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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 23:43:54 UTC
Update Date2021-09-26 23:18:08 UTC
HMDB IDHMDB0260179
Secondary Accession NumbersNone
Metabolite Identification
Common Name(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one
Description5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3-dien-14-one belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Based on a literature review very few articles have been published on 5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3-dien-14-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (8r,9s,13s,14s)-3-hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3h-cyclopenta[a]phenanthren-17-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H24O2
Average Molecular Weight272.388
Monoisotopic Molecular Weight272.177630013
IUPAC Name5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-dien-14-one
Traditional Name5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-dien-14-one
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O
InChI Identifier
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,12,14-16,19H,2,4,6-10H2,1H3
InChI KeyPPVLHOVXXOMTJL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP2.1ALOGPS
logP2.81ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.44ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.88 m³·mol⁻¹ChemAxon
Polarizability31.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+169.55232859911
AllCCS[M+H-H2O]+166.19832859911
AllCCS[M+Na]+173.55632859911
AllCCS[M+NH4]+172.66232859911
AllCCS[M-H]-174.26632859911
AllCCS[M+Na-2H]-174.12932859911
AllCCS[M+HCOO]-174.10932859911
DeepCCS[M-2H]-198.57330932474
DeepCCS[M+Na]+174.10130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-oneCC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O3275.6Standard polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-oneCC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O2446.4Standard non polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-oneCC12CCC3C(CCC4=C3C=CC(O)C4)C1CCC2=O2556.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)CC(O[Si](C)(C)C)C=C42635.1Semi standard non polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)CC(O[Si](C)(C)C)C=C42531.2Standard non polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TMS,isomer #1CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C)CC(O[Si](C)(C)C)C=C43004.1Standard polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C=C43135.4Semi standard non polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C=C42921.1Standard non polar33892256
(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one,2TBDMS,isomer #1CC12CCC3C4=C(CCC3C1CC=C2O[Si](C)(C)C(C)(C)C)CC(O[Si](C)(C)C(C)(C)C)C=C43264.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ox-0590000000-d754fc3aec6e8e2ffb0b2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]