5beta-Dihydrotestosterone
Basic information
- CAS
571-22-2- Standard SMILES
C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12- InChIKey
NVKAWKQGWWIWPM-MISPCMORSA-N- Molecular formula
- C19H30O2
- Average molar mass
- 290.4 g/mol
- Monoisotopic mass
- 290.2245802
Overview
5beta-dihydrotestosterone is a 17beta-hydroxyandrostan-3-one that has beta- configuration at position 5. It is a metabolite of testosterone. It has a role as a vasodilator agent, an androgen, a mouse metabolite and a human metabolite. It is a 3-oxo-5beta-steroid and a 17beta-hydroxyandrostan-3-one.
Names & identifiers
- Preferred name
- 5beta-Dihydrotestosterone
- IUPAC
- (5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
- English name
- 5beta-Androstan-17beta-ol-3-one
- Molecular formula
- C19H30O2
- Molecular weight
- 290.45
Names & synonyms
5beta-Dihydrotestosterone571-22-25beta-Androstan-17beta-ol-3-one5-beta-Dht5-beta-Dihydrotestosterone17beta-Hydroxyetiocholan-3-oneEtiocholan-17-beta-ol-3-one17beta-hydroxy-5beta-androstan-3-one5beta,17beta-Hydroxyandrostan-3-oneEtiocholane-17-beta-ol-3-oneSVX1G0C5VDNSC 15460
Show more names
RMA-5045β-Dihydrotestosteroneetiocholan-17B-ol-3-oneEtiocholan-17β-ol-3-one5β-ANDROSTAN-17β-OL-3-ONEETIOCHOLAM-17BETA-OL-3-ONE5β-Androstane-17β-ol-3-one5b-Androstane-17b-ol-3-one
17-beta-Hydroxy-5-beta-androstan-3-one(5beta,17beta)-17-hydroxyandrostan-3-one(5-beta,17-beta)-17-Hydroxyandrostan-3-one(5beta,8alpha,17beta)-17-hydroxyandrostan-3-one5.beta.-Dihydrotestosterone5beta-Androstan-3-one, 17beta-hydroxy-CHEBI:2150DTXSID0022488
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 458
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
SpringerMaterials PropertiesChemical shift
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 143 °C · 143°C
- Boiling point
- 372.52 °C · 372.52°C (rough estimate)
- Density
- 1.032 · 1.0320 (rough estimate)
- refractive index
- 1.4709 · 1.4709 (estimate)
- solubility
- Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 15.08 · 15.08±0.60(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- BV8054000
- risk_code
- 45-46-61-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-22-36/37/39-45
- Hazard statements
- H360-H350-H332-H302-H312
- Precautionary statements
- P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Metabolite Pathways17-Beta Hydroxysteroid Dehydrogenase III Deficiency
Applications
Uses5b-Androstane-17b-ol-3-one decreases KCI-induced [Ca2+]i increment and may prevent bronchospasm.
Additional notes
DefinitionChEBI: 5beta-dihydrotestosterone is a 17beta-hydroxyandrostan-3-one that has beta- configuration at position 5. It is a metabolite of testosterone. It has a role as an androgen, a mouse metabolite, a vasodilator agent and a human metabolite. It is a 17beta-hydroxyandrostan-3-one and a 3-oxo-5beta-steroid.
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