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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:53:54 UTC
Update Date2021-09-14 15:37:54 UTC
HMDB IDHMDB0060091
Secondary Accession Numbers
  • HMDB60091
Metabolite Identification
Common NameBenzo[a]pyrene-4,5-oxide
DescriptionBenzo[a]pyrene-4,5-oxide belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. Benzo[a]pyrene-4,5-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzo[a]pyrene-4,5-oxide exists in all living organisms, ranging from bacteria to humans. These are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzophenanthrene.
Structure
Data?1563866014
Synonyms
ValueSource
Benzo[a]pyrene-4,5-epoxideKegg
3b,4a-Dihydrobenzo(1,2)pyreno(4,5-b)oxireneHMDB
4,5-Dihydro-4,5-epoxybenzo(a)pyreneHMDB
Benzo(a)pyrene 4,5-epoxide, (+-)-isomerHMDB
Benzo(a)pyrene 4,5-oxideHMDB
Benzo(a)pyrene 4,5-epoxideMeSH
Chemical FormulaC20H12O
Average Molecular Weight268.3087
Monoisotopic Molecular Weight268.088815006
IUPAC Name18-oxahexacyclo[10.7.2.0³,⁸.0⁹,²⁰.0¹⁶,²¹.0¹⁷,¹⁹]henicosa-1,3,5,7,9(20),10,12(21),13,15-nonaene
Traditional Namebenzo(a)pyrene 4,5-oxide
CAS Registry NumberNot Available
SMILES
O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3
InChI Identifier
InChI=1S/C20H12O/c1-2-6-13-12(4-1)10-16-18-14(13)9-8-11-5-3-7-15(17(11)18)19-20(16)21-19/h1-10,19-20H
InChI KeyXGZQLNASOQVQTD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassChrysenes
Direct ParentChrysenes
Alternative Parents
Substituents
  • Chrysene
  • 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
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 Solubility1.6e-05 g/LALOGPS
logP10(5.24) g/LALOGPS
logP10(4.52) g/LChemAxon
logS10(-7.2) g/LALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.9 m³·mol⁻¹ChemAxon
Polarizability29.84 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]+158.21231661259
DarkChem[M-H]-160.09831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzo[a]pyrene-4,5-oxideO1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C33916.5Standard polar33892256
Benzo[a]pyrene-4,5-oxideO1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C32596.8Standard non polar33892256
Benzo[a]pyrene-4,5-oxideO1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C32966.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-4,5-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0090000000-a0acee16644b56de8a872017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzo[a]pyrene-4,5-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-4,5-oxide 10V, Negative-QTOFsplash10-014i-0090000000-a54043fd1ab8580b6ed22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 20V, Negative-QTOFsplash10-014i-0090000000-9869044ce7dbcc2941752015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 40V, Negative-QTOFsplash10-00ou-0090000000-ebe5c29fe92744c283502015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 10V, Positive-QTOFsplash10-014i-0090000000-a5fc140110d675a8f67f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 20V, Positive-QTOFsplash10-014i-0090000000-265bb670b8409fa79f1a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzo[a]pyrene-4,5-oxide 40V, Positive-QTOFsplash10-0ufu-1090000000-8be0bcddc8e600a81d8f2015-09-15Wishart 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 IDC14851
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound37786
PDB IDNot Available
ChEBI ID34560
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. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

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.