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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 18:38:54 UTC
Update Date2021-09-26 23:14:06 UTC
HMDB IDHMDB0257622
Secondary Accession NumbersNone
Metabolite Identification
Common Name[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Description{2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulfonic acid belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. {2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). [(3s,8r,9s,10s,13s,14s)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically [(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate 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
{2,15-dimethyl-14-oxotetracyclo[8.7.0.0,.0,]heptadecan-5-yl}oxidanesulfonateGenerator
{2,15-dimethyl-14-oxotetracyclo[8.7.0.0,.0,]heptadecan-5-yl}oxidanesulphonateGenerator
{2,15-dimethyl-14-oxotetracyclo[8.7.0.0,.0,]heptadecan-5-yl}oxidanesulphonic acidGenerator
{2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulfonateGenerator
{2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulphonateGenerator
{2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulphonic acidGenerator
Chemical FormulaC19H30O5S
Average Molecular Weight370.5
Monoisotopic Molecular Weight370.18139524
IUPAC Name{2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulfonic acid
Traditional Name{2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CCC4CC(CCC34C)OS(O)(=O)=O)C1CCC2=O
InChI Identifier
InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)
InChI KeyZMITXKRGXGRMKS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • Androstane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP0.45ALOGPS
logP3.82ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.8 m³·mol⁻¹ChemAxon
Polarizability40.38 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-2H]-219.73430932474
DeepCCS[M+Na]+195.58130932474
AllCCS[M+H]+190.432859911
AllCCS[M+H-H2O]+188.032859911
AllCCS[M+NH4]+192.732859911
AllCCS[M+Na]+193.432859911
AllCCS[M-H]-187.632859911
AllCCS[M+Na-2H]-188.132859911
AllCCS[M+HCOO]-188.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfateCC12CCC3C(CCC4CC(CCC34C)OS(O)(=O)=O)C1CCC2=O3532.2Standard polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfateCC12CCC3C(CCC4CC(CCC34C)OS(O)(=O)=O)C1CCC2=O2574.4Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfateCC12CCC3C(CCC4CC(CCC34C)OS(O)(=O)=O)C1CCC2=O3126.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C)CCC43C)C1CCC2=O3118.2Semi standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C)CCC43C)C1CCC2=O2983.9Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C)CCC43C)C1CCC2=O3721.3Standard polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TMS,isomer #2CC12CCC3C(CCC4CC(OS(=O)(=O)O)CCC43C)C1CC=C2O[Si](C)(C)C3099.9Semi standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TMS,isomer #2CC12CCC3C(CCC4CC(OS(=O)(=O)O)CCC43C)C1CC=C2O[Si](C)(C)C2812.2Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TMS,isomer #2CC12CCC3C(CCC4CC(OS(=O)(=O)O)CCC43C)C1CC=C2O[Si](C)(C)C3771.0Standard polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,2TMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C)CCC43C)C1CC=C2O[Si](C)(C)C3117.6Semi standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,2TMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C)CCC43C)C1CC=C2O[Si](C)(C)C3033.0Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,2TMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C)CCC43C)C1CC=C2O[Si](C)(C)C3701.8Standard polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TBDMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC43C)C1CCC2=O3345.7Semi standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TBDMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC43C)C1CCC2=O3304.3Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TBDMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC43C)C1CCC2=O3843.6Standard polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TBDMS,isomer #2CC12CCC3C(CCC4CC(OS(=O)(=O)O)CCC43C)C1CC=C2O[Si](C)(C)C(C)(C)C3364.0Semi standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TBDMS,isomer #2CC12CCC3C(CCC4CC(OS(=O)(=O)O)CCC43C)C1CC=C2O[Si](C)(C)C(C)(C)C3078.0Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,1TBDMS,isomer #2CC12CCC3C(CCC4CC(OS(=O)(=O)O)CCC43C)C1CC=C2O[Si](C)(C)C(C)(C)C3920.7Standard polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,2TBDMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC43C)C1CC=C2O[Si](C)(C)C(C)(C)C3571.7Semi standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,2TBDMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC43C)C1CC=C2O[Si](C)(C)C(C)(C)C3571.1Standard non polar33892256
[(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate,2TBDMS,isomer #1CC12CCC3C(CCC4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC43C)C1CC=C2O[Si](C)(C)C(C)(C)C3879.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - [(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0198000000-ef3a205ce5e72a8cd0a02021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - [(3S,8R,9S,10S,13S,14S)-10,13-Dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart 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 Compound246
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 ]