| Common Name |
3a,17a-Dihydroxy-5b-androstane
| Description |
The unspecified form of the steroid, normally a major metabolite of testosterone with androgenic activity. It has been implicated as a regliator of gonadotropin secretion.3a,17a-Dihydroxy-5b-androstane is a metabolite of natural androgens (testosterone, epitestosterone, dihydrotestosterone, and dehydroepiandrosterone) present in small amount in the urine of normal individuals (PMID 9381514 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
3 alpha,5 beta,7 alpha-3,7-Dihydroxyandrostan-17-oneHMDB
5b-Androstane-3a,17a-diolHMDB
3,7-DHARN-17-oneMeSH
3,7-Dihydroxyandrostan-17-one, (3beta,5beta,7beta)-isomerMeSH
3,7-Dihydroxyandrostan-17-one, (3beta,5alpha,7alpha)-isomerMeSH
3,7-Dihydroxyandrostan-17-oneMeSH
3,7-Dihydroxyandrostan-17-one, (3beta,5alpha,7beta)-isomerMeSH
3 alpha,7 alpha-5 beta-3,7-Dihydroxyandrostan-17-oneMeSH
| Chemical Formlia |
C19H32O2
| Average Molecliar Weight |
292.4562
| Monoisotopic Molecliar Weight |
292.240230268
| IUPAC Name |
(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
| Traditional Name |
(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
| CAS Registry Number |
5856-10-0
| SMILES |
C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@H]2O
| 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+/m1/s1
| InChI Key |
CBMYJHIOYJEBSB-CRQQDORFSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected but 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 Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
Polarizability35.28 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
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
| 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 |
FDB022001
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
C07632
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00383
| Metagene Link |
HMDB00383
| METLIN ID |
5372
| PubChem Compound |
53477690
| PDB ID |
Not Available
| ChEBI ID |
27727
Product: ARA290
References |
| Synthesis Reference |
Miller, A. M.; Dorfman, Ralph I. Metabolism of the steroid hormones: Isolation of etiocholane-3(a),17(a)-diol from human urine. Endocrinology (1948), 42 174-5. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Uotila P, Hartiala J, Nienstedt W: The metabolism of testosterone by human, rabbit and rat kidney. Int J Biochem. 1980;12(3):345-51. [PubMed:7418937 ]
- 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 ]
- Shackleton CH, Roitman E, Phillips A, Chang T: Androstanediol and 5-androstenediol profiling for detecting exogenously administered dihydrotestosterone, epitestosterone, and dehydroepiandrosterone: potential use in gas chromatography isotope ratio mass spectrometry. Steroids. 1997 Oct;62(10):665-73. [PubMed:9381514 ]
- Peng TC, Munson PL: The isolation of 5-beta-androstane-3-alpha,17-alpha-diol from normal human urine. Steroids. 1968 Feb;11(2):105-12. [PubMed:5636704 ]
|
PMID: 26615780