1.0 2016-09-30 22:28:11 UTC 2020-05-11 20:08:10 UTC BMDB0000307 BMDB00307 1b-Hydroxycholic acid 1b-Hydroxycholic acid, also known as 1b-hydroxycholate, 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. 1b-Hydroxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1b-Hydroxycholic acid exists in all living organisms, ranging from bacteria to humans. 1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oate 1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic acid 1b,3a,7a,12a-Tetrahydroxy-5b-cholanoate 1b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid 1b-Hydroxycholate (4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate (1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-Tetrahydroxycholan-24-oic acid (1β,3α,5β,7α,12α)-1,3,7,12-Tetrahydroxycholan-24-oic acid 1beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholan-24-oic acid 1beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid 1beta-Hydroxycholic acid 1β,3α,7α,12α-Tetrahydroxy-5β-cholan-24-oic acid 1β,3α,7α,12α-Tetrahydroxy-5β-cholanoic acid 1β-Hydroxycholic acid C24H40O6 424.5708 424.282489012 (4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid 80875-94-1 [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)C[C@@H](O)[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13+,14+,15-,16+,17+,18-,19-,20+,22+,23+,24-/m1/s1 UYVVLXVBEQAATF-WAIVXGPNSA-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. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Tetrahydroxy bile acids, alcohols and derivatives 1-hydroxysteroids 12-hydroxysteroids 3-alpha-hydroxysteroids 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Polyols Secondary alcohols 1-hydroxysteroid 12-hydroxysteroid 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Polyol Secondary alcohol Tetrahydroxy bile acid, alcohol, or derivatives Aliphatic homopolycyclic compounds C24 bile acids, alcohols, and derivatives Solid logp 1.34 ALOGPS logs -2.99 ALOGPS logp 1.18 ChemAxon pka_strongest_acidic 4.48 ChemAxon pka_strongest_basic -0.19 ChemAxon iupac (4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 424.5708 ChemAxon mono_mass 424.282489012 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)C[C@@H](O)[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O ChemAxon formula C24H40O6 ChemAxon inchi InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13+,14+,15-,16+,17+,18-,19-,20+,22+,23+,24-/m1/s1 ChemAxon inchikey UYVVLXVBEQAATF-WAIVXGPNSA-N ChemAxon polar_surface_area 118.22 ChemAxon refractivity 112.26 ChemAxon polarizability 47.72 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 5 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::MsMs 319420 Specdb::MsMs 319421 Specdb::MsMs 319422 Specdb::MsMs 366529 Specdb::MsMs 366530 Specdb::MsMs 366531 Specdb::MsMs 2303016 Specdb::MsMs 2303017 Specdb::MsMs 2303018 Specdb::MsMs 3065294 Specdb::MsMs 3065295 Specdb::MsMs 3065296 Specdb::CMs 24109 Specdb::CMs 37416 Specdb::CMs 166386 Specdb::CMs 1057508 Specdb::CMs 1057510 Specdb::CMs 1057512 Specdb::CMs 1057514 Specdb::CMs 1057516 Specdb::CMs 1057518 Specdb::CMs 1057520 Specdb::CMs 1057522 Specdb::CMs 1057524 Specdb::CMs 1057525 Specdb::CMs 1057527 Specdb::CMs 1057529 Specdb::CMs 1057531 Specdb::CMs 1057533 Specdb::CMs 1057535 Specdb::CMs 1057537 Specdb::CMs 1057539 Specdb::CMs 1057541 Specdb::CMs 1057543 Specdb::CMs 1057545 Specdb::CMs 1057547 Specdb::CMs 1057549 Gallbladder 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 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 Milk By GC-TOFMS and UPLC-QTOFMS Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311 FDB021934 4446981 5283893 5296 Tohma, Masahiko; Mahara, Reijiro; Takeshita, Hiromi; Kurosawa, Takao; Ikegawa, Shigeo; Nittono, Hiroshi. Synthesis of the 1b-hydroxylated bile acids and identification of 1b,3a,7a-trihydroxy- and 1b,3a,7a,12a-tetrahydroxy-5b-cholan-24-oic acids in human meconium. Chem Pharm Bull (Tokyo). 1985 Jul;33(7):3071-3. Pubmed: 4085062 Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. 27999311