1.0 2010-04-08 22:10:21 UTC 2019-11-26 03:07:35 UTC FDB012781 7,8-Didehydrodesmosterol Constituent of pig tissues and bakers yeast (Saccharomyces cerevisiae) 7-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100% prevalent. (PMID: 15862627, 17197219). 7,8-Didehydrodesmosterol is found in animal foods. (3beta)-cholesta-5,7,24-trien-3-ol 24-Dehydroprovitamin D3 7-dehydrodesmosterol 7,8-Didehydrodesmosterol Cholesta-5,7,24-trien-3-ol, (3beta)- Cholesta-5,7,24-trien-3b-ol Cholesta-5,7,24-trien-3beta-ol Cholesta-5,7,24-trien-3β-ol Cholesta-5,7,24-triene-3b-ol Cholesta-5,7,24-triene-3beta-ol Cholesta-5,7,24-triene-3β-ol C27H42O 382.6218 382.323565966 2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol 2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol 1715-86-2 CC(CCC=C(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3 RUSSPKPUXDSHNC-UHFFFAOYSA-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-hydroxy delta-5-steroids 3-hydroxy delta-7-steroids Cyclic alcohols and derivatives Delta-5-steroids Delta-7-steroids Hydrocarbon derivatives Secondary alcohols 3-hydroxy-delta-5-steroid 3-hydroxy-delta-7-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cholesterol Cholesterol-skeleton Cyclic alcohol Delta-5-steroid Delta-7-steroid Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol a 3-&beta;-hydroxysterol Solid logp 7.46 ALOGPS logs -5.78 ALOGPS solubility 6.40e-04 g/l ALOGPS melting_point Mp 104-107° logp 6.3 ChemAxon pka_strongest_acidic 18.27 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol ChemAxon average_mass 382.6218 ChemAxon mono_mass 382.323565966 ChemAxon smiles CC(CCC=C(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C ChemAxon formula C27H42O ChemAxon inchi InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3 ChemAxon inchikey RUSSPKPUXDSHNC-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 122.32 ChemAxon polarizability 47.71 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Steroid Biosynthesis SMP00023 map00100 Specdb::EiMs 2069 Specdb::CMs 1090225 Specdb::MsMs 90549 Specdb::MsMs 90550 Specdb::MsMs 90551 Specdb::MsMs 153729 Specdb::MsMs 153730 Specdb::MsMs 153731 HMDB03896 27910 #<Reference:0x000055ce30662930> #<Reference:0x000055ce30662778>