1.0 2016-09-30 23:25:43 UTC 2020-04-22 15:18:30 UTC BMDB0006763 BMDB06763 20a,22b-Dihydroxycholesterol 20a,22b-Dihydroxycholesterol belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 20a,22b-Dihydroxycholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 20a,22b-Dihydroxycholesterol participates in a number of enzymatic reactions, within cattle. In particular, 20a,22b-Dihydroxycholesterol can be converted into pregnenolone and 4-methylpentanal through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 20a,22b-Dihydroxycholesterol can be biosynthesized from 22b-hydroxycholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 20a,22b-dihydroxycholesterol is involved in the metabolic pathway called the steroidogenesis pathway. 20alpha,22beta-Dihydroxycholesterol C27H46O3 418.6523 418.344695338 (2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol (2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol 15234-55-6 [H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19?,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1 ISBSSBGEYIBVTO-IVMOZYHGSA-N belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Trihydroxy bile acids, alcohols and derivatives 3-hydroxy delta-5-steroids Cholesterols and derivatives Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Secondary alcohols Tertiary alcohols 20-hydroxysteroid 22-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cholestane-skeleton Cholesterol Cholesterol-skeleton Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Tertiary alcohol Trihydroxy bile acid, alcohol, or derivatives Aliphatic homopolycyclic compounds Solid logp 5.08 ALOGPS logs -4.72 ALOGPS logp 4.72 ChemAxon pka_strongest_acidic 13.61 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (2R,3R)-2-[(1S,2R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-6-methylheptane-2,3-diol ChemAxon average_mass 418.6523 ChemAxon mono_mass 418.344695338 ChemAxon smiles [H][C@@]12CC[C@]([H])([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C ChemAxon formula C27H46O3 ChemAxon inchi InChI=1S/C27H46O3/c1-17(2)6-11-24(29)27(5,30)23-10-9-21-20-8-7-18-16-19(28)12-14-25(18,3)22(20)13-15-26(21,23)4/h7,17,19-24,28-30H,6,8-16H2,1-5H3/t19?,20-,21-,22-,23-,24+,25-,26-,27+/m0/s1 ChemAxon inchikey ISBSSBGEYIBVTO-IVMOZYHGSA-N ChemAxon polar_surface_area 60.69 ChemAxon refractivity 123.66 ChemAxon polarizability 51.5 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 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::CMs 10150 Specdb::CMs 39077 Specdb::CMs 172105 Specdb::MsMs 288415 Specdb::MsMs 288416 Specdb::MsMs 288417 Specdb::MsMs 327526 Specdb::MsMs 327527 Specdb::MsMs 327528 Specdb::MsMs 2806709 Specdb::MsMs 2806710 Specdb::MsMs 2806711 Specdb::MsMs 2898207 Specdb::MsMs 2898208 Specdb::MsMs 2898209 C05501 59651624 53477897 FDB024066 190409