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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 19:12:37 UTC
Update Date2021-09-26 23:14:41 UTC
HMDB IDHMDB0258033
Secondary Accession NumbersNone
Metabolite Identification
Common Name[(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate
Description5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-3-yl propanoate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. Based on a literature review very few articles have been published on 5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-3-yl propanoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). [(8s,9s,13s,14s,17r)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate 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
Synonyms
ValueSource
5,14-Dihydroxy-15-methyltetracyclo[8.7.0.0,.0,]heptadeca-2,4,6-trien-3-yl propanoic acidGenerator
[(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoic acidGenerator
Chemical FormulaC21H28O4
Average Molecular Weight344.451
Monoisotopic Molecular Weight344.198759382
IUPAC Name5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-3-yl propanoate
Traditional Name5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-3-yl propanoate
CAS Registry NumberNot Available
SMILES
CCC(=O)OC1=C2C3CCC4(C)C(O)CCC4C3CCC2=CC(O)=C1
InChI Identifier
InChI=1S/C21H28O4/c1-3-19(24)25-17-11-13(22)10-12-4-5-14-15(20(12)17)8-9-21(2)16(14)6-7-18(21)23/h10-11,14-16,18,22-23H,3-9H2,1-2H3
InChI KeyJQMWFLSAVOSNEP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Estrane-skeleton
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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
logP4.25ALOGPS
logP4.05ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.44ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.66 m³·mol⁻¹ChemAxon
Polarizability38.83 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
DeepCCS[M+H]+186.39130932474
DeepCCS[M-H]-184.03330932474
DeepCCS[M-2H]-217.55230932474
DeepCCS[M+Na]+192.77930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
[(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoateCCC(=O)OC1=C2C3CCC4(C)C(O)CCC4C3CCC2=CC(O)=C13435.3Standard polar33892256
[(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoateCCC(=O)OC1=C2C3CCC4(C)C(O)CCC4C3CCC2=CC(O)=C12886.5Standard non polar33892256
[(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoateCCC(=O)OC1=C2C3CCC4(C)C(O)CCC4C3CCC2=CC(O)=C13139.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-05p9-4095000000-d9447e438802e345f30b2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(8S,9S,13S,14S,17R)-3,17-Dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-1-yl] propanoate GC-MS (TBDMS_2_1) - 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 ]