| Common Name |
Dihydroandrosterone
| Description |
Dihydroandrosterone is a major metabolite of testosterone. Dihydroandrosterone is the main steroid produced by the immature ovary; at puberty the synthesis of steroids shifts toward 4-ene-3-oxo steroids. testosterone 5a-reduced metabolites, including dihydrotestosterone are produced in the anterior pituitary and the central nervous system. Anabolic androgen steroid (AAS) are one of primary performance-enhancing substances abused by athletes. To defeat doping controls, athletes changed to take endogenous androgens from the application of synthetic AAS. testosterone was one candidate of endogenous androgens abused in sports. testosterone and its relevant steroids in urine is detected and monitored with GC/MS. The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. (PMID: 17112575 , 6243214 , 491593 , 491592 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(3alpha,5alpha,17beta)-Androstane-3,17-diolChEBI
3alpha,17beta-Dihydroxy-5alpha-androstaneChEBI
HombreolChEBI
(3a,5a,17b)-Androstane-3,17-diolGenerator
(3α,5α,17β)-androstane-3,17-diolGenerator
3a,17b-Dihydroxy-5a-androstaneGenerator
3α,17β-dihydroxy-5α-androstaneGenerator
AdiolHMDB
Etiocholane-3a,17b-diolHMDB
3a,5a-TetrahydrotestosteroneHMDB
5a-Androstane-3a,17b-diolHMDB
5alpha-Androstane-3alpha,17beta-androstanediolHMDB
5alpha-Androstane-3alpha,17beta-diolHMDB
Androstane-3a,17b-diolHMDB
Etiocholane-3alpha,17beta-diolHMDB
| Chemical Formlia |
C19H32O2
| Average Molecliar Weight |
292.4562
| Monoisotopic Molecliar Weight |
292.240230268
| IUPAC Name |
(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
| Traditional Name |
5α-androstane-3α,17β-diol
| CAS Registry Number |
1852-53-5
| 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-KHOSGYARSA-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-alpha-hydroxysteroids
17-hydroxysteroids
Secondary alcohols
Cyclic alcohols and derivatives
Hydrocarbon derivatives
| Substituents |
Androgen-skeleton
17-hydroxysteroid
3-alpha-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 |
androstane-3alpha,17beta-diol (CHEBI:36713 )
C19 steroids (androgens) and derivatives (LMST02020052 )
| 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 Point219 – 221 °CNot 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
Polarizability35.39 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| 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 |
Skin
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.000475 (0.000352-0.000548) uMAdlit (>18 years old)MaleNormal
17716701
details
|
| 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 |
FDB022114
| KNApSAcK ID |
Not Available
| Chemspider ID |
15039
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00554
| Metagene Link |
HMDB00554
| METLIN ID |
5538
| PubChem Compound |
15818
| PDB ID |
Not Available
| ChEBI ID |
36713
Product: 11-oxo-mogroside V
References |
| Synthesis Reference |
Kieslich, Klaus. 5a-Androstane-3a,17b-diol. Ger. Offen. (1980), 6 pp. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Deslypere JP, Vermeulen A: Aging and tissue androgens. J Clin Endocrinol Metab. 1981 Aug;53(2):430-4. [PubMed:7251820 ]
- Rittmaster RS, Zwicker H, Thompson DL, Konok G, Norman RW: Androstanediol glucuronide production in human liver, prostate, and skin. Evidence for the importance of the liver in 5 alpha-reduced androgen metabolism. J Clin Endocrinol Metab. 1993 Apr;76(4):977-82. [PubMed:8473413 ]
- Frye CA: Some rewarding effects of androgens may be mediated by actions of its 5alpha-reduced metabolite 3alpha-androstanediol. Pharmacol Biochem Behav. 2007 Feb;86(2):354-67. Epub 2006 Nov 15. [PubMed:17112575 ]
- Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism. I–In the hypothalamus and in the anterior pituitary. J Steroid Biochem. 1979 Jul;11(1A):215-9. [PubMed:491592 ]
- Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism–II. In the ventral prostate and in the seminal vesicles. J Steroid Biochem. 1979 Jul;11(1A):221-5. [PubMed:491593 ]
- Eckstein B, Ravid R: Regulation of ovarian 17 beta-hydroxysteroid dehydrogenase activity by gonadotropin. Biochim Biophys Acta. 1980 Jan 17;627(2):165-71. [PubMed:6243214 ]
|
PMID: 12234490