| Common Name |
5a-Androstane-3b,17b-diol
| Description |
Androstane-3,17-diol is a metabolite of dihydrotestosterone. It doesnt bind androgen receptors, but efficiently binds the estrogen receptor beta and inhibits prostate cancer cell migration through the activation of estrogen receptor beta. (PMID 15958594 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3beta,5alpha,17beta)-Androstane-3,17-diolChEBI
3beta,17beta-Dihydroxy-5alpha-androstaneChEBI
5-ALPHA-ANDROSTANE-3-BETA,17BETA-diolChEBI
5alpha-Androstan-3beta,17beta-diolChEBI
(3b,5a,17b)-Androstane-3,17-diolGenerator
(3β,5α,17β)-androstane-3,17-diolGenerator
3b,17b-Dihydroxy-5a-androstaneGenerator
3β,17β-dihydroxy-5α-androstaneGenerator
5-a-ANDROSTANE-3-b,17b-diolGenerator
5-α-androstane-3-β,17β-diolGenerator
5a-Androstan-3b,17b-diolGenerator
5α-androstan-3β,17β-diolGenerator
3b,17b-AndrostanediolHMDB
5alpha-Androstane-3beta,17beta-diolHMDB
| Chemical Formlia |
C19H32O2
| Average Molecliar Weight |
292.4562
| Monoisotopic Molecliar Weight |
292.240230268
| IUPAC Name |
(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
| Traditional Name |
5-α-androstane-3-β,17β-diol
| CAS Registry Number |
571-20-0
| SMILES |
[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])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-YSZCXEEOSA-N
| Chemical Taxonomy |
| Description |
This compound 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 mascliine characteristics. They also show profound effects on scalp and body hair in humans.
| Kingdom |
Organic compounds
| Super Class |
Lipids and lipid-like moleclies
| Class |
Steroids and steroid derivatives
| Sub Class |
Androstane steroids
| Direct Parent |
Androgens and derivatives
| Alternative Parents |
3-beta-hydroxysteroids
17-hydroxysteroids
Secondary alcohols
Cyclic alcohols and derivatives
Hydrocarbon derivatives
| Substituents |
Androgen-skeleton
17-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound
| Molecliar Framework |
Aliphatic homopolycyclic compounds
| External Descriptors |
3beta-hydroxy steroid (CHEBI:18329 )
17beta-hydroxy steroid (CHEBI:18329 )
androstane-3,17-diol (CHEBI:18329 )
C19 steroids (androgens) and derivatives (C12525 )
C19 steroids (androgens) and derivatives (LMST02020053 )
| Ontology |
| Status |
Detected and 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.019 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m3·mol-1ChemAxon
Polarizability35.52 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0feb-0910000000-95c33219e21fca1431b4View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-006t-9621000000-2bf4147f35ce4e2b858aView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0aos-9851000000-65b418ed0598e7d18552View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane (predicted from logP)
| Biofluid Locations |
Blood
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected but not Quantified Adlit (>18 years old)Female
Normal
22944140
details
BloodDetected and Quantified0.000149 (0.000057-0.00025) uMAdlit (>18 years old)MaleNormal
17716701
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected but not Quantified Adlit (>18 years old)Female
Schizophrenia
22944140
details
| Associated Disorders and Diseases |
| Disease References |
| Schizophrenia |
- Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
| Associated OMIM IDs |
181500 (Schizophrenia)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022073
| KNApSAcK ID |
Not Available
| Chemspider ID |
211834
| KEGG Compound ID |
C12525
| BioCyc ID |
ALPHA-ANDROSTAN-3BETA17BETA-DIOL
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00493
| Metagene Link |
HMDB00493
| METLIN ID |
5479
| PubChem Compound |
242332
| PDB ID |
AOM
| ChEBI ID |
18329
Product: Monepantel
References |
| Synthesis Reference |
Merlani, M. I.; Amiranashvili, L. Sh.; Menshova, N. I.; Kemertelidze, E. P. Synthesis of 5a-androstan-3b,17b-diol from tigogenin. Chemistry of Natural Compounds (2007), 43(1), 97-99. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Stewart ME, Pochi PE, Strauss JS, Wotiz HH, Clark SJ: In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol. J Endocrinol. 1977 Mar;72(3):385-90. [PubMed:856929 ]
- Guerini V, Sau D, Scaccianoce E, Rusmini P, Ciana P, Maggi A, Martini PG, Katzenellenbogen BS, Martini L, Motta M, Poletti A: The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype. Cancer Res. 2005 Jun 15;65(12):5445-53. [PubMed:15958594 ]
|
PMID: 23083067