1.0 2016-09-30 22:36:11 UTC 2020-05-11 20:21:33 UTC BMDB0000761 BMDB00761 Lithocholic acid (3alpha,5beta)-3-Hydroxycholan-24-Oic acid 3alpha-Hydroxy-5beta-cholanate 3alpha-Hydroxy-5beta-cholanic acid 3alpha-Hydroxy-5beta-cholanoic acid 5beta-Cholanic acid-3alpha-ol Lithocholate (3a,5b)-3-Hydroxycholan-24-Oate (3a,5b)-3-Hydroxycholan-24-Oic acid (3alpha,5beta)-3-Hydroxycholan-24-Oate (3Α,5β)-3-hydroxycholan-24-Oate (3Α,5β)-3-hydroxycholan-24-Oic acid 3a-Hydroxy-5b-cholanate 3a-Hydroxy-5b-cholanic acid 3Α-hydroxy-5β-cholanate 3Α-hydroxy-5β-cholanic acid 3a-Hydroxy-5b-cholanoate 3a-Hydroxy-5b-cholanoic acid 3alpha-Hydroxy-5beta-cholanoate 3Α-hydroxy-5β-cholanoate 3Α-hydroxy-5β-cholanoic acid 5b-Cholanate-3a-ol 5b-Cholanic acid-3a-ol 5beta-Cholanate-3alpha-ol 5Β-cholanate-3α-ol 5Β-cholanic acid-3α-ol Acid, lithocholic C24H40O3 376.5726 376.297745146 (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid 434-13-9 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 SMEROWZSTRWXGI-HVATVPOCSA-N belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Monohydroxy bile acids, alcohols and derivatives 3-alpha-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 3-alpha-hydroxysteroid 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid or derivatives Monohydroxy bile acid, alcohol, or derivatives Organic oxide Organic oxygen compound Organooxygen compound Secondary alcohol Aliphatic homopolycyclic compounds C24 bile acids, alcohols, and derivatives C24 bile acids, alcohols, and derivatives Cholane and derivatives bile acid monohydroxy-5beta-cholanic acid Solid logp 4.38 ALOGPS logs -5.87 ALOGPS logp 5.02 ChemAxon pka_strongest_acidic 4.79 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 376.5726 ChemAxon mono_mass 376.297745146 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O ChemAxon formula C24H40O3 ChemAxon inchi InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 ChemAxon inchikey SMEROWZSTRWXGI-HVATVPOCSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 107.68 ChemAxon polarizability 45.8 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 2279 Specdb::CMs 171424 Specdb::CMs 1074825 Specdb::CMs 1074827 Specdb::CMs 1074829 Specdb::CMs 1074831 Specdb::CMs 1074833 Specdb::CMs 1074835 Specdb::MsMs 1218118 Specdb::MsMs 1218119 Specdb::MsMs 1218120 Specdb::MsMs 1223257 Specdb::MsMs 1223258 Specdb::MsMs 1223259 Specdb::MsMs 1338901 Specdb::MsMs 1338902 Specdb::MsMs 1338903 Specdb::MsMs 2248311 Specdb::MsMs 2250076 Specdb::MsMs 2252028 Specdb::MsMs 2402480 Specdb::MsMs 2402481 Specdb::MsMs 2402482 Specdb::MsMs 2532918 Specdb::MsMs 2532919 Specdb::MsMs 2532920 Specdb::NmrTwoD 2005 Specdb::NmrOneD 5171 Specdb::NmrOneD 333698 Specdb::NmrOneD 333699 Specdb::NmrOneD 333700 Specdb::NmrOneD 333701 Specdb::NmrOneD 333702 Specdb::NmrOneD 333703 Specdb::NmrOneD 333704 Specdb::NmrOneD 333705 Specdb::NmrOneD 333706 Specdb::NmrOneD 333707 Specdb::NmrOneD 333708 Specdb::NmrOneD 333709 Specdb::NmrOneD 333710 Specdb::NmrOneD 333711 Specdb::NmrOneD 333712 Specdb::NmrOneD 333713 Specdb::NmrOneD 333714 Specdb::NmrOneD 333715 Specdb::NmrOneD 333716 Specdb::NmrOneD 333717 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C03990 FDB022230 9519 9903 C00051298 16325 CPD-7235 Lithocholic_acid 209 Xu, Zhengbang; Li, Kaixi; Zhao, Huaming. Synthesis of lithocholic acid by Huang-Min-Lon modification in the presence of crown ether. Sichuan Daxue Xuebao, Ziran Kexueban (1992), 29(4), 527-9. BMDBP01586 Bile acid receptor Q3SZL0 NR1H4 Enzyme