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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:01:40 UTC
Update Date2019-07-23 07:14:18 UTC
HMDB IDHMDB0060422
Secondary Accession Numbers
  • HMDB60422
Metabolite Identification
Common Name7,12-Dimethylbenz[a]anthracene 5,6-oxide
Description7,12-Dimethylbenz[a]anthracene 5,6-oxide, also known as dmba-5,6-epoxide, belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring. 7,12-Dimethylbenz[a]anthracene 5,6-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866058
Synonyms
ValueSource
DMBA-5,6-epoxideKegg
7,12-Dimethylbenz(a)anthracene 5,6-oxideHMDB
7,12-Dimethylbenz(a)anthracene 5,6-epoxideHMDB
Chemical FormulaC20H16O
Average Molecular Weight272.3404
Monoisotopic Molecular Weight272.120115134
IUPAC Name12,19-dimethyl-3-oxapentacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹³,¹⁸]nonadeca-1(19),5,7,9,11,13,15,17-octaene
Traditional Name12,19-dimethyl-3-oxapentacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹³,¹⁸]nonadeca-1(19),5,7,9,11,13,15,17-octaene
CAS Registry NumberNot Available
SMILES
CC1=C2C3OC3C3=CC=CC=C3C2=C(C)C2=CC=CC=C12
InChI Identifier
InChI=1S/C20H16O/c1-11-13-7-3-4-8-14(13)12(2)18-17(11)15-9-5-6-10-16(15)19-20(18)21-19/h3-10,19-20H,1-2H3
InChI KeyHVGNLIKFFBYBQM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzoxepines. Dibenzoxepines are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxepines
Sub ClassDibenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Phenanthrene
  • Naphthalene
  • Benzenoid
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.4e-05 g/LALOGPS
logP5.06ALOGPS
logP5.21ChemAxon
logS-6.5ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.22 m³·mol⁻¹ChemAxon
Polarizability31.22 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-0090000000-32cc62b8a79c761d14bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-2bbeb162f7114c97d7efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0190000000-4a8492adba54e4d0ca3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdj-3970000000-9f28bd98cc7bb904ea13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-077be67002cf9ef77d6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c66cf32d9bf919e4630cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kk9-0090000000-215940940323a1c17d49Spectrum
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19604
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound38354
PDB IDNot Available
ChEBI ID82590
Food Biomarker OntologyNot Available
VMH 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
7,12-Dimethylbenz[a]anthracene 5,6-oxide + Water → trans-5,6-Dihydro-5,6-dihydroxy-7,12-dimethylbenz[a]anthracenedetails