17-Hydroxyandrostane-3-glucuronide
Basic information
- CAS
65535-18-4- Standard SMILES
C[C@]12CCC(O[C@@H]3O[C@@H](C(=O)O)[C@@H](O)[C@@H](O)[C@H]3O)CC1CCC1C2CC[C@@]2(C)C1CC[C@H]2O- InChIKey
GYNWSIBKBBWJJW-ZQMNIGHUSA-N- Molecular formula
- C25H40O8
- Average molar mass
- 468.6 g/mol
- Monoisotopic mass
- 468.27231823
Overview
metabolite of androstanediol; RN given refers to (3alpha,5alpha,17beta)-isomer
Names & identifiers
- Preferred name
- 17-Hydroxyandrostane-3-glucuronide
- IUPAC
- (2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-[[(10S,13S,17R)-17-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid
- English name
- 17-hydroxyandrostane-3-glucuronide
- Molecular formula
- C25H40O8
- Molecular weight
- 468.58
Names & synonyms
Adiol 3-G17-Hydroxyandrostane-3-glucuronideRefChem:90824265535-18-4UN7QBZ76ABUNII-UN7QBZ76ABDTXSID50984129(2R,3S,4R,5R,6R)-3,4,5-trihydroxy-6-[[(10S,13S,17R)-17-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid17-Hydroxyandrostan-3-yl hexopyranosiduronic acid(8xi,9xi)-17alpha-Hydroxy-14xi-androstan-3-yl alpha-L-talopyranosiduronic acidbeta-D-Glucopyranosiduronic acid, (3alpha,5alpha,17beta)-17-hydroxyandrostan-3-ylAndrostane-3α,17β-diol 3-Glucuronide
Show more names
Androstane-3alpha,17beta-diol 3-Glucuronide5α-Androstane-3α, 17β-diol-3-O-β-glucuronic acidβ-D-Glucopyranosiduronic acid, (3α,5α,17β)-17-hydroxyandrostan-3-yl
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 137 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 761
Physicochemical properties
- Boiling point
- 656.286 · 656.286±55.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.348 · 1.348±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 2.822 · 2.822±0.70(predicted)
- FDA UNII
- 7 QBZ76AB · UN7QBZ76AB
Chemistry & industry
Applications
UsesAndrostane-3α,17β-diol 3-Glucuronide is a derivative of Androsterone β-D-Glucuronide (A637605), which is one of the major circulating C19-steroid metabolites in humans. Exaggerated Androsterone (A637535) metabolism is observed in hyper-androgenic as well as in some normo-androgenic women with acne and androsterone glucuronide could be a marker in differentiating acne and hirsutism in hyperandrogenic women.
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Compound notes
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