Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 01:52:11 UTC
Update Date2021-09-14 15:17:01 UTC
HMDB IDHMDB0062470
Secondary Accession Numbers
  • HMDB62470
Metabolite Identification
Common NameBenzo[a]pyrene-7,8-dihydrodiol-9,10-oxide
DescriptionBenzo[a]pyrene-7,8-dihydrodiol-9,10-oxide, also known as BPDE or benzo(a)Pyrene diol epoxide, is classified as a member of the 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-dihydrodiol-9,10-oxide is considered to be practically insoluble (in water) and relatively neutral. It is a carcinogenic metabolite of benzo[a]pyrene (BaP) which forms adducts with DNA and proteins and is hydrolysed to BPDE tetrols. It is used as a marker for BaP exposure (a surrogate marker for PAHs).
Structure
Data?1563866316
Synonyms
ValueSource
7,8-Dihydro-7,8-dihydroxybenzo[a]pyrene 9,10-oxideChEBI
Benzo(a)pyrene diol epoxideChEBI
Benzo(a)pyrene diolepoxide IChEBI
BP 7,8-Diol-9,10-epoxide 2ChEBI
BPDEChEBI
7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyreneHMDB
Anti bapdeHMDB
Benzo(a)pyrene 7,8-dihydrodiol 9,10-epoxideHMDB
Benzo(a)pyrene-7,8-diol 9,10-epoxideHMDB
7,8-BaP-9,10-diol epoxideHMDB
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxideHMDB
Anti-bapdeHMDB
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxideChEBI
Chemical FormulaC20H14O3
Average Molecular Weight302.3234
Monoisotopic Molecular Weight302.094294314
IUPAC Name4-oxahexacyclo[11.6.2.0²,⁸.0³,⁵.0¹⁰,²⁰.0¹⁷,²¹]henicosa-1(20),2(8),9,11,13(21),14,16,18-octaene-6,7-diol
Traditional Namebenzo(a)pyrene diol epoxide
CAS Registry Number58917-67-2
SMILES
OC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O
InChI Identifier
InChI=1S/C20H14O3/c21-17-13-8-11-5-4-9-2-1-3-10-6-7-12(15(11)14(9)10)16(13)19-20(23-19)18(17)22/h1-8,17-22H
InChI KeyDQEPMTIXHXSFOR-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
  • Tetralin
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.019 g/lALOGPS
LogP2.83ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.83ALOGPS
logP2.6ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.14 m³·mol⁻¹ChemAxon
Polarizability32.18 ųChemAxon
Number of Rings6ChemAxon
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]+168.65931661259
DarkChem[M-H]-166.38131661259
DeepCCS[M-2H]-208.33830932474
DeepCCS[M+Na]+183.55530932474
AllCCS[M+H]+173.932859911
AllCCS[M+H-H2O]+170.532859911
AllCCS[M+NH4]+177.032859911
AllCCS[M+Na]+177.932859911
AllCCS[M-H]-178.932859911
AllCCS[M+Na-2H]-177.832859911
AllCCS[M+HCOO]-176.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxideOC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O4433.8Standard polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxideOC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O2869.4Standard non polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxideOC1C2OC2C2=C(C=C3C=CC4=C5C(C=CC2=C35)=CC=C4)C1O3342.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TMS,isomer #1C[Si](C)(C)OC1C(O)C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC21)C3=C453167.6Semi standard non polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TMS,isomer #2C[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O)C3=C453199.9Semi standard non polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,2TMS,isomer #1C[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O[Si](C)(C)C)C3=C453182.9Semi standard non polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C(O)C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC21)C3=C453416.3Semi standard non polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O)C3=C453428.0Semi standard non polar33892256
Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1C2=CC3=CC=C4C=CC=C5C=CC(=C2C2OC2C1O[Si](C)(C)C(C)(C)C)C3=C453595.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-0090000000-152c9cf2a50947f26f2c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (2 TMS) - 70eV, Positivesplash10-0kmr-7019100000-f7da140ee19b3f0897b32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Positive-QTOFsplash10-0udi-0019000000-282dfb81066da2878f732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Positive-QTOFsplash10-0udi-2089000000-db5f1c46ceefa93331392016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Positive-QTOFsplash10-05n0-1090000000-17807b407c1cd92e90ce2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Negative-QTOFsplash10-0udi-0009000000-3cebeaad6380d7f45ed82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Negative-QTOFsplash10-0udi-0049000000-ad94deb86b0fab35aece2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Negative-QTOFsplash10-0ufr-1090000000-efc7a183027b49eec6c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Negative-QTOFsplash10-0udi-0009000000-e692d58cc60b5b6120912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Negative-QTOFsplash10-0udi-0049000000-5ef0b27e7167c9cca44d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Negative-QTOFsplash10-0f7o-1091000000-684f758a5ace9d3705462021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 10V, Positive-QTOFsplash10-0udi-0049000000-649fbd314baf527362aa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 20V, Positive-QTOFsplash10-0udr-0098000000-679c99bf1e7d577c48892021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-dihydrodiol-9,10-oxide 40V, Positive-QTOFsplash10-0udr-1094000000-c9b1ce91e6e2f4a272da2021-09-25Wishart LabView Spectrum
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 ID37707
KEGG Compound IDC14853
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound41322
PDB IDNot Available
ChEBI ID30614
Food Biomarker OntologyNot Available
VMH IDM01376
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available