Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 01:51:42 UTC
Update Date2019-07-23 07:18:36 UTC
HMDB IDHMDB0062469
Secondary Accession Numbers
  • HMDB62469
Metabolite Identification
Common NameBenzo[a]pyrene
DescriptionBenzo[a]pyrene, also known as 3,4-Benzopyrene or 3,4-BP, is classified as a member of the Benzopyrenes. Benzopyrenes are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system. Benzo[a]pyrene is formally rated as a carcinogenic (IARC 1) potentially toxic compound. Benzo[a]pyrene is a crystalline, aromatic hydrocarbon consisting of five fused benzene rings and formed during the incomplete combustion of organic matter. Benzo[a]pyrene is primarily found in gasoline and diesel exhaust, cigarette smoke, coal tar and coal tar pitch, charcoal-broiled foods and certain other foods, amino acids, fatty acids and carbohydrate pyrolysis products, soot smoke, creosote oil, petroleum asphalt and shale oils. This substance is used only for research purposes. Benzo[a]pyrene is reasonably anticipated to be a human carcinogen (NCI05). Its diol epoxide metabolites (more commonly known as BPDE) react and bind to DNA, resulting in mutations and eventually cancer. It is listed as a Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already connected to soot. [Wikipedia ]
Structure
Data?1563866316
Synonyms
ValueSource
(b(a)p)ChEBI
3,4-BenzopyreneChEBI
3,4-BenzpyreneChEBI
3,4-BPChEBI
Benzo(a)pyreneChEBI
Benzo[def]chryseneChEBI
BenzpyreneChEBI
BPChEBI
3,4 BenzpyreneHMDB
3,4 BenzopyreneHMDB
Chemical FormulaC20H12
Average Molecular Weight252.3093
Monoisotopic Molecular Weight252.093900384
IUPAC Namepentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene
Traditional Namepentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene
CAS Registry Number50-32-8
SMILES
C1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C3
InChI Identifier
InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
InChI KeyFMMWHPNWAFZXNH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzopyrenes. These are organic compounds containing a benzene fused to a pyrene(benzo[def]phenanthrene) ring system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassBenzopyrenes
Direct ParentBenzopyrenes
Alternative Parents
Substituents
  • Benzo-a-pyrene
  • Chrysene
  • Phenanthrene
  • Anthracene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • 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 Solubility1.2e-06 g/lALOGPS
LogP6.39ALOGPS
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available152.046http://allccs.zhulab.cn/database/detail?ID=AllCCS00002037
Predicted Molecular Properties
PropertyValueSource
logP6.39ALOGPS
logP5.27ChemAxon
logS-8.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.17 m³·mol⁻¹ChemAxon
Polarizability29.09 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.24531661259
DarkChem[M-H]-157.75531661259
DeepCCS[M-2H]-202.78130932474
DeepCCS[M+Na]+177.90430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyreneC1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C34071.5Standard polar33892256
Benzo[a]pyreneC1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C32798.7Standard non polar33892256
Benzo[a]pyreneC1=CC=C2C(=C1)C=C1C=CC3=C4C(C=CC2=C14)=CC=C32805.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)splash10-0udi-0590000000-6a1e4169eaee2450b6aa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)splash10-0udi-0390000000-d87401bcab72c45a1d872017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzo[a]pyrene CI-B (Non-derivatized)splash10-0udi-0090000000-aebdc23a6e4cb494681e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)splash10-0udi-0590000000-6a1e4169eaee2450b6aa2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzo[a]pyrene EI-B (Non-derivatized)splash10-0udi-0390000000-d87401bcab72c45a1d872018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzo[a]pyrene CI-B (Non-derivatized)splash10-0udi-0090000000-aebdc23a6e4cb494681e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0090000000-4ed81317d745f20ae6d32017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-0290000000-21f41e03667be1e6edca2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Positive-QTOFsplash10-0udi-0090000000-f612ac63f25ab09a3fb72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Positive-QTOFsplash10-0udi-0090000000-da5273239d688cd66f492016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Positive-QTOFsplash10-0ufr-0090000000-fb6dcdd11a97e4d744792016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Negative-QTOFsplash10-0udi-0090000000-31f8cde7b8fb38348ad02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Negative-QTOFsplash10-0udi-0090000000-31f8cde7b8fb38348ad02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Negative-QTOFsplash10-0udi-0090000000-f5fc2a06e6c04b87e62f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Negative-QTOFsplash10-0udi-0090000000-969da6c938a324fffb4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Negative-QTOFsplash10-0udi-0090000000-969da6c938a324fffb4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Negative-QTOFsplash10-0udi-0090000000-969da6c938a324fffb4f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 10V, Positive-QTOFsplash10-0udi-0090000000-b5f9e841f69a96c6392a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 20V, Positive-QTOFsplash10-0udi-0090000000-b5f9e841f69a96c6392a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene 40V, Positive-QTOFsplash10-0udi-0090000000-d38a61935d2a229c0c1f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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 IDNot Available
KEGG Compound IDC07535
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzo(a)pyrene
METLIN IDNot Available
PubChem Compound2336
PDB IDNot Available
ChEBI ID29865
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 ReferencesNot Available