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Human Metabolome Database Version 3.5

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Showing metabocard for 7a,17-dimethyl-5b-Androstane-3a,17b-diol (HMDB06013)

Record Information
Version 3.5
Creation Date 2007-04-12 14:20:42 -0600
Update Date 2013-02-08 17:14:28 -0700
HMDB ID HMDB06013
Secondary Accession Numbers None
Metabolite Identification
Common Name 7a,17-dimethyl-5b-Androstane-3a,17b-diol
Description 7a,17-dimethyl-5b-Androstane-3a,17b-diol is a urinary metabolite of the anabolic androgenic steroid (AAS) bolasterone. Androgenic anabolic steroids are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. The use of anabolic steroids was banned by the International Olympic Committee for the first time at the Olympic Games in Montreal in 1976. Since that time the misuse of anabolic steroids by athletes has been controlled by analysis of urine of the excreted steroids or their metabolites, or both. (PMID: 10932808 Link_out, 14976846 Link_out, 15042372 Link_out, 15231229 Link_out, 16195040 Link_out, 16292586 Link_out, 1663826 Link_out, 16799097 Link_out, 16888758 Link_out, 16923823 Link_out, 17667636 Link_out, 17723876 Link_out, 17723877 Link_out, 2079979 Link_out, 3308301 Link_out, 8456050 Link_out, 8674183 Link_out, 8725393 Link_out, 9216475 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3a,5b,7a,17b)-7,17-dimethyl-Androstane-3,17-diol
  2. 7a,17a-Dimethyl-5b-androstane-3a,17b-diol
Chemical Formula C21H36O2
Average Molecular Weight 320.5093
Monoisotopic Molecular Weight 320.271530396
IUPAC Name (1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional IUPAC Name (1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number 13611-10-4
SMILES [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier InChI=1S/C21H36O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h13-18,22-23H,5-12H2,1-4H3/t13-,14-,15-,16+,17+,18-,19+,20+,21+/m1/s1
InChI Key ZWQUPIDNCOVROC-HEEAJRSSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Diterpenes
  • Hydroxysteroids
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Tertiary Alcohol
Direct Parent Androgens and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
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
  • 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 0.0022 g/L ALOGPS
LogP 4.23 ALOGPS
LogP 3.77 ChemAxon
LogS -5.16 ALOGPS
pKa (strongest acidic) 18.3 ChemAxon
pKa (strongest basic) -0.47 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 93.82 ChemAxon
Polarizability 38.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • 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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023802
KNApSAcK ID Not Available
Chemspider ID 23254171 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06013 Link_out
Metagene Link HMDB06013 Link_out
METLIN ID Not Available
PubChem Compound 15706076 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available