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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:54:59 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060341
Secondary Accession Numbers
  • HMDB60341
Metabolite Identification
Common Name1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene
Description1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene exists in all living organisms, ranging from bacteria to humans. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Structure
Data?1563866047
SynonymsNot Available
Chemical FormulaC20H16O
Average Molecular Weight272.3404
Monoisotopic Molecular Weight272.120115134
IUPAC Name12,19-dimethyl-6-oxapentacyclo[9.8.0.0²,⁸.0⁵,⁷.0¹³,¹⁸]nonadeca-1(19),2(8),3,9,11,13,15,17-octaene
Traditional Name12,19-dimethyl-6-oxapentacyclo[9.8.0.0²,⁸.0⁵,⁷.0¹³,¹⁸]nonadeca-1(19),2(8),3,9,11,13,15,17-octaene
CAS Registry NumberNot Available
SMILES
CC1=C2C=CC3=C(C=CC4OC34)C2=C(C)C2=CC=CC=C12
InChI Identifier
InChI=1S/C20H16O/c1-11-13-5-3-4-6-14(13)12(2)19-15(11)7-8-17-16(19)9-10-18-20(17)21-18/h3-10,18,20H,1-2H3
InChI KeyUZKWBBZEYBCHIN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Anthracene
  • 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 Solubility2.2e-05 g/LALOGPS
logP5.24ALOGPS
logP5.16ChemAxon
logS-7.1ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.85 m³·mol⁻¹ChemAxon
Polarizability31.19 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]+163.22831661259
DarkChem[M-H]-162.64531661259
DeepCCS[M-2H]-197.21130932474
DeepCCS[M+Na]+172.77630932474
AllCCS[M+H]+165.632859911
AllCCS[M+H-H2O]+161.832859911
AllCCS[M+NH4]+169.132859911
AllCCS[M+Na]+170.132859911
AllCCS[M-H]-173.132859911
AllCCS[M+Na-2H]-171.832859911
AllCCS[M+HCOO]-170.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxireneCC1=C2C=CC3=C(C=CC4OC34)C2=C(C)C2=CC=CC=C123843.9Standard polar33892256
1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxireneCC1=C2C=CC3=C(C=CC4OC34)C2=C(C)C2=CC=CC=C122593.1Standard non polar33892256
1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxireneCC1=C2C=CC3=C(C=CC4OC34)C2=C(C)C2=CC=CC=C122828.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-0190000000-2d545c03ff847ffe89ec2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 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 - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 10V, Positive-QTOFsplash10-00di-0090000000-2a16a794047535245ee62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 20V, Positive-QTOFsplash10-05fr-0090000000-e6a1bce61fdabaf555512017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 40V, Positive-QTOFsplash10-0zi0-0490000000-8f802df6e498892784bf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 10V, Negative-QTOFsplash10-00di-0090000000-1b00db8ec13edbabb3b82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 20V, Negative-QTOFsplash10-00di-0090000000-ac6f4dfbf1dd0abc53912017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene 40V, Negative-QTOFsplash10-0ki7-0090000000-a687b57eb267bb9dbe022017-10-06Wishart 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 IDC19489
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53297434
PDB IDNot Available
ChEBI ID82517
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
1a,11b-Dihydro-4,9-dimethylbenz[a]anthra[3,4-b]oxirene + Water → trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracenedetails