17alpha,20alpha-Dihydroxypregn-4-en-3-one (BioCAD00000002073)
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Metabolite Card
Formula: C21H32O3 (332.2351)
SMILES: [H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Synonyms [en]
(20S)-17,20-dihydroxypregn-4-en-3-one; 17alpha,20alpha-Dihydroxypregn-4-en-3-one; 17Α,20α-dihydroxypregn-4-en-3-one; 17 alpha, 20 alpha-OHP; 4-Pregnen-17alpha, 20alpha-diol-3-one; 4-Pregnen-17a, 20a-diol-3-one
Last reviewed on 2024-06-28.
Cite this Page
17alpha,20alpha-Dihydroxypregn-4-en-3-one. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000002073). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
17 alpha,20alpha-Dihydroxypregn-4-en-3-one, also known as 17,20 alpha-OHP or 20alpha-dihydroxyprogesterone, is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labour and delivery (PMID:6874891). 17,20 alpha-OHP is known to be a substrate for the enzyme 20alpha-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the following chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in the pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hours prior to parturition, ovarian 20alpha-HSD activity is acutely stimulated. 17,20 alpha-OHP is a biologically weaker progestin. Progestin facilitates estrogen induction of the preovulatory luteinizing hormone (LH) surge. It is known that 17,20 alpha-OHP is increased at midcycle but its importance in regulating LH has not been studied. However, periovulatory levels of 17,20 alpha-OHP do not play a role in modulating the estrogen-induced bioactive LH surge (PMID:2245841).
DBLinks
- CAS Registry Number: 652-69-7
- PubChem CID: 440368
- ChEBI: 16418
- HMDB: HMDB0011653
- LipidMaps: LMST02030183
- KEGG: C04518
- BioCyc: 17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3-
- NCBI MeSH:
- Wikipedia:
Other DBLinks
- CAS Registry Number: 652-69-7
- PubChem: 440368
- ChEBI: ChEBI:16418
- HMDB: HMDB0011653
- LipidMaps: LMST02030183
- KEGG: C04518
- BioCyc: 17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3-
- Metlin: METLIN_57873
Class / Ontology
| ID | EC Number | Name |
|---|---|---|
| KEGG:R03325 | 1.1.1.149 | 17alpha,20alpha-dihydroxypregn-4-en-3-one:NADP+ 20-oxidoreductase |
| Rhea:RHEA:15854 | 1.1.1.149 | (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ => 17α-hydroxyprogesterone + NADH + H+ |
| Rhea:RHEA:15855 | 1.1.1.149 | 17α-hydroxyprogesterone + NADH + H+ => (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ |
| Rhea:RHEA:15856 | 1.1.1.149 | (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NAD+ <=> 17α-hydroxyprogesterone + NADH + H+ |
| Rhea:RHEA:15858 | 1.1.1.149 | (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ => 17α-hydroxyprogesterone + NADPH + H+ |
| Rhea:RHEA:15859 | 1.1.1.149 | 17α-hydroxyprogesterone + NADPH + H+ => (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ |
| Rhea:RHEA:15860 | 1.1.1.149 | (17R,20S)-17,20-dihydroxypregn-4-en-3-one + NADP+ <=> 17α-hydroxyprogesterone + NADPH + H+ |
| BioCyc:1.1.1.149-RXN | 1.1.1.149 | 17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3- + NAD-P-OR-NOP<=>17-ALPHA-HYDROXYPROGESTERONE + NADH-P-OR-NOP + PROTON |