Compound

(20S)-hydroxypregn-4-en-3-one

A biologically active 20-alpha-reduced metabolite of progesterone. It is converted from progesterone to 20-alpha-hydroxypregn-4-en-3-one by the 20-alpha-hydroxysteroid dehydrogenase in the corpus luteum and the placenta.

Definition from MeSH (D004092), National Library of Medicine, read 2026-09-23. NLM revises MeSH; this copy may not reflect its current record.

CHEBI:28453ChEBI

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Structure

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A generated conformer of (20S)-hydroxypregn-4-en-3-one — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound
Formula: C21H32O2
Mass: 316.485 g/mol
Charge: 0
InChIKey: RWBRUCCWZPSBFC-RXRZZTMXSA-N
SMILES: [H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@H](C)O
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

5 entities

5 entities reached.

0 reported hops5 assembled from the scaffold

What the reference databases state

Statements

8 statements

8 statements · 1 reference database · Subject: (20S)-hydroxypregn-4-en-3-one · Sources: Rhea

Order

(20S)-hydroxypregn-4-en-3-one is converted to progesteroneCompoundRhea RHEA:42108Inferred only
progesterone is converted to (20S)-hydroxypregn-4-en-3-oneCompoundRhea RHEA:42108Inferred only
progesterone is converted to (20S)-hydroxypregn-4-en-3-oneCompoundRhea RHEA:42112Inferred only
(20S)-hydroxypregn-4-en-3-one is a substrate of AKR1C1ProteinRhea RHEA:42108Inferred only
(20S)-hydroxypregn-4-en-3-one is a substrate of AKR1C2ProteinRhea RHEA:42108Inferred only
(20S)-hydroxypregn-4-en-3-one is a substrate of AKR1C3ProteinRhea RHEA:42108Inferred only
(20S)-hydroxypregn-4-en-3-one is a substrate of AKR1C4ProteinRhea RHEA:42108Inferred only
(20S)-hydroxypregn-4-en-3-one is a substrate of HSD17B2ProteinRhea RHEA:42108Inferred only

Reactions

2 reactions

(20S)-hydroxypregn-4-en-3-one+NAD(1-)progesterone+NADH(2-)+hydron
Catalysed by AKR1C4 or HSD17B2 or AKR1C3 or AKR1C2 or AKR1C1
Reaction pageDirection not assertedBalanced
Rhea RHEA:42108CC BY 4.0Reference data
(20S)-hydroxypregn-4-en-3-one+NADP(3-)progesterone+NADPH(4-)+hydron
Catalysed by AKR1C4 or AKR1C3 or AKR1C2 or AKR1C1
Reaction pageRight to leftBalanced
Rhea RHEA:42112CC BY 4.0Reference data

Other names

9 names

Resolves to: (20S)-hydroxypregn-4-en-3-one

Also called: (S)-20-Hydroxypregn-4-en-3-one20alpha-dihydroprogesterone20alpha-Hydroxy-4-pregnen-3-one20alpha-Hydroxypregn-4-en-3-one20alpha-Hydroxyprogesterone20α-dihydroprogesteronedihydroprogesteroneST 21:2;O2
Systematic name: (20S)-20-hydroxypregn-4-en-3-one