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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000546
Secondary Accession Numbers
  • HMDB00546
Metabolite Identification
Common NameEpietiocholanolone
DescriptionEpietiocholanolone, also known as 5b-epiandrosterone or M1A, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, epietiocholanolone is considered to be a steroid. Based on a literature review very few articles have been published on Epietiocholanolone.
Structure
Data?1582752138
Synonyms
ValueSource
3b-EtiocholanoloneHMDB
3b-Hydroxy-17-oxo-5b-androstaneHMDB
3b-Hydroxy-5b-androstan-17-oneHMDB
3b-Hydroxy-5b-androstane-17-oneHMDB
3b-Hydroxyetiocholan-17-oneHMDB
5b-Androstan-3b-ol-17-oneHMDB
5b-Androstane-3b-ol-17-oneHMDB
5b-EpiandrosteroneHMDB
b-EtiocholanoloneHMDB
beta-EtiocholanoloneHMDB
Epi-5b-androsteroneHMDB
EpiaetiocholanoloneHMDB
Etiocholan-3b-ol-17-oneHMDB
M1AHMDB
Methyl-1-alphaHMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS Registry Number571-31-3
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,18+,19+/m1/s1
InChI KeyQGXBDMJGAMFCBF-XRJZGPCZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point154 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.65 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
DarkChem[M+H]+170.59331661259
DarkChem[M-H]-165.9431661259
AllCCS[M+H]+175.34532859911
AllCCS[M-H]-178.96832859911
DeepCCS[M-2H]-203.45730932474
DeepCCS[M+Na]+178.31630932474
AllCCS[M+H]+175.332859911
AllCCS[M+H-H2O]+172.432859911
AllCCS[M+NH4]+178.132859911
AllCCS[M+Na]+178.932859911
AllCCS[M-H]-179.032859911
AllCCS[M+Na-2H]-179.232859911
AllCCS[M+HCOO]-179.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epietiocholanolone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C2294.0Standard polar33892256
Epietiocholanolone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C2445.5Standard non polar33892256
Epietiocholanolone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C2635.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epietiocholanolone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2=O2570.6Semi standard non polar33892256
Epietiocholanolone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C2576.5Semi standard non polar33892256
Epietiocholanolone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C2600.9Semi standard non polar33892256
Epietiocholanolone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C2517.3Standard non polar33892256
Epietiocholanolone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC=C2O[Si](C)(C)C2936.0Standard polar33892256
Epietiocholanolone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=O)CC[C@H]4[C@@H]3CC[C@@H]2C12814.7Semi standard non polar33892256
Epietiocholanolone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2849.6Semi standard non polar33892256
Epietiocholanolone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3133.8Semi standard non polar33892256
Epietiocholanolone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2774.2Standard non polar33892256
Epietiocholanolone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3181.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epietiocholanolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epietiocholanolone GC-MS (1 TMS) - 70eV, Positivesplash10-001i-2169000000-bf71d6f9c1a2a4af0d202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epietiocholanolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epietiocholanolone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epietiocholanolone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epietiocholanolone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Epietiocholanolone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-0690000000-3a0cb488894ffd7305322012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epietiocholanolone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a5a-3910000000-0fea9c2b9985a4b5c4fc2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epietiocholanolone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0uxu-6691000000-500e59c2f0eb04cba0d82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epietiocholanolone LC-ESI-qTof , Positive-QTOFsplash10-0gx3-0953000000-85e6abfd3e71f7e303f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epietiocholanolone , positive-QTOFsplash10-0a4j-0920100000-b9aa287b6300cd9902b62017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Positive-QTOFsplash10-00dl-0090000000-fb385ad40b5d4ae1a6d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Positive-QTOFsplash10-00dm-0290000000-6287ec557af150ef07fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Positive-QTOFsplash10-000t-3690000000-da6f3211b1e397dcf1ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Negative-QTOFsplash10-000i-0090000000-03f14a475acfab5558d62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Negative-QTOFsplash10-000i-0090000000-5e4902f7af78201459542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Negative-QTOFsplash10-06xx-2090000000-97cca29f0df7b3cc37142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Positive-QTOFsplash10-0006-0090000000-afb176951034ef62419f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Positive-QTOFsplash10-052e-0930000000-1ed776267953f7acda8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Positive-QTOFsplash10-0a4j-2900000000-1ba60805778f2942bfd72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 10V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 20V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epietiocholanolone 40V, Negative-QTOFsplash10-000i-0090000000-00c0e7de4e528b98df5c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • Kidney
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000017 (0.000011-0.000067) uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Schizophrenia
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022109
KNApSAcK IDNot Available
Chemspider ID216866
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpietiocholanolone
METLIN ID5531
PubChem Compound247732
PDB IDNot Available
ChEBI ID542034
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFajkos, J.; Sanda, V. Steroids. LXVI. 16-Bromo derivatives in the 5b-androstane series. Collection of Czechoslovak Chemical Communications (1962), 27 355-61.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [PubMed:12881455 ]