1.0 2011-09-21 01:45:23 UTC 2020-04-21 18:03:18 UTC FDB028816 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8-en-3beta-ol is a 3-beta-hydroxysterol that is an intermediate in cholesterol biosynthesis. It is a substrate for lanosterol 14alpha-demethylase (CYP51A1) and can be generated from the enzymatic oxidation of 24,25-dihydrolanosteroland and from the enzymatic reduction of 4,4-dimethyl-14alpha-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] 4,4-Dimethyl-14a-hydroxymethyl-5a-cholesta-8-en-3b-ol 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8-en-3 beta-ol 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8-en-3-beta-ol C30H52O2 444.7327 444.396730908 (2S,5S,11S,15R)-11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol (2S,5S,11S,15R)-11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol CC(C)CCCC(C)C1CC[C@@]2(CO)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3 InChI=1S/C30H52O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h20-22,25-26,31-32H,8-19H2,1-7H3/t21?,22?,25?,26-,28+,29+,30+/m0/s1 SJPDNXKPBQHPMZ-XQVXCQOBSA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Triterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aliphatic homopolycyclic compounds 3-beta-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Primary alcohols Secondary alcohols 3-beta-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Primary alcohol Secondary alcohol Steroid Triterpenoid Solid logp 6.77 ALOGPS logs -5.74 ALOGPS solubility 8.18e-04 g/l ALOGPS logp 6.83 ChemAxon pka_strongest_acidic 19.43 ChemAxon pka_strongest_basic -0.53 ChemAxon iupac (2S,5S,11S,15R)-11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol ChemAxon average_mass 444.7327 ChemAxon mono_mass 444.396730908 ChemAxon smiles CC(C)CCCC(C)C1CC[C@@]2(CO)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3 ChemAxon formula C30H52O2 ChemAxon inchi InChI=1S/C30H52O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h20-22,25-26,31-32H,8-19H2,1-7H3/t21?,22?,25?,26-,28+,29+,30+/m0/s1 ChemAxon inchikey SJPDNXKPBQHPMZ-XQVXCQOBSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 135.47 ChemAxon polarizability 56.17 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16596 Specdb::CMs 39840 Specdb::CMs 146188 Specdb::MsMs 302665 Specdb::MsMs 302666 Specdb::MsMs 302667 Specdb::MsMs 345445 Specdb::MsMs 345446 Specdb::MsMs 345447 Specdb::MsMs 2457407 Specdb::MsMs 2457408 Specdb::MsMs 2457409 Specdb::MsMs 2481787 Specdb::MsMs 2481788 Specdb::MsMs 2481789 HMDB12160 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