1.0 2016-09-30 23:25:42 UTC 2020-05-21 16:28:52 UTC BMDB0006762 BMDB06762 17a,21-Dihydroxypreg-nenolone 17alpha,21-Dihydroxypregnenolone, also known as 17alpha,21-dihydroxypregnenolone, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, 17alpha,21-dihydroxypregnenolone is considered to be a steroid lipid molecule. 17alpha,21-Dihydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 17alpha,21-Dihydroxypregnenolone exists in all living organisms, ranging from bacteria to humans. 17alpha,21-Dihydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 17alpha,21-Dihydroxypregnenolone can be biosynthesized from cortexolone; which is mediated by the enzyme 3-beta-HSD 1. In addition, 17alpha,21-Dihydroxypregnenolone can be biosynthesized from 17a-hydroxypregnenolone; which is catalyzed by the enzyme steroid 21-hydroxylase. In cattle, 17alpha,21-dihydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway. 17a,21-Dihydroxypregnenolone 17Α,21-dihydroxypregnenolone 17alpha,21-Dihydroxypreg-nenolone 17, 21-Dihydroxypregnenolone 3Β,17α,21-trihydroxypregnenone 3beta,17alpha,21-Trihydroxypregnenone 17,21-Dihydroxypregnenolone 3Β,17,21-trihydroxy-pregn-5-en-20-one 3beta,17,21-Trihydroxy-pregn-5-en-20-one (3Β)-3,17,21-trihydroxypregn-5-en-20-one (3beta)-3,17,21-Trihydroxypregn-5-en-20-one 3Β,17α,21-trihydroxypregn-5-en-20-one 3beta,17alpha,21-Trihydroxypregn-5-en-20-one 17alpha,21-Dihydroxypregnenolone C21H32O4 348.4764 348.230059512 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethanone 1167-48-2 [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1 JNHJGXQUDOYJAK-IYRCEVNGSA-N belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Hydroxysteroids 21-hydroxysteroids 17-hydroxysteroids 20-oxosteroids 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Alpha-hydroxy ketones Cyclic alcohols and derivatives Delta-5-steroids Gluco/mineralocorticoids, progestogins and derivatives Hydrocarbon derivatives Organic oxides Primary alcohols Secondary alcohols Tertiary alcohols 17-hydroxysteroid 20-oxosteroid 21-hydroxysteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Alpha-hydroxy ketone Carbonyl group Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Pregnane-skeleton Primary alcohol Progestogin-skeleton Secondary alcohol Tertiary alcohol Aliphatic homopolycyclic compounds 17alpha-hydroxy steroid 21-hydroxy steroid 3beta-hydroxy steroid C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives Solid logp 2.60 ALOGPS logs -3.79 ALOGPS logp 2.02 ChemAxon pka_strongest_acidic 12.59 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-hydroxyethan-1-one ChemAxon average_mass 348.4764 ChemAxon mono_mass 348.230059512 ChemAxon smiles [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C ChemAxon formula C21H32O4 ChemAxon inchi InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1 ChemAxon inchikey JNHJGXQUDOYJAK-IYRCEVNGSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 96.86 ChemAxon polarizability 39.63 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Steroidogenesis SMP0087238 Specdb::MsMs 300802 Specdb::MsMs 300803 Specdb::MsMs 300804 Specdb::MsMs 343168 Specdb::MsMs 343169 Specdb::MsMs 343170 Specdb::MsMs 2315396 Specdb::MsMs 2315397 Specdb::MsMs 2315398 Specdb::MsMs 2620595 Specdb::MsMs 2620596 Specdb::MsMs 2620597 Specdb::CMs 15706 Specdb::CMs 39076 Specdb::CMs 164621 FDB024065 167253 192735 C05487 27832 BMDBP00010 Cytochrome P450 11B1, mitochondrial P15150 CYP11B1 Enzyme