Human Metabolome Database Version 3.5

Showing metabocard for 5a-Androstane-3a,17a-diol (HMDB00458)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:26:52 -0600
HMDB ID HMDB00458
Secondary Accession Numbers None
Metabolite Identification
Common Name 5a-Androstane-3a,17a-diol
Description 5a-Androstane-3a,17a-diol is an steroid found in feces from pregnant women (PMID 5440628 Link_out), primarily in the monosulfate and disulfate fractions from normal human (PMID 4245755 Link_out), and glucuronide and mono- and disulphate conjugates of neutral steroids in human bile (PMID 5493463 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3a,17a-Dihydroxy-5a-androstane
  2. 5a-Androstane-3a,17a-diol
Chemical Formula C19H32O2
Average Molecular Weight 292.4562
Monoisotopic Molecular Weight 292.240230268
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 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
CAS Registry Number 6165-21-5
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 Key CBMYJHIOYJEBSB-CUZKMJQKSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • C19 steroids (androgens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • androstane-3alpha,17beta-diol(ChEBI)
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct Parent Androgens and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.019 g/L ALOGPS
LogP 3.56 ALOGPS
LogP 3.2 ChemAxon
LogS -4.18 ALOGPS
pKa (strongest acidic) 18.3 ChemAxon
pKa (strongest basic) -0.76 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 84.63 ChemAxon
Polarizability 35.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022056
KNApSAcK ID Not Available
Chemspider ID 8032954 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00458 Link_out
Metagene Link HMDB00458 Link_out
METLIN ID 5446 Link_out
PubChem Compound 9857254 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference McDermott, 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. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out