • HMDB60438
Metabolite Identification
Common NameBenzo[a]pyrene-7,8-diol
DescriptionBenzo[a]pyrene-7,8-diol, also known as BP-7,8 diol, belongs to the class of organic compounds known as pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system. Benzo[a]pyrene-7,8-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzo[a]pyrene-7,8-diol exists in all living organisms, ranging from bacteria to humans. These are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.
Structure
Data?1563866060
Synonyms
ValueSource
Benzo[a]pyrene-7,8-dihydrodiolKegg
7,8-Dihydroxy-7,8-dihydrobenzo(a)pyreneHMDB
Benzo(a)pyrene 7,8-dihydrodiol, (7R-trans)-isomerHMDB
Benzopyrene-7,8-dihydrodiolHMDB
7,8-Dihydro-7,8-dihydroxybenzopyreneHMDB
7,8-Dihydrobenzo(a)pyrene-7,8-diolHMDB
BP-7,8 DiolHMDB
Benzo(a)pyrene 7,8-dihydrodiol, (cis)-isomerHMDB
trans-Benzopyrene 7,8-dihydrodiolHMDB
7,8-Dihydro 7,8-dihydroxybenzo(a)pyreneHMDB
Benzo(a)pyrene 7,8-dihydrodiol, (trans)-(+-)-isomerHMDB
Benzo(a)pyrene 7,8-dihydrodiol, (trans)-isomerHMDB
Benzo(a)pyrene 7,8-dihydrodiol, (7S-trans)-isomerHMDB
trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyreneHMDB
Benzo(a)pyrene 7,8-dihydrodiolMeSH
Chemical FormulaC20H14O2
Average Molecular Weight286.324
Monoisotopic Molecular Weight286.099379692
IUPAC Namepentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol
Traditional Namebenzo(a)pyrene 7,8-diol
CAS Registry NumberNot Available
SMILES
OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O
InChI Identifier
InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H
InChI KeyYDXRLMMGARHIIC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassNot Available
Direct ParentPyrenes
Alternative Parents
Substituents
  • Pyrene
  • Phenanthrol
  • Phenanthrene
  • Naphthalene
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP10(3.61) g/LALOGPS
logP10(3.31) g/LChemAxon
logS10(-5.3) g/LALOGPS
pKa (Strongest Acidic)13.15ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.04 m³·mol⁻¹ChemAxon
Polarizability31.45 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.31931661259
DarkChem[M-H]-164.8331661259
DeepCCS[M+H]+177.11830932474
DeepCCS[M-H]-174.7630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyrene-7,8-diolOC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O4298.7Standard polar33892256
Benzo[a]pyrene-7,8-diolOC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O2988.4Standard non polar33892256
Benzo[a]pyrene-7,8-diolOC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O3274.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyrene-7,8-diol,1TMS,isomer #1C[Si](C)(C)OC1C=CC2=C(C=C3C=CC4=CC=CC5=CC=C2C3=C45)C1O3146.4Semi standard non polar33892256
Benzo[a]pyrene-7,8-diol,1TMS,isomer #2C[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C=CC1O)C3=C453101.5Semi standard non polar33892256
Benzo[a]pyrene-7,8-diol,2TMS,isomer #1C[Si](C)(C)OC1C=CC2=C(C=C3C=CC4=CC=CC5=CC=C2C3=C45)C1O[Si](C)(C)C3076.8Semi standard non polar33892256
Benzo[a]pyrene-7,8-diol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C=CC2=C(C=C3C=CC4=CC=CC5=CC=C2C3=C45)C1O3366.3Semi standard non polar33892256
Benzo[a]pyrene-7,8-diol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C=CC1O)C3=C453310.2Semi standard non polar33892256
Benzo[a]pyrene-7,8-diol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C=CC2=C(C=C3C=CC4=CC=CC5=CC=C2C3=C45)C1O[Si](C)(C)C(C)(C)C3508.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-0090000000-d0f9942584aaf480d9992017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0103-8009100000-fe801e46e710eea32e4f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-diol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-diol 10V, Positive-QTOFsplash10-000i-0090000000-e746f506858cf64c915a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-diol 20V, Positive-QTOFsplash10-0k9i-1090000000-fcf1f10a8966181578922015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-diol 40V, Positive-QTOFsplash10-0gb9-1290000000-d88f3784dd0a513870f42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-diol 10V, Negative-QTOFsplash10-000i-0090000000-7c6172f7110a47ae0a1a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-diol 20V, Negative-QTOFsplash10-000i-0090000000-40d4296cbb4974e7d7c72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-diol 40V, Negative-QTOFsplash10-0a70-1090000000-35194879c01560da4ee12015-09-15Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDNot Available
KEGG Compound IDC14852
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25892
PDB IDNot Available
ChEBI ID34562
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 20 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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails
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-7,8-diol + Glutathione → 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Waterdetails

Only showing the first 10 proteins. There are 20 proteins in total.