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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 05:23:35 UTC
Update Date2021-09-14 15:41:24 UTC
HMDB IDHMDB0062657
Secondary Accession Numbers
  • HMDB62657
Metabolite Identification
Common NameEpiandrosterone sulfate
DescriptionEpiandrosterone sulfate, also known as (3beta,5alpha)-17-oxoandrostan-3-yl hydrogen sulfate or epiandrosterone sulphuric acid, is a member of the class of compounds known as sulfated steroids. Sulfated steroids are sterol lipids containing a sulfate group attached to the steroid skeleton. Epiandrosterone sulfate is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). Epiandrosterone sulfate can be synthesized from 5alpha-androstane and synthesized into epiandrosterone. Epiandrosterone sulfate can be found in blood and feces.
Structure
Data?1563866343
Synonyms
ValueSource
(3beta,5alpha)-17-Oxoandrostan-3-yl hydrogen sulfateChEBI
(3b,5a)-17-Oxoandrostan-3-yl hydrogen sulfateGenerator
(3b,5a)-17-Oxoandrostan-3-yl hydrogen sulfuric acidGenerator
(3b,5a)-17-Oxoandrostan-3-yl hydrogen sulphateGenerator
(3b,5a)-17-Oxoandrostan-3-yl hydrogen sulphuric acidGenerator
(3beta,5alpha)-17-Oxoandrostan-3-yl hydrogen sulfuric acidGenerator
(3beta,5alpha)-17-Oxoandrostan-3-yl hydrogen sulphateGenerator
(3beta,5alpha)-17-Oxoandrostan-3-yl hydrogen sulphuric acidGenerator
(3Β,5α)-17-oxoandrostan-3-yl hydrogen sulfateGenerator
(3Β,5α)-17-oxoandrostan-3-yl hydrogen sulfuric acidGenerator
(3Β,5α)-17-oxoandrostan-3-yl hydrogen sulphateGenerator
(3Β,5α)-17-oxoandrostan-3-yl hydrogen sulphuric acidGenerator
Epiandrosterone sulfuric acidGenerator
Epiandrosterone sulphateGenerator
Epiandrosterone sulphuric acidGenerator
3β,5α)-3-(Sulfooxy)androstan-17-oneHMDB
3β-Hydroxy-5α-androstan-17-one 3-sulfateHMDB
3β-Hydroxy-5α-androstan-17-one monosulfateHMDB
3β-Hydroxy-5α-androstan-17-one sulfateHMDB
3β-Sulfate-5α-androstan-17-oneHMDB
3beta,5alpha)-3-(Sulfooxy)androstan-17-oneHMDB
3beta-Hydroxy-5alpha-androstan-17-one 3-sulfateHMDB
3beta-Hydroxy-5alpha-androstan-17-one monosulfateHMDB
3beta-Hydroxy-5alpha-androstan-17-one sulfateHMDB
3beta-Sulfate-5alpha-androstan-17-oneHMDB
Epiandrosterone 3beta-sulfateHMDB
Epi-Androsterone sulfateHMDB
Epiandrosterone 3β-sulfateHMDB
Epiandrosterone sulfateHMDB
Isoandrosterone sulfateHMDB
Chemical FormulaC19H30O5S
Average Molecular Weight370.5
Monoisotopic Molecular Weight370.18139524
IUPAC Name[(1S,2S,5S,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2S,5S,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxidanesulfonic acid
CAS Registry Number977-35-5
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](CC[C@]12C)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-/m0/s1
InChI KeyZMITXKRGXGRMKS-LUJOEAJASA-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0048 g/lALOGPS
LogP0.45ALOGPS
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
Polarizability40.5 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]+188.2531661259
DarkChem[M-H]-180.97631661259
DeepCCS[M-2H]-223.65430932474
DeepCCS[M+Na]+198.04630932474
AllCCS[M+H]+189.832859911
AllCCS[M+H-H2O]+187.432859911
AllCCS[M+NH4]+192.032859911
AllCCS[M+Na]+192.732859911
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
Epiandrosterone sulfate[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](CC[C@]12C)OS(O)(=O)=O3214.2Standard polar33892256
Epiandrosterone sulfate[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](CC[C@]12C)OS(O)(=O)=O2906.0Standard non polar33892256
Epiandrosterone sulfate[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](CC[C@]12C)OS(O)(=O)=O3154.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epiandrosterone sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3104.8Semi standard non polar33892256
Epiandrosterone sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3016.3Standard non polar33892256
Epiandrosterone sulfate,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O3797.1Standard polar33892256
Epiandrosterone sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3074.9Semi standard non polar33892256
Epiandrosterone sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2848.6Standard non polar33892256
Epiandrosterone sulfate,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3829.1Standard polar33892256
Epiandrosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3103.7Semi standard non polar33892256
Epiandrosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3070.7Standard non polar33892256
Epiandrosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C3742.0Standard polar33892256
Epiandrosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13329.3Semi standard non polar33892256
Epiandrosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13337.2Standard non polar33892256
Epiandrosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C13919.5Standard polar33892256
Epiandrosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3332.0Semi standard non polar33892256
Epiandrosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3116.1Standard non polar33892256
Epiandrosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3979.4Standard polar33892256
Epiandrosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3577.9Semi standard non polar33892256
Epiandrosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3609.4Standard non polar33892256
Epiandrosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3910.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0198000000-4c5a7a41e009f264e2de2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone 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 - Epiandrosterone sulfate 10V, Positive-QTOFsplash10-00di-0049000000-3cadfd36eaaf2fc69cb22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 20V, Positive-QTOFsplash10-00di-0090000000-84d65540e664bb0f62a42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 40V, Positive-QTOFsplash10-03xr-2590000000-495c370c609ab6e362eb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 10V, Negative-QTOFsplash10-014i-0029000000-3188acd4a8b538e293d12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 20V, Negative-QTOFsplash10-0079-0092000000-00b2d0b50c0fd74a0b0d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 40V, Negative-QTOFsplash10-06zi-6090000000-6392ae6c8be227f3ff7c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 10V, Positive-QTOFsplash10-00di-0019000000-ed6f6b38f66a512fd98c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 20V, Positive-QTOFsplash10-0fk9-0292000000-16d0ae2e88a442fd375b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 40V, Positive-QTOFsplash10-052b-3920000000-49e4315f36f0eafbe6ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 10V, Negative-QTOFsplash10-014i-0009000000-0295bc1386cdfbdd92bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 20V, Negative-QTOFsplash10-014i-1009000000-4b958c48d4c246f8639b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone sulfate 40V, Negative-QTOFsplash10-0002-9005000000-ccff0fd3b8b51e4232062021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB034849
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9929317
PDB IDNot Available
ChEBI ID83040
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.