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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:34:07 UTC
Update Date2022-03-07 03:17:50 UTC
HMDB IDHMDB0062223
Secondary Accession Numbers
  • HMDB62223
Metabolite Identification
Common Name(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol
Description(3S,5R,6R,7S)-12,19-dimethyl-4-oxapentacyclo[9.8.0.0²,⁸.0³,⁵.0¹³,¹⁸]nonadeca-1(19),2(8),9,11,13,15,17-heptaene-6,7-diol 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 (3S,5R,6R,7S)-12,19-dimethyl-4-oxapentacyclo[9.8.0.0²,⁸.0³,⁵.0¹³,¹⁸]nonadeca-1(19),2(8),9,11,13,15,17-heptaene-6,7-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866282
Synonyms
ValueSource
(1Aalpha,2b,3a,11calpha)-1a,2,3,11C-tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diolGenerator
(1Aalpha,2β,3α,11calpha)-1a,2,3,11C-tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diolGenerator
Chemical FormulaC20H18O3
Average Molecular Weight306.361
Monoisotopic Molecular Weight306.12559444
IUPAC Name(3S,5R,6R,7S)-12,19-dimethyl-4-oxapentacyclo[9.8.0.0^{2,8}.0^{3,5}.0^{13,18}]nonadeca-1(19),2(8),9,11,13,15,17-heptaene-6,7-diol
Traditional Name(3S,5R,6R,7S)-12,19-dimethyl-4-oxapentacyclo[9.8.0.0^{2,8}.0^{3,5}.0^{13,18}]nonadeca-1(19),2(8),9,11,13,15,17-heptaene-6,7-diol
CAS Registry Number86941-58-4
SMILES
[H][C@@]12O[C@]1([H])[C@]([H])(O)[C@@]([H])(O)C1=C2C2=C(C)C3=CC=CC=C3C(C)=C2C=C1
InChI Identifier
InChI=1S/C20H18O3/c1-9-11-5-3-4-6-12(11)10(2)15-13(9)7-8-14-16(15)19-20(23-19)18(22)17(14)21/h3-8,17-22H,1-2H3/t17-,18+,19-,20+/m0/s1
InChI KeySZIWZGXOWBSPTO-ZGXWSNOMSA-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
  • Tetralin
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 g/lALOGPS
LogP2.96ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.96ALOGPS
logP3.29ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.81ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.46 m³·mol⁻¹ChemAxon
Polarizability33.67 ųChemAxon
Number of Rings5ChemAxon
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]+168.8931661259
DarkChem[M-H]-167.65231661259
DeepCCS[M-2H]-206.13630932474
DeepCCS[M+Na]+180.44530932474
AllCCS[M+H]+176.032859911
AllCCS[M+H-H2O]+172.632859911
AllCCS[M+NH4]+179.232859911
AllCCS[M+Na]+180.132859911
AllCCS[M-H]-181.132859911
AllCCS[M+Na-2H]-180.332859911
AllCCS[M+HCOO]-179.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol[H][C@@]12O[C@]1([H])[C@]([H])(O)[C@@]([H])(O)C1=C2C2=C(C)C3=CC=CC=C3C(C)=C2C=C14263.6Standard polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol[H][C@@]12O[C@]1([H])[C@]([H])(O)[C@@]([H])(O)C1=C2C2=C(C)C3=CC=CC=C3C(C)=C2C=C12894.0Standard non polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol[H][C@@]12O[C@]1([H])[C@]([H])(O)[C@@]([H])(O)C1=C2C2=C(C)C3=CC=CC=C3C(C)=C2C=C13172.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol,1TMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C(=CC=C12)[C@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O[C@@H]313012.9Semi standard non polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol,1TMS,isomer #2CC1=C2C=CC=CC2=C(C)C2=C3C(=CC=C12)[C@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O[C@@H]312946.7Semi standard non polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol,2TMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C(=CC=C12)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[C@@H]312963.7Semi standard non polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol,1TBDMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C(=CC=C12)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[C@@H]313210.6Semi standard non polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol,1TBDMS,isomer #2CC1=C2C=CC=CC2=C(C)C2=C3C(=CC=C12)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[C@@H]313167.9Semi standard non polar33892256
(1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol,2TBDMS,isomer #1CC1=C2C=CC=CC2=C(C)C2=C3C(=CC=C12)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[C@@H]313352.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0090000000-323fc28e67253a0cd27e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0abc-3039100000-f0937d5bfa9095d090432017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 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 - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 10V, Positive-QTOFsplash10-0a4i-0019000000-6b9612b7dd58bfb50b882017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 20V, Positive-QTOFsplash10-0a4i-1097000000-2c8384e827fd8567f0762017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 40V, Positive-QTOFsplash10-0zmi-0190000000-23a3fc6d00b6336b5dcf2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 10V, Negative-QTOFsplash10-0a4i-0009000000-b9d3d29987b86ad0418b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 20V, Negative-QTOFsplash10-0a4i-0039000000-cf4527b82de7bac434102017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 40V, Negative-QTOFsplash10-0pb9-0090000000-547198c03772c48ddb002017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 10V, Negative-QTOFsplash10-0a4i-0029000000-06d97d84f19675969eee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 20V, Negative-QTOFsplash10-0a4i-0019000000-ead838a424b7f1d0408c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 40V, Negative-QTOFsplash10-0pbi-0094000000-1a93427776742fdc09c62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 10V, Positive-QTOFsplash10-0a4i-0019000000-5ad003f886535e937ded2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 20V, Positive-QTOFsplash10-0a4i-0019000000-586e6c4dbeb77df6f9f02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (1aalpha,2beta,3alpha,11calpha)-1a,2,3,11c-Tetrahydro-6,11-dimethylbenzo[6,7]phenanthro[3,4-b]oxirene-2,3-diol 40V, Positive-QTOFsplash10-0a4i-0096000000-3eb6db11605bf00ca4ea2021-09-25Wishart LabView Spectrum
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 IDC19559
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound174597
PDB IDNot Available
ChEBI ID82558
Food Biomarker OntologyNot Available
VMH IDM00030
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available