1.0 2011-09-21 01:45:31 UTC 2015-07-21 06:59:32 UTC FDB028820 4alpha-Carboxy-5alpha-cholesta-8-en-3beta-ol 4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis II (via 24,25-dihydrolanosterol). It is a substrate for NAD(P)-dependent steroid dehydrogenase (H105E3) and it can be generated from the enzymatic carboxylation of 5alpha-cholesta-8-en-3-one. It is also a substrate for C-4 methyl sterol oxidase (SC4MOL) and can be generated from the enzymatic oxidation of 4alpha-formyl-5alpha-cholesta-8-en-3beta-ol. The sequence of reactions and the types of intermediates in cholesterol biosynthesis may vary. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates. These intermediates, with or without a double bond in the hydrocarbon side chain, can serve as substrates for the other enzymes in the pathway. [HMDB] 4a-carboxy-5a-cholesta-8-en-3b-ol 4a-carboxy-5a-cholesta-8-en-3beta-ol 4alpha-carboxy-5alpha-cholesta-8-en-3b-ol C28H46O3 430.663 430.344695338 (2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid (2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1 RODBXVVNKJCWQR-KLZNZPMLSA-N belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Cholestane steroids Aliphatic homopolycyclic compounds 3-beta-hydroxysteroids 4-carboxy steroids Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 15-hydroxysteroid 3-beta-hydroxysteroid 3-hydroxysteroid 4-carboxy steroid Alcohol Aliphatic homopolycyclic compound Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Cholesterol-skeleton Cyclic alcohol Hydrocarbon derivative Hydroxy acid Hydroxysteroid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Steroid acid Solid logp 6.20 ALOGPS logs -5.16 ALOGPS solubility 2.98e-03 g/l ALOGPS logp 6.45 ChemAxon pka_strongest_acidic 4.6 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (2S,5S,6S,15R)-5-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carboxylic acid ChemAxon average_mass 430.663 ChemAxon mono_mass 430.344695338 ChemAxon smiles CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@H](C1CC3)C(O)=O ChemAxon formula C28H46O3 ChemAxon inchi InChI=1S/C28H46O3/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(26(30)31)24(29)14-16-28(23,5)22(19)13-15-27(20,21)4/h17-18,20-21,23-25,29H,6-16H2,1-5H3,(H,30,31)/t18?,20?,21?,23?,24-,25-,27+,28+/m0/s1 ChemAxon inchikey RODBXVVNKJCWQR-KLZNZPMLSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 126.44 ChemAxon polarizability 53.16 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18512 Specdb::CMs 39844 Specdb::CMs 134111 Specdb::CMs 141845 Specdb::MsMs 307030 Specdb::MsMs 307031 Specdb::MsMs 307032 Specdb::MsMs 350863 Specdb::MsMs 350864 Specdb::MsMs 350865 Specdb::MsMs 2715523 Specdb::MsMs 2715524 Specdb::MsMs 2715525 Specdb::MsMs 2966520 Specdb::MsMs 2966521 Specdb::MsMs 2966522 HMDB12166 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823