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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000523
Secondary Accession Numbers
  • HMDB00523
Metabolite Identification
Common Name5-Androstene-3b,16b,17a-triol
Description5-Androstene-3b,16b,17a-triol 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, 5-androstene-3b,16b,17a-triol is considered to be a steroid. Based on a literature review a small amount of articles have been published on 5-Androstene-3b,16b,17a-triol.
Structure
Data?1582752137
SynonymsNot Available
Chemical FormulaC19H30O3
Average Molecular Weight306.4397
Monoisotopic Molecular Weight306.219494826
IUPAC Name(1S,2R,5S,10R,11S,13S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol
Traditional Name5-androstene-3b,16b,17a-triol
CAS Registry Number25126-70-9
SMILES
[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16-,17+,18-,19-/m0/s1
InChI KeyGUGSXATYPSGVAY-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
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 16-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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 Solubility0.19 g/LALOGPS
logP2.17ALOGPS
logP1.72ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.84 m³·mol⁻¹ChemAxon
Polarizability35.8 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]+172.90331661259
DarkChem[M-H]-168.8731661259
AllCCS[M+H]+179.42332859911
AllCCS[M-H]-180.78332859911
DeepCCS[M-2H]-207.55830932474
DeepCCS[M+Na]+181.60930932474
AllCCS[M+H]+179.432859911
AllCCS[M+H-H2O]+176.532859911
AllCCS[M+NH4]+182.132859911
AllCCS[M+Na]+182.932859911
AllCCS[M-H]-180.832859911
AllCCS[M+Na-2H]-181.032859911
AllCCS[M+HCOO]-181.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Androstene-3b,16b,17a-triol[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2795.2Standard polar33892256
5-Androstene-3b,16b,17a-triol[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2693.2Standard non polar33892256
5-Androstene-3b,16b,17a-triol[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C2815.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Androstene-3b,16b,17a-triol,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)[C@H]2O2749.7Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1C[C@H](O)[C@H]2O[Si](C)(C)C2766.9Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O)[C@H]2O2736.0Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)[C@H]2O2795.8Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C2840.8Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O)[C@H]2O[Si](C)(C)C2820.8Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C2832.6Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@@H]1O3041.1Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C3060.2Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@H](O)[C@@H](O)[C@@]4(C)CC[C@@H]32)C13032.2Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@]4(C)CC[C@@H]32)C13338.3Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@@H]1O[Si](C)(C)C(C)(C)C3399.5Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13368.4Semi standard non polar33892256
5-Androstene-3b,16b,17a-triol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]32)C13617.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0090000000-92a740780401e8faa5872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-1013980000-19f683f12fe72ee4fbe82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3b,16b,17a-triol GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 10V, Positive-QTOFsplash10-052r-0094000000-fd24b7644323a9a8e64a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 20V, Positive-QTOFsplash10-0079-0191000000-ee6440f64ac2ade69d3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 40V, Positive-QTOFsplash10-022c-3690000000-93ef29ee24b8ab4da9862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 10V, Negative-QTOFsplash10-0a4i-0039000000-575557def76fdbc5c6132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 20V, Negative-QTOFsplash10-0a4r-0089000000-bde6dc328afc8b9ae9c82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 40V, Negative-QTOFsplash10-059i-0090000000-88f0d959751e79a1e3822017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 10V, Negative-QTOFsplash10-0a4i-0009000000-a47a32e502bdb7f0b4482021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 20V, Negative-QTOFsplash10-0a4i-0049000000-520068843a797c5fce132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 40V, Negative-QTOFsplash10-0py0-0097000000-2eb4bc803bec5671cb712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 10V, Positive-QTOFsplash10-0a4r-0089000000-9b686589b3ff478d194e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 20V, Positive-QTOFsplash10-05g1-0962000000-19f3c0d5ec8146c374212021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3b,16b,17a-triol 40V, Positive-QTOFsplash10-0002-2930000000-88bac32bf4cdeadf65052021-09-23Wishart 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 IDFDB022091
KNApSAcK IDNot Available
Chemspider ID13628101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5508
PubChem Compound21252251
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHuffman, Max N.; Lott, Mary Harriett. Steric structure of estriol and related steroids. Journal of the American Chemical Society (1947), 69 1835.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Laatikainen T: Identification of C19O3 steroids in the mono- and disulfate fractions of human bile. Steroids. 1970 Jan;15(1):139-50. [PubMed:5410667 ]
  2. Begue RJ, Desgres J, Padieu P, Gustafsson JA: Method of analysis of urinary steroids of human pregnancy by GLC and GC-MS of sephadex LH-20 chromatographic fractions. J Chromatogr Sci. 1974 Dec;12(12):763-6. [PubMed:4452739 ]
  3. Shackleton CH, Gustafsson JA: Steroids in newborns and infants identification by combined gas chromatography-mass spectrometry of the major steroids excreted by a newborn chimpanzee (Pan troglodytes). Steroids. 1971 Aug;18(2):175-86. [PubMed:5126818 ]