1.0 2011-09-21 00:15:00 UTC 2015-07-21 06:57:14 UTC FDB022502 27-Deoxy-5beta-cyprinol 27-Deoxy-5b-cyprinol is an intermediate in Bile acid synthesis pathway, in a sequence of reactions catalyzed by sterol 27-hydroxylase (CYP27) in the oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid (PMID: 8496170). 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol 3-glucuronide, a metabolite of 27-Deoxy-5b-cyprinol, is the major bile alcohol component in serum from cerebrotendinous xanthomatosis patients (PMID: 7920441) [HMDB] (25R)-5-beta-cholestane-3-alpha,7-alpha,12-alpha,26-tetraol (3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrol (3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,26-tetrol (3α,5β,7α,12α)-cholestane-3,7,12,26-tetrol 27-Deoxy-5b-cyprinol 3a,7a,12a,26-Tetrahydroxy-5b-cholestane 3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane 3α,7α,12α,26-tetrahydroxy-5β-cholestane 5-b-Cholestane-3a-7-tetraol 5-beta-cholestane-3-alpha-7-alpha-12-alpha-26-tetraol 5-beta-Cholestane-3a-7-tetraol 5b-Cholestane 3a,7a,12a,27-tetrol 5b-Cholestane-3a,7a,12a,26-tetraol 5b-Cholestane-3a,7a,12a,26-tetrol 5beta-Cholestane 3alpha,7alpha,12alpha,27-tetrol 5beta-Cholestane-3alpha,7alpha,12alpha,26-tetraol 5beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol 5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol 5beta-cholestane-3alpha,7alpha,12alpha,27alpha-tetrol 5β-cholestane 3α,7α,12α,27-tetrol 5β-cholestane-3α,7α,12α,26-tetraol 5β-cholestane-3α,7α,12α,26-tetrol Cholestane-3,7,12,26-tetrol Cholestane-3,7,12,26(27)-tetrol Cholestane-3,7,12,27-tetrol C27H48O4 436.6676 436.355260024 (1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol 5-cttl 862-53-3 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 XJZGNVBLVFOSKJ-XZULNKEGSA-N belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Tetrahydroxy bile acids, alcohols and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Aliphatic homopolycyclic compounds 12-hydroxysteroids 3-alpha-hydroxysteroids 7-hydroxysteroids Cyclic alcohols and derivatives Fatty alcohols Hydrocarbon derivatives Polyols Primary alcohols Secondary alcohols 12-hydroxysteroid 26-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Cyclic alcohol Fatty acyl Fatty alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Polyol Primary alcohol Secondary alcohol Tetrahydroxy bile acid, alcohol, or derivatives 12alpha-hydroxy steroid 26-hydroxy steroid 3alpha-hydroxy steroid 7alpha-hydroxy steroid C27 bile acids, alcohols, and derivatives C27 bile acids, alcohols, and derivatives Solid logp 3.77 ALOGPS logs -4.32 ALOGPS solubility 2.11e-02 g/l ALOGPS logp 3.62 ChemAxon pka_strongest_acidic 17.42 ChemAxon pka_strongest_basic -0.15 ChemAxon iupac (1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol ChemAxon average_mass 436.6676 ChemAxon mono_mass 436.355260024 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO ChemAxon formula C27H48O4 ChemAxon inchi InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1 ChemAxon inchikey XJZGNVBLVFOSKJ-XZULNKEGSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 124.73 ChemAxon polarizability 53.38 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Bile Acid Biosynthesis SMP00035 map00120 Specdb::CMs 12535 Specdb::CMs 37985 Specdb::CMs 132521 Specdb::CMs 140255 Specdb::MsMs 293593 Specdb::MsMs 293594 Specdb::MsMs 293595 Specdb::MsMs 334099 Specdb::MsMs 334100 Specdb::MsMs 334101 Specdb::MsMs 2337379 Specdb::MsMs 2337380 Specdb::MsMs 2337381 Specdb::MsMs 2629166 Specdb::MsMs 2629167 Specdb::MsMs 2629168 HMDB01231 #<Reference:0x000055ce31ddfc98> #<Reference:0x000055ce31ddfae0> 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