3-oxoandrost-4-en-17alpha-yl beta-D-glucopyranosiduronic acid
Basic information
- CAS
16996-33-1- Standard SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@H]2O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
NIKZPECGCSUSBV-RWUBDERLSA-N- Molecular formula
- C25H36O8
- Average molar mass
- 464.5 g/mol
- Monoisotopic mass
- 464.2410181
Overview
Epitestosterone 17-O-(beta-D-glucuronide) is a steroid glucosiduronic acid that is epitestosterone in which the hydroxy hydrogen at position 17 has been replaced by a beta-D-glucuronyl residue. It is a beta-D-glucosiduronic acid, a steroid glucosiduronic acid, a 3-oxo steroid and an enone. It is functionally related to an epitestosterone. It is a conjugate acid of an epitestosterone 17-O-(beta-D-glucuronide)(1-).
Names & identifiers
- Preferred name
- 3-oxoandrost-4-en-17alpha-yl beta-D-glucopyranosiduronic acid
- IUPAC
- (2S,3S,4S,5R,6R)-6-[[(8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
- English name
- EPITESTOSTERONE GLUCURONIDE
- Molecular formula
- C25H36O8
- Molecular weight
- 464.55
Names & synonyms
Epitestosterone 17-glucuronideCHEBI:137491DTXSID401363613epitestosterone 17-O-(beta-D-glucuronide)NS0009695717alpha-testosterone 17-O-(beta-D-glucuronide)3-oxoandrost-4-en-17alpha-yl beta-D-glucopyranosiduronic acidb-D-Glucopyranosiduronic acid, (5a,6a)-7,8-didehydro-4,5-epoxy-3-methoxy-17-(methyl-d3)morphinan-6-yl(9CI)NIKZPECGCSUSBV-FVPSFNMHSA-NEPITESTOSTERONE GLUCURONIDEEPI-TESTOSTERONE-17-GLUCURONIDECIS-TESTOSTERONE-17-GLUCURONIDE
Show more names
4-ANDROSTEN-17ALPHA-OL-3-ONE-17-GLUCURONIDE4-ANDROSTEN-17-ALPHA-OL-3-ONE GLUCOSIDURONATEβ-D-Glucopyranosiduronic acid, (17α)-3-oxoandrost-4-en-17-yl
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 855
Experimental & physicochemical properties
Collision Cross Section204.69 Ų [M+H]+
Physicochemical properties
- Boiling point
- 676.963 · 676.963±55.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.37 · 1.370±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 2.821 · 2.821±0.70(predicted)
Chemistry & industry
Applications
UsesEpitestosterone Glucuronide is the glucuronide derivative of Epitesosterone (T155005), a endogenous steroid hormone that has been demonstrated to act at various levels as a weak antiandrogen.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Testosterone 17-glucosiduronic acid is a steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17. It has a role as a human metabolite. It is a 3-oxo steroid, a beta-D-glucosiduronic acid, an enone and a steroid glucosiduronic acid. It is functionally related to a testosterone. It is a conjugate acid of a testosterone 17-O-(beta-D-glucuronide)(1-).
Related reactions
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Compound notes
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