Compound
epitestosterone
The 17-alpha isomer of testosterone, derived from pregnenolone via the delta5-steroid pathway, and via 5-androstene-3-beta,17-alpha-diol. Epitestosterone acts as an antiandrogen in various target tissues. The ratio between testosterone/epitestosterone is used to monitor anabolic drug abuse.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C19H28O2
- Mass
- 288.431 g/mol
- Charge
- 0
- InChIKey
- MUMGGOZAMZWBJJ-KZYORJDKSA-N
- SMILES
- [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](O)CC[C@@]21[H]
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
3 entities
3 entities reached.
What the reference databases state
Chemical structure
- epitestosterone 17-O-(beta-D-glucuronate) has the functional parent epitestosteroneCompoundChEBI CHEBI:136673Inferred only
Statements
4 statements
4 statements · 1 reference database · Subject: epitestosterone · Sources: Rhea
- epitestosterone is converted to epitestosterone 17-O-(beta-D-glucuronate)CompoundRhea RHEA:52568Inferred only
- epitestosterone is metabolised by UGT2A1ProteinRhea RHEA:52568Inferred only
- epitestosterone is metabolised by UGT2B7ProteinRhea RHEA:52568Inferred only
- epitestosterone is a substrate of AKR1D1ProteinRhea RHEA:46652Inferred only
Reactions
2 reactions
epitestosterone+NADPH(4-)+hydronCHEBI:86377+NADP(3-)
Catalysed by AKR1D1
Reaction pageLeft to rightBalanced
Rhea RHEA:46652CC BY 4.0Reference data
epitestosterone+UDP-alpha-D-glucuronateepitestosterone 17-O-(beta-D-glucuronate)+UDP+hydron
Reaction pageLeft to rightBalanced
Rhea RHEA:52568CC BY 4.0Reference data
Other names
4 names
Resolves to: epitestosterone
- Also called
- epi-testosteroneST 19:2;O2
- Systematic name
- 17alpha-hydroxyandrost-4-en-3-one17α-hydroxyandrost-4-en-3-one