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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-11-30 15:51:24 UTC
Update Date2022-09-22 18:34:21 UTC
HMDB IDHMDB0013232
Secondary Accession Numbers
  • HMDB13232
Metabolite Identification
Common NameEtiocholanolone sulfate
DescriptionEtiocholanolone sulfate belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Etiocholanolone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582753103
Synonyms
ValueSource
Etiocholanolone sulfuric acidGenerator
Etiocholanolone sulphateGenerator
Etiocholanolone sulphuric acidGenerator
Chemical FormulaC19H30O5S
Average Molecular Weight370.504
Monoisotopic Molecular Weight370.18139476
IUPAC Name[(2S,5R,7R,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid
Traditional Name[(2S,5R,7R,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
[H][C@]12CCC3C4CCC(=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@H](C2)OS(O)(=O)=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)/t12-,13-,14?,15?,16?,18+,19+/m1/s1
InChI KeyZMITXKRGXGRMKS-ZQSLQREJSA-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
Process
Role
Physical Properties
StateSolid
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 Solubility0.0048 g/LALOGPS
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
Polarizability39.86 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]+185.63431661259
DarkChem[M-H]-181.61231661259
DeepCCS[M-2H]-230.18930932474
DeepCCS[M+Na]+205.50830932474
AllCCS[M+H]+190.332859911
AllCCS[M+H-H2O]+187.832859911
AllCCS[M+NH4]+192.532859911
AllCCS[M+Na]+193.232859911
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
Etiocholanolone sulfate[H][C@]12CCC3C4CCC(=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@H](C2)OS(O)(=O)=O3315.7Standard polar33892256
Etiocholanolone sulfate[H][C@]12CCC3C4CCC(=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@H](C2)OS(O)(=O)=O2758.2Standard non polar33892256
Etiocholanolone sulfate[H][C@]12CCC3C4CCC(=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@H](C2)OS(O)(=O)=O3112.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Etiocholanolone sulfate,1TMS,isomer #1C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]34C)C1CCC2=O3080.8Semi standard non polar33892256
Etiocholanolone sulfate,1TMS,isomer #1C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]34C)C1CCC2=O3008.3Standard non polar33892256
Etiocholanolone sulfate,1TMS,isomer #1C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]34C)C1CCC2=O3744.9Standard polar33892256
Etiocholanolone sulfate,1TMS,isomer #2C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]34C)C1CC=C2O[Si](C)(C)C3063.4Semi standard non polar33892256
Etiocholanolone sulfate,1TMS,isomer #2C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]34C)C1CC=C2O[Si](C)(C)C2833.8Standard non polar33892256
Etiocholanolone sulfate,1TMS,isomer #2C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]34C)C1CC=C2O[Si](C)(C)C3790.6Standard polar33892256
Etiocholanolone sulfate,2TMS,isomer #1C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]34C)C1CC=C2O[Si](C)(C)C3090.5Semi standard non polar33892256
Etiocholanolone sulfate,2TMS,isomer #1C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]34C)C1CC=C2O[Si](C)(C)C3064.9Standard non polar33892256
Etiocholanolone sulfate,2TMS,isomer #1C[C@]12CCC3C(CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@]34C)C1CC=C2O[Si](C)(C)C3724.5Standard polar33892256
Etiocholanolone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1CC[C@]2(C)C3CC[C@]4(C)C(=O)CCC4C3CC[C@@H]2C13305.9Semi standard non polar33892256
Etiocholanolone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1CC[C@]2(C)C3CC[C@]4(C)C(=O)CCC4C3CC[C@@H]2C13334.8Standard non polar33892256
Etiocholanolone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@@H]1CC[C@]2(C)C3CC[C@]4(C)C(=O)CCC4C3CC[C@@H]2C13868.2Standard polar33892256
Etiocholanolone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCC2C3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)C3CC[C@]12C3312.1Semi standard non polar33892256
Etiocholanolone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCC2C3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)C3CC[C@]12C3102.3Standard non polar33892256
Etiocholanolone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCC2C3CC[C@@H]4C[C@H](OS(=O)(=O)O)CC[C@]4(C)C3CC[C@]12C3941.1Standard polar33892256
Etiocholanolone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3550.6Semi standard non polar33892256
Etiocholanolone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3606.8Standard non polar33892256
Etiocholanolone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2C3CC[C@@H]4C[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3902.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanolone sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0597-0198000000-bbbfb8cca92c4b7515712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanolone sulfate 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 - Etiocholanolone sulfate 10V, Positive-QTOFsplash10-00di-0049000000-3cadfd36eaaf2fc69cb22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 20V, Positive-QTOFsplash10-00di-0090000000-84d65540e664bb0f62a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 40V, Positive-QTOFsplash10-03xr-2590000000-495c370c609ab6e362eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 10V, Negative-QTOFsplash10-014i-0029000000-3188acd4a8b538e293d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 20V, Negative-QTOFsplash10-0079-0092000000-00b2d0b50c0fd74a0b0d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 40V, Negative-QTOFsplash10-06zi-6090000000-6392ae6c8be227f3ff7c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 10V, Negative-QTOFsplash10-014i-0009000000-0295bc1386cdfbdd92bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 20V, Negative-QTOFsplash10-014i-0009000000-0295bc1386cdfbdd92bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 40V, Negative-QTOFsplash10-00kb-9018000000-a7cdea751ac1fefcd90e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 10V, Positive-QTOFsplash10-00di-0029000000-c5b0e18d15977249e0602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 20V, Positive-QTOFsplash10-05fr-1694000000-2f884de5df30639555102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanolone sulfate 40V, Positive-QTOFsplash10-0a4i-1891000000-504944746dfada6049792021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029348
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481659
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. PLAGER JE: THE BINDING OF ANDROSTERONE SULFATE, ETHIOCHOLANOLONE SULFATE, AND DEHYDROISOANDROSTERONE SULFATE BY HUMAN PLASMA PROTEIN. J Clin Invest. 1965 Jul;44:1234-9. [PubMed:14328399 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.