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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:02 UTC
HMDB IDHMDB0000493
Secondary Accession Numbers
  • HMDB00493
Metabolite Identification
Common Name5alpha-Androstane-3beta,17beta-diol
Description5alpha-Androstane-3beta,17beta-diol, also known as 5-α-androstane-3-β,17β-diol or 3beta,17beta-dihydroxy-5alpha-androstane, 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, 5alpha-androstane-3beta,17beta-diol is considered to be a steroid. Based on a literature review a significant number of articles have been published on 5alpha-Androstane-3beta,17beta-diol.
Structure
Data?1582752134
Synonyms
ValueSource
(3beta,5alpha,17beta)-Androstane-3,17-diolChEBI
3beta,17beta-Dihydroxy-5alpha-androstaneChEBI
5-ALPHA-ANDROSTANE-3-BETA,17BETA-diolChEBI
5alpha-Androstan-3beta,17beta-diolChEBI
(3b,5a,17b)-Androstane-3,17-diolGenerator
(3Β,5α,17β)-androstane-3,17-diolGenerator
3b,17b-Dihydroxy-5a-androstaneGenerator
3Β,17β-dihydroxy-5α-androstaneGenerator
5-a-ANDROSTANE-3-b,17b-diolGenerator
5-Α-androstane-3-β,17β-diolGenerator
5a-Androstan-3b,17b-diolGenerator
5Α-androstan-3β,17β-diolGenerator
5a-Androstane-3b,17b-diolGenerator
5Α-androstane-3β,17β-diolGenerator
3b,17b-AndrostanediolHMDB
3b-AndrostanediolHMDB
3Β-androstanediolHMDB
5alpha-Androstane-3beta,17beta-diolHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional Name(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number571-20-0
SMILES
[H][C@@]12CC[C@H](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/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyCBMYJHIOYJEBSB-YSZCXEEOSA-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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.56ALOGPS
logP3.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m³·mol⁻¹ChemAxon
Polarizability35.56 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]+168.85431661259
DarkChem[M-H]-164.97231661259
AllCCS[M+H]+177.83932859911
AllCCS[M-H]-179.13632859911
DeepCCS[M-2H]-206.06930932474
DeepCCS[M+Na]+180.61830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Androstane-3beta,17beta-diol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C2433.3Standard polar33892256
5alpha-Androstane-3beta,17beta-diol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C2438.1Standard non polar33892256
5alpha-Androstane-3beta,17beta-diol[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C2611.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Androstane-3beta,17beta-diol,1TMS,isomer #1C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]122563.9Semi standard non polar33892256
5alpha-Androstane-3beta,17beta-diol,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O2552.9Semi standard non polar33892256
5alpha-Androstane-3beta,17beta-diol,2TMS,isomer #1C[C@]12CC[C@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C)CC[C@@H]122573.3Semi standard non polar33892256
5alpha-Androstane-3beta,17beta-diol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2857.1Semi standard non polar33892256
5alpha-Androstane-3beta,17beta-diol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]32)C12820.7Semi standard non polar33892256
5alpha-Androstane-3beta,17beta-diol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13133.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-0290000000-f3f7878ea287111516862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2226900000-73765a85fad7c004bde82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3beta,17beta-diol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0feb-0910000000-95c33219e21fca1431b42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-006t-9621000000-2bf4147f35ce4e2b858a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0aos-9851000000-65b418ed0598e7d185522012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Positive-QTOFsplash10-004l-0090000000-22d60c19836ea8b4c2912017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Positive-QTOFsplash10-056r-0390000000-edb0fb77b27575b4b7292017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Positive-QTOFsplash10-00mk-2980000000-cd6eafa93f3164ed780a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Negative-QTOFsplash10-0006-0090000000-bc689c3cdfdf044c011e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Negative-QTOFsplash10-006x-0090000000-bfbc140857bbdb62bcff2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Negative-QTOFsplash10-06vm-1290000000-bced1e06a8686f3501af2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Positive-QTOFsplash10-002f-0090000000-36f4d97265b0d994d6282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Positive-QTOFsplash10-052b-3940000000-b87bad8b672cc5fb32b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Positive-QTOFsplash10-0aos-3900000000-0f8ce10c286f165d6e0f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 10V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 20V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3beta,17beta-diol 40V, Negative-QTOFsplash10-000l-0090000000-ac9e93370094e8aebfa12021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000149 (0.000057-0.00025) uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB03882
Phenol Explorer Compound IDNot Available
FooDB IDFDB022073
KNApSAcK IDNot Available
Chemspider ID211834
KEGG Compound IDC12525
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3β-Androstanediol
METLIN ID5479
PubChem Compound242332
PDB IDNot Available
ChEBI ID18329
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMerlani, M. I.; Amiranashvili, L. Sh.; Men'shova, N. I.; Kemertelidze, E. P. Synthesis of 5a-androstan-3b,17b-diol from tigogenin. Chemistry of Natural Compounds (2007), 43(1), 97-99.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Stewart ME, Pochi PE, Strauss JS, Wotiz HH, Clark SJ: In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol. J Endocrinol. 1977 Mar;72(3):385-90. [PubMed:856929 ]
  2. Guerini V, Sau D, Scaccianoce E, Rusmini P, Ciana P, Maggi A, Martini PG, Katzenellenbogen BS, Martini L, Motta M, Poletti A: The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype. Cancer Res. 2005 Jun 15;65(12):5445-53. [PubMed:15958594 ]