Hmdb loader
Survey
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 Date2013-05-17 01:26:35 UTC
Update Date2022-03-07 03:17:46 UTC
HMDB IDHMDB0060517
Secondary Accession Numbers
  • HMDB60517
Metabolite Identification
Common Nametrans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene
Descriptiontrans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene, also known as trans-dmba-3,4-dihydrodiol, belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866070
Synonyms
ValueSource
trans-DMBA-3,4-dihydrodiolKegg
Chemical FormulaC20H18O2
Average Molecular Weight290.3557
Monoisotopic Molecular Weight290.13067982
IUPAC Name(3S,4S)-7,12-dimethyl-3,4-dihydrotetraphene-3,4-diol
Traditional Name(3S,4S)-7,12-dimethyl-3,4-dihydrotetraphene-3,4-diol
CAS Registry NumberNot Available
SMILES
CC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C12
InChI Identifier
InChI=1S/C20H18O2/c1-11-13-5-3-4-6-14(13)12(2)19-15(11)7-8-17-16(19)9-10-18(21)20(17)22/h3-10,18,20-22H,1-2H3/t18-,20-/m0/s1
InChI KeyYZIIKMBFHLJAFT-ICSRJNTNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthrols
Direct ParentPhenanthrols
Alternative Parents
Substituents
  • Phenanthrol
  • Anthracene
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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 Solubility0.0017 g/LALOGPS
logP3.91ALOGPS
logP4ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)13.17ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.36 m³·mol⁻¹ChemAxon
Polarizability33.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+166.23631661259
DarkChem[M-H]-164.26231661259
DeepCCS[M-2H]-206.39530932474
DeepCCS[M+Na]+181.62230932474
AllCCS[M+H]+171.332859911
AllCCS[M+H-H2O]+167.732859911
AllCCS[M+NH4]+174.732859911
AllCCS[M+Na]+175.632859911
AllCCS[M-H]-176.832859911
AllCCS[M+Na-2H]-176.032859911
AllCCS[M+HCOO]-175.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthraceneCC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C124107.7Standard polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthraceneCC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C122965.9Standard non polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthraceneCC1=C2C=CC3=C(C=C[C@H](O)[C@H]3O)C2=C(C)C2=CC=CC=C123162.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C)[C@@H](O)C3=CC=C123031.0Semi standard non polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TMS,isomer #2CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O)[C@@H](O[Si](C)(C)C)C3=CC=C122986.3Semi standard non polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,2TMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C3=CC=C122947.8Semi standard non polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TBDMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)C3=CC=C123217.6Semi standard non polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,1TBDMS,isomer #2CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C3=CC=C123187.6Semi standard non polar33892256
trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene,2TBDMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C3=CC=C123348.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (Non-derivatized) - 70eV, Positivesplash10-08mi-0090000000-8a0befd1db0c6609edc12017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene GC-MS (2 TMS) - 70eV, Positivesplash10-01ba-5009300000-7f9e2570d5488522b8682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 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 - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 10V, Positive-QTOFsplash10-0006-0090000000-c698bbac9128847200332017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 20V, Positive-QTOFsplash10-06r6-0090000000-5124a7412bb55908277c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 40V, Positive-QTOFsplash10-1029-0190000000-aaba1154bc60c670e1832017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 10V, Negative-QTOFsplash10-000i-0090000000-f12b2d0d9279d10da32b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 20V, Negative-QTOFsplash10-000i-0090000000-b8bd2cd25f6d727310c22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-3,4-Dihydro-3,4-dihydroxy-7,12-dimethylbenz[a]anthracene 40V, Negative-QTOFsplash10-024r-1090000000-35537bdb8ef5014ec0342017-10-06Wishart 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 IDC19490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound156317
PDB IDNot Available
ChEBI ID82518
Food Biomarker OntologyNot Available
VMH IDM03032
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