Compound: Isopregnanolone
SMILES: O=C([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@H](C[C@@H](O)CC4)CC3)C)CC2)CC1)C)C
InChIKey: AURFZBICLPNKBZ-FZCSVUEKSA-N
Synonyms: Isopregnanolone, 516-55-2, Sepranolone, 5alpha-Pregnan-3beta-ol-20-one, Allopregnan-3beta-ol-20-one, Isoallopregnanolone, 3beta-Hydroxy-5alpha-pregnan-20-one, Sepranolona, 3-beta-Hydroxy-5-alpha-pregnan-20-one, 3P8Z6V53MU, (3beta,5alpha)-3-hydroxypregnan-20-one, NSC-97078, UC1010, UC-1010, CHEBI:11909, U-0949, DTXSID001023710, sepranolonum, RefChem:1087665, DTXCID401508027, Epiallopregnanolone, Alloepipregnanolone, NSC 97078, 3beta-hydroxy-5alpha-pregnane-20-one, Sepranolone [INN], U 0949, CHEMBL2057301, 1-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone, 3-beta-Allopregnanolone, 3.beta.-Hydroxy-5.alpha.-tetrahydroprogesterone, Pregnan-20-one, 3-hydroxy-, (3.beta.,5.alpha.)-, Allopregnan-3.beta.-ol-20-one, 3b-hydroxy-5a-pregnan-20-one, 5-alpha-Dihydropregnenolone, 5a-Dihydropregnenolone, 3.beta.-Hydroxy-5.alpha.-pregnan-20-one, Allopregnan-3?-ol-20-one, EINECS 208-224-2, Allopregnan-3b-ol-20-one, 3?-hydroxy-5?-pregnan-20-one, UNII-3P8Z6V53MU, 5a-Pregnan-3b-ol-20-one, 5.alpha.-Pregnan-3.beta.-ol-20-one, 5.alpha.-Pregnane-3.beta.-ol-20-one, 3b-Allopregnanolone, 5.alpha.-Pregnan-20-one, 3.beta.-hydroxy-, 5alpha-Pregnan-20-one, 3beta-hydroxy-, (3beta,5alpha)-3-Hydroxy-pregnan-20-one, 5-alpha-Pregnan-20-one, 3-beta-hydroxy-, 3.beta.-Allopregnanolone, 3beta-tetrahydroprogesterone, 5.alpha.-Dihydropregnenolone, 5a-Pregnane-3b-ol-20-one, Allopregnan-3|A-ol-20-one, Pregnan-20-one, 3-hydroxy-, (3-beta,5-alpha)-, SCHEMBL598848, orb1299630, orb3141090, Allopregnane-3.beta.-ol-20-one, GLXC-07896, 3b-Hydroxy-5a-tetrahydroprogesterone, 5-alpha-Pregnan-3-beta-ol-20-one, BDBM50388495, LMST02030173, 3b-Hydroxy-5a,17b-pregnan-20-one, AKOS027250789, DB12972, FA67990, MSK174498-100A, UC 1010, AS-82855, SY280714, 3-Deoxo-3b-hydroxy-5a-dihydroprogesterone, HY-113307, CS-0059559, NS00014713, ALLOPREGNAN-3.BETA.-OL-20-ONE [MI], 3-Hydroxypregnan-20-one, (3.beta.,5.alpha.)-, Allopregnanolone Solution in Acetonitrile, 100ug/mL, Q18352362, 1-((3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
Theoretical properties:
molecular_formula: C21H34O2
molecular_weight: 318.5 g/mol
exact_mass: 318.255880323 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 23
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 194.5 °C
Descriptions:
{"pubchem": "3beta-hydroxy-5alpha-pregnan-20-one is a 3-hydroxy-5alpha-pregnan-20-one.", "chebi": null, "chembl": "SEPRANOLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Isopregnanolone, also known as isoallopregnanolone and epiallopregnanolone, as well as sepranolone (INNTooltip International Nonproprietary Name), and as 3\u03b2-hydroxy-5\u03b1-pregnan-20-one or 3\u03b2,5\u03b1-tetrahydroprogesterone (3\u03b2,5\u03b1-THP), is an endogenous neurosteroid and a natural 3\u03b2-epimer of allopregnanolone. It has been reported to act as a subunit-selective negative allosteric modulator of the GABAA receptor, and antagonizes in animals and humans some but not all of the GABAA receptor-mediated effects of allopregnanolone, such as anesthesia, sedation, and reduced saccadic eye movements, but not learning impairment. Isopregnanolone has no hormonal effects and appears to have no effect on the GABAA receptor by itself; it selectively antagonizes allopregnanolone and does not affect the effects of other types of GABAA receptor positive allosteric modulators such as benzodiazepines or barbiturates.\nIsopregnanolone is synthesized from progesterone in the body by the actions of the enzymes 5\u03b1-reductase and 3\u03b2-hydroxysteroid dehydrogenase (with 5\u03b1-dihydroprogesterone as the intermediate in this two-step transformation) and can be reversibly metabolized into allopregnanolone by the enzyme 3\u03b1-hydroxysteroid dehydrogenase. Levels of isopregnanolone, progesterone, and allopregnanolone are highly correlated across the menstrual cycle and throughout pregnancy. The concentrations of isopregnanolone are significantly less than those of progesterone and allopregnanolone; about half of those of allopregnanolone, to be precise. Isopregnanolone has a relatively long serum elimination half-life of 14 hours in humans.\nIsopregnanolone (developmental code name UC-1010) is under development for the treatment of premenstrual dysphoric disorder. As of 2017, it is in phase II clinical trials for this indication.\n\n"}