Showing metabocard for 5a-Androstane-3b,17b-diol (BMDB0000493)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:33 UTC
Update Date2020-04-21 18:14:43 UTC
BMDB IDBMDB0000493
Secondary Accession Numbers
  • BMDB00493
Metabolite Identification
Common Name5a-Androstane-3b,17b-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
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gj-0290000000-f3f7878ea28711151686View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2226900000-73765a85fad7c004bde8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0feb-0910000000-95c33219e21fca1431b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006t-9621000000-2bf4147f35ce4e2b858aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aos-9851000000-65b418ed0598e7d18552View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-22d60c19836ea8b4c291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0390000000-edb0fb77b27575b4b729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-2980000000-cd6eafa93f3164ed780aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-bc689c3cdfdf044c011eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0090000000-bfbc140857bbdb62bcffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vm-1290000000-bced1e06a8686f3501afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0090000000-36f4d97265b0d994d628View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-3940000000-b87bad8b672cc5fb32b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aos-3900000000-0f8ce10c286f165d6e0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-11452f48ce72555f1f28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-11452f48ce72555f1f28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-0090000000-ac9e93370094e8aebfa1View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000493
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
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 ReferencesNot Available