1.0 2011-09-21 00:13:05 UTC 2015-07-21 06:57:10 UTC FDB022378 25-Azacholesterol 25-Azacholesterol has potent hypocholesterolemic activity. (PMID 14287266) It specifically inhibits cholesterol side-chain cleavage resulting in a decrease in steroid hormone production (PMID 5165491). Azasteroids may be membrane effectors which, in the case of mitochondria, lead to changes in adenosine triphosphate levels and(or) dehydrogenase activity. Their effects on sterol metabolism, therefore, may be of secondary consideration. (PMID 994744) 25-azacholesterol can induce a myotonic state in muscles. (PMID 5009506) [HMDB] (3beta)-24-(dimethylamino)-chol-5-en-3-ol 24-(dimethylamino)chol-5-en-3beta-ol 25-azacholesterol C26H45NO 387.6416 387.350115067 (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-(dimethylamino)pentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol 25-azacholesterol 1973-61-1 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C InChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1 RZPPEFJMRVRCDD-XSLNCIIRSA-N belongs to the class of organic compounds known as 25-azasteroids and derivatives. These are azasteroids where the carbon atom at position 25 is replaced by a nitrogen atom. 25-azasteroids and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Azasteroids and derivatives Aliphatic homopolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Organopnictogen compounds Secondary alcohols Trialkylamines 25-azasteroid 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Amine Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Tertiary aliphatic amine Tertiary amine Cholesterol and derivatives Solid logp 5.74 ALOGPS logs -6.26 ALOGPS solubility 2.15e-04 g/l ALOGPS logp 5.21 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic 9.79 ChemAxon iupac (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-(dimethylamino)pentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol ChemAxon average_mass 387.6416 ChemAxon mono_mass 387.350115067 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C ChemAxon formula C26H45NO ChemAxon inchi InChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1 ChemAxon inchikey RZPPEFJMRVRCDD-XSLNCIIRSA-N ChemAxon polar_surface_area 23.47 ChemAxon refractivity 120.52 ChemAxon polarizability 50.04 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17192 Specdb::CMs 37897 Specdb::CMs 154552 Specdb::MsMs 304024 Specdb::MsMs 304025 Specdb::MsMs 304026 Specdb::MsMs 347128 Specdb::MsMs 347129 Specdb::MsMs 347130 Specdb::MsMs 2815210 Specdb::MsMs 2815211 Specdb::MsMs 2815212 Specdb::MsMs 2893145 Specdb::MsMs 2893146 Specdb::MsMs 2893147 HMDB01028 #<Reference:0x000055ce31aae7e0> #<Reference:0x000055ce31aae628> #<Reference:0x000055ce31aae470> #<Reference:0x000055ce31aae2b8> 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