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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:02 UTC
HMDB IDHMDB0000458
Secondary Accession Numbers
  • HMDB00458
Metabolite Identification
Common Name5alpha-Androstane-3alpha,17alpha-diol
Description5alpha-Androstane-3alpha,17a-diol belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. 5alpha-Androstane-3alpha,17a-diol is a steroid found in feces from pregnant women (PMID: 5440628 ), the monosulfate and disulfate fractions from normal human feces (PMID: 4245755 ), and the glucuronide and mono- and disulphate conjugates of neutral steroids in human bile (PMID: 5493463 ).
Structure
Data?1582752132
Synonyms
ValueSource
5a-Androstane-3a,17a-diolGenerator
5Α-androstane-3α,17α-diolGenerator
3a,17a-Dihydroxy-5a-androstaneHMDB
(3alpha,5alpha,17alpha)-Androstane-3,17-diolHMDB
(3Α,5α,17α)-androstane-3,17-diolHMDB
3alpha,17alpha-Dihydroxy-5alpha-androstaneHMDB
3Α,17α-dihydroxy-5α-androstaneHMDB
5alpha-Androstan-3alpha,17alpha-diolHMDB
5Α-androstan-3α,17α-diolHMDB
5alpha-Androstane-3alpha,17alpha-diolHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7S,10R,11S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional Name(1S,2S,5R,7S,10R,11S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number6165-21-5
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-CUZKMJQKSA-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-alpha-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
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 Solubility0.019 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
Polarizability35.17 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]+170.57431661259
DarkChem[M-H]-168.04431661259
AllCCS[M+H]+177.23432859911
AllCCS[M-H]-179.13632859911
DeepCCS[M-2H]-207.8130932474
DeepCCS[M+Na]+182.24430932474
AllCCS[M+H]+177.232859911
AllCCS[M+H-H2O]+174.332859911
AllCCS[M+NH4]+180.032859911
AllCCS[M+Na]+180.732859911
AllCCS[M-H]-179.132859911
AllCCS[M+Na-2H]-179.432859911
AllCCS[M+HCOO]-179.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Androstane-3alpha,17alpha-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-3alpha,17alpha-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-3alpha,17alpha-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-3alpha,17alpha-diol,1TMS,isomer #1C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@H]2O[Si](C)(C)C2563.9Semi standard non polar33892256
5alpha-Androstane-3alpha,17alpha-diol,1TMS,isomer #2C[C@]12CC[C@@H](O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@H]2O2552.9Semi standard non polar33892256
5alpha-Androstane-3alpha,17alpha-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]1CC[C@H]2O[Si](C)(C)C2573.3Semi standard non polar33892256
5alpha-Androstane-3alpha,17alpha-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@@]21C2857.1Semi standard non polar33892256
5alpha-Androstane-3alpha,17alpha-diol,1TBDMS,isomer #2CC(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]3CC[C@H]2O)C12820.7Semi standard non polar33892256
5alpha-Androstane-3alpha,17alpha-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]3CC[C@H]2O[Si](C)(C)C(C)(C)C)C13133.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-0290000000-ef7ce05726cbec3a35bd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2227900000-87cd967afbbb2453594f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 10V, Positive-QTOFsplash10-004l-0090000000-ea970ea07cbd199d95ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 20V, Positive-QTOFsplash10-056r-0290000000-241c15d984d5502957c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 40V, Positive-QTOFsplash10-00mk-2790000000-1fb4fb943a8eb42cf30d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 10V, Negative-QTOFsplash10-0006-0090000000-7976b987ec10e61bdb4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 20V, Negative-QTOFsplash10-006x-0090000000-72251dd83cca96a12d442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 40V, Negative-QTOFsplash10-01r5-0190000000-8a798c89a6c57c1531692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 10V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 20V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 40V, Negative-QTOFsplash10-000l-0090000000-ac9e93370094e8aebfa12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 10V, Positive-QTOFsplash10-002f-0090000000-36f4d97265b0d994d6282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 20V, Positive-QTOFsplash10-052b-3940000000-b87bad8b672cc5fb32b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Androstane-3alpha,17alpha-diol 40V, Positive-QTOFsplash10-0aos-3900000000-0f8ce10c286f165d6e0f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022056
KNApSAcK IDNot Available
Chemspider ID8032954
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9857254
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMcDermott, Ian R.; Robinson, Cecil H. Novel synthesis of 5a-androstane-3a,17a-diol. Journal of the Chemical Society, Chemical Communications (1979), (1), 28-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eriksson H, Gustafsson JA, Sjovall J: Excretion of steroid hormones in adults. C19 and C21 steroids in faeces from pregnant women. Eur J Biochem. 1970 Feb;12(3):520-6. [PubMed:5440628 ]
  2. Laatikainen T, Vihko R: Identification of C19O2 and C21O2 steroids in the mono- and disulphate fractions of human faeces. Eur J Biochem. 1970 Apr;13(3):534-8. [PubMed:4245755 ]
  3. Laatikainen T: Quantitative studies on the excretion of glucuronide and mono- and disulphate conjugates of neutral steroids in human bile. Ann Clin Res. 1970 Dec;2(4):338-49. [PubMed:5493463 ]