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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:50:50 UTC
Update Date2022-03-07 02:51:28 UTC
HMDB IDHMDB0013199
Secondary Accession Numbers
  • HMDB13199
Metabolite Identification
Common Name5-Androstene-3alpha-16beta,17beta-triol
Description5-Androstene-3alpha-16beta,17beta-triol, also known as 5-androstene-3α-16β,17β-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. Based on a literature review a small amount of articles have been published on 5-Androstene-3alpha-16beta,17beta-triol.
Structure
Data?1600362978
Synonyms
ValueSource
5-Androstene-3a-16b,17b-triolGenerator
5-Androstene-3α-16β,17β-triolGenerator
5-Androstene-3alpha-16beta,17beta-triolHMDB
Chemical FormulaC19H30O3
Average Molecular Weight306.446
Monoisotopic Molecular Weight306.219494826
IUPAC Name(1S,2R,5R,10R,11S,13S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,13,14-triol
Traditional Name(1S,2R,5R,10R,11S,13S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,13,14-triol
CAS Registry Number220408-23-1
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+/m1/s1
InChI KeyGUGSXATYPSGVAY-GCXXXECGSA-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
  • 16-hydroxysteroid
  • 16-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
Polarizability35.74 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
DeepCCS[M-2H]-208.20530932474
DeepCCS[M+Na]+182.38330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Androstene-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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@@]21C3060.2Semi standard non polar33892256
5-Androstene-3alpha-16beta,17beta-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-3alpha-16beta,17beta-triol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1O3323.6Semi standard non polar33892256
5-Androstene-3alpha-16beta,17beta-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-3alpha-16beta,17beta-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-3alpha-16beta,17beta-triol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C3612.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol 10V, Positive-QTOFsplash10-0a4r-0089000000-9b686589b3ff478d194e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol 20V, Positive-QTOFsplash10-05g1-0962000000-19f3c0d5ec8146c374212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol 40V, Positive-QTOFsplash10-0002-2930000000-88bac32bf4cdeadf65052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol 10V, Negative-QTOFsplash10-0a4i-0009000000-a47a32e502bdb7f0b4482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol 20V, Negative-QTOFsplash10-0a4i-0049000000-520068843a797c5fce132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Androstene-3alpha-16beta,17beta-triol 40V, Negative-QTOFsplash10-0py0-0097000000-2eb4bc803bec5671cb712021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB029327
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92288779
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.