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5α-Dihydroprogesterone
Sign in to saveAlso 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.
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 Ų
- 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
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- Chemistry
- See also
- References
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.
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.
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