Compound: 5-alpha-Pregnane-3,20-dione
SMILES: O=C1CC2C(C3C(C4C(C(C(=O)C)CC4)(C)CC3)CC2)(C)CC1
InChIKey: XMRPGKVKISIQBV-UHFFFAOYSA-N
Synonyms: 5-alpha-Pregnane-3,20-dione, 17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one, Pregnane 3,20 dione, 5.beta.-Pregnane-3,20-dione, NCIOpen2_008972, SCHEMBL14076094, ALBB-025011, 5-BETA-PREGNANE-3,20-DIONE, AKOS015998290, NS00014749, NS00079760
Theoretical properties:
molecular_formula: C21H32O2
molecular_weight: 316.5 g/mol
exact_mass: 316.240230259 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 34.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": null, "chebi": "A C<small><sub>21</sub></small>-steroid hormone that is 5\u03b1-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone.", "chembl": null, "wikipedia": "5\u03b1-Dihydroprogesterone (5\u03b1-DHP, allopregnanedione, or 5\u03b1-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.\n5\u03b1-DHP is metabolized by the aldo-keto reductases (AKRs) AKR1C1, AKR1C2, and AKR1C4 with high catalytic efficiency. AKR1C1 preferentially forms 20\u03b1-hydroxy-5\u03b1-pregnane-3-one while AKR1C2 preferentially forms allopregnanolone. Similarly AKR1C1 reduces and consequently inactivates allopregnanolone into 5\u03b1-pregnane-3\u03b1,20\u03b1-diol. In contrast to the other AKRs, AKR1C3 has low catalytic efficiency for reduction of 5\u03b1-DHP. These AKRs are highly expressed in the human liver and mammary gland but have relatively modest expression in the human brain and uterus.\n5\u03b1-DHP is an agonist of the progesterone receptor and a positive allosteric modulator of the GABAA receptor (albeit with an affinity for this receptor that is regarded as relatively low (in comparison to 3\u03b1-hydroxylated progesterone metabolites such as allopregnanolone and pregnanolone)). It has also been found to act as a negative allosteric modulator of the GABAA-rho receptor. The steroid has been found to possess 82% of the affinity of progesterone for the progesterone receptor in rhesus monkey uterus. 5\u03b1-Dihydroprogesterone has been said to possess about 33% of the relative progestogenic potency of progesterone. In addition, it is a weak agonist of the pregnane X receptor (PXR) (EC50 >10,000 \u03bcM), with approximately six-fold lower potency relative to its 5\u03b2-isomer, 5\u03b2-dihydroprogesterone.\nAllopregnanolone is transformed back into 5\u03b1-DHP by 3\u03b1-hydroxysteroid oxidoreductase, and conversion of allopregnanolone into 5\u03b1-DHP is responsible for the progestogenic activity of allopregnanolone. 5\u03b1-DHP, via the progesterone receptor, and allopregnanolone, via the GABAA receptor, act together to induce lordosis in animals. A study found that 41% of allopregnanolone that was administered via injection was transformed into 5\u03b1-DHP in the rat brain.\nLevels of 5\u03b1-DHP have been quantified."}