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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:20:55 UTC
Update Date2022-03-07 03:17:44 UTC
HMDB IDHMDB0060439
Secondary Accession Numbers
  • HMDB60439
Metabolite Identification
Common NameBenzo[a]pyrene-7,8-oxide
DescriptionBenzo[a]pyrene-7,8-oxide 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-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866060
Synonyms
ValueSource
Benzo[a]pyrene-7,8-epoxideKegg
Benzo(a)pyrene 7,8-oxideHMDB
Benzo(a)pyrene 7,8-oxide, (+-)-isomerHMDB
Benzo(a)pyrene 7,8-oxide, (6BS)-isomerHMDB
Benzo(a)pyrene 7,8-epoxideHMDB
Benzo(a)pyrene 7,8-oxide, (6BR)-isomerHMDB
Chemical FormulaC20H12O
Average Molecular Weight268.3087
Monoisotopic Molecular Weight268.088815006
IUPAC Name6-oxahexacyclo[11.6.2.0²,⁸.0⁵,⁷.0¹⁰,²⁰.0¹⁷,²¹]henicosa-1,3,8,10(20),11,13(21),14,16,18-nonaene
Traditional Namebenzo(a)pyrene 7,8-oxide
CAS Registry NumberNot Available
SMILES
O1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C12
InChI Identifier
InChI=1S/C20H12O/c1-2-11-4-5-13-10-16-14(8-9-17-20(16)21-17)15-7-6-12(3-1)18(11)19(13)15/h1-10,17,20H
InChI KeyOLLMQFHYRYHKTD-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
  • Phenanthrene
  • Naphthalene
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility1.2e-05 g/LALOGPS
logP5.19ALOGPS
logP4.47ChemAxon
logS-7.4ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.53 m³·mol⁻¹ChemAxon
Polarizability29.82 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.28231661259
DarkChem[M-H]-161.81631661259
DeepCCS[M-2H]-205.40130932474
DeepCCS[M+Na]+180.62830932474
AllCCS[M+H]+164.932859911
AllCCS[M+H-H2O]+161.232859911
AllCCS[M+NH4]+168.432859911
AllCCS[M+Na]+169.432859911
AllCCS[M-H]-171.932859911
AllCCS[M+Na-2H]-170.332859911
AllCCS[M+HCOO]-168.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyrene-7,8-oxideO1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C124274.1Standard polar33892256
Benzo[a]pyrene-7,8-oxideO1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C122605.0Standard non polar33892256
Benzo[a]pyrene-7,8-oxideO1C2C=CC3=C4C=CC5=CC=CC6=C5C4=C(C=C6)C=C3C123026.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-1090000000-4b9ffcf6ba52ad9a67722017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-7,8-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-oxide 10V, Positive-QTOFsplash10-014i-0090000000-6dd249213c7d7f2ce33b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 20V, Positive-QTOFsplash10-014i-0090000000-201806979a02653929912017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 40V, Positive-QTOFsplash10-0fb9-0090000000-b00168fdb22eae96a1352017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 10V, Negative-QTOFsplash10-014i-0090000000-1ed0e0bd5b5d9a23a8a62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 20V, Negative-QTOFsplash10-014i-0090000000-2306ec9feeafd317f3ab2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-7,8-oxide 40V, Negative-QTOFsplash10-00mo-0090000000-18478cdd5aa3249d8f5b2017-10-06Wishart 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 IDC14850
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound37455
PDB IDNot Available
ChEBI ID34563
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 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:
EPHX1
Uniprot ID:
P07099
Molecular weight:
52948.48
Reactions
Benzo[a]pyrene-7,8-oxide + Water → Benzo[a]pyrene-7,8-dioldetails