5α-Dihydroprogesterone

Also known as 5alpha-dihydroprogesterone, 5α-pregnane-3,20-dione, allopregnanedione

5α-Dihydroprogesterone (5α-DHP, allopregnanedione, or 5α-pregnane-3,20-dione) is an endogenous progestogen and neurosteroid that is synthesized from progesterone. It is also an intermediate in the synthesis of allopregnanolone and isopregnanolone from progesterone.

In the Vinony graph

Vinony's link graph records 1,291 inbound references to 5α-Dihydroprogesterone, and connects out to androstenedione, picrotoxin and androstenediol.

It sits within the topics 5α-Pregnanes, Chembox image size set and Diketones.

Vinony links it to 8 Wikipedia language editions.

Chemical data

Formula: C21H32O2
Molecular weight: 316.5 g/mol
IUPAC name: (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
InChIKey: XMRPGKVKISIQBV-BJMCWZGWSA-N
XLogP: 4.4
Polar surface area: 34.1 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

151 papers

Brexanolone.2006
5α-dihydroprogesterone concentrations and synthesis in non-pregnant mares.The Journal of endocrinology · 2018
Effect of 3α-dihydroprogesterone and 5α-dihydroprogesterone on DCIS cells and possible impact for postmenopausal women.Climacteric : the journal of the International Menopause Society · 2023
5alpha-dihydroprogesterone promotes proliferation and migration of human glioblastoma cells.Steroids · 2020
Aging Is Associated With Lower Neuroactive Steroids and Worsened Outcomes Following Cerebral Ischemia in Male Mice.Endocrinology · 2022

via PubMed

Wikidata facts

Mass: 316.24023

Show 6 more facts

chemical formula: C₂₁H₃₂O₂
canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
isomeric SMILES: [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2
found in taxon: Holarrhena pubescens
Commons category: 5α-Dihydroprogesterone
stereoisomer of: 5β-pregnane-3,20-dione

Sources (4)

via Wikidata · CC0

~3 min read

Encyclopedic overview

3 sections

Contents

Chemistry
See also
References

5α-DHP is metabolized by the aldo-keto reductases (AKRs) AKR1C1, AKR1C2, and AKR1C4 with high catalytic efficiency. AKR1C1 preferentially forms 20α-hydroxy-5α-pregnane-3-one while AKR1C2 preferentially forms allopregnanolone. Similarly AKR1C1 reduces and consequently inactivates allopregnanolone into 5α-pregnane-3α,20α-diol. In contrast to the other AKRs, AKR1C3 has low catalytic efficiency for reduction of 5α-DHP. These AKRs are highly expressed in the human liver and mammary gland but have relatively modest expression in the human brain and uterus.

Excerpted from Wikipedia’s “5α-Dihydroprogesterone” article, available under the CC BY-SA 4.0 licence.