1.0 2016-09-30 22:32:02 UTC 2020-05-11 20:00:42 UTC BMDB0000518 BMDB00518 Chenodeoxycholic acid 3alpha,7alpha-Dihydroxy-5beta-cholanic acid 7alpha-Hydroxylithocholic acid Anthropodeoxycholic acid Anthropodesoxycholic acid CDCA Chenic acid Chenix Chenodiol Gallodesoxycholic acid 3a,7a-Dihydroxy-5b-cholanate 3a,7a-Dihydroxy-5b-cholanic acid 3alpha,7alpha-Dihydroxy-5beta-cholanate 3Α,7α-dihydroxy-5β-cholanate 3Α,7α-dihydroxy-5β-cholanic acid 7a-Hydroxylithocholate 7a-Hydroxylithocholic acid 7alpha-Hydroxylithocholate 7Α-hydroxylithocholate 7Α-hydroxylithocholic acid Anthropodeoxycholate Anthropodesoxycholate Chenate Gallodesoxycholate Chenodeoxycholate (+)-Chenodeoxycholate (+)-Chenodeoxycholic acid (3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oate (3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acid 3a,7a-Dihydroxy-5b,14a,17b-cholanate 3a,7a-Dihydroxy-5b,14a,17b-cholanic acid 3a,7a-Dihydroxy-5b-cholan-24-Oate 3a,7a-Dihydroxy-5b-cholan-24-Oic acid 7a-Hydroxy-desoxycholsaeure Chenodesoxycholsaeure Acid, chenique Chenofalk Chenophalk Acid, chenodeoxycholic Chenodeoxycholate, sodium Quenocol Solvay brand OF chenodeoxycholic acid Antigen brand OF chenodeoxycholic acid Falk brand OF chenodeoxycholic acid Quenobilan Sodium chenodeoxycholate Tramedico brand OF chenodeoxycholic acid Zambon brand OF chenodeoxycholic acid Acid, chenic Acid, gallodesoxycholic Chenique acid Estedi brand OF chenodeoxycholic acid Henohol C24H40O4 392.572 392.292659768 (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid 474-25-9 [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])CC[C@]12C)[C@H](C)CCC(O)=O InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1 RUDATBOHQWOJDD-BSWAIDMHSA-N belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Bile acids, alcohols and derivatives Dihydroxy bile acids, alcohols and derivatives 3-alpha-hydroxysteroids 7-hydroxysteroids Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols 3-alpha-hydroxysteroid 3-hydroxysteroid 7-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Dihydroxy bile acid, alcohol, or derivatives Hydrocarbon derivative Hydroxysteroid Monocarboxylic acid 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 dihydroxy-5beta-cholanic acid Solid melting_point 165 - 167 °C water_solubility 0.0899 mg/mL logp 4.15 SANGSTER (1993) logp 3.01 ALOGPS logs -4.30 ALOGPS logp 3.71 ChemAxon pka_strongest_acidic 4.6 ChemAxon pka_strongest_basic -0.54 ChemAxon iupac (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid ChemAxon average_mass 392.572 ChemAxon mono_mass 392.292659768 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])CC[C@]12C)[C@H](C)CCC(O)=O ChemAxon formula C24H40O4 ChemAxon inchi InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1 ChemAxon inchikey RUDATBOHQWOJDD-BSWAIDMHSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 109.27 ChemAxon polarizability 46.35 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 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 Bile Acid Biosynthesis SMP0087236 Specdb::NmrOneD 1405 Specdb::NmrTwoD 1349 Specdb::MsMs 743 Specdb::MsMs 744 Specdb::MsMs 745 Specdb::MsMs 245607 Specdb::MsMs 245608 Specdb::MsMs 245609 Specdb::MsMs 265554 Specdb::MsMs 265555 Specdb::MsMs 265556 Specdb::MsMs 438647 Specdb::MsMs 2238439 Specdb::MsMs 2239154 Specdb::MsMs 2239839 Specdb::MsMs 2241884 Specdb::MsMs 2241925 Specdb::MsMs 2244740 Specdb::MsMs 2245397 Specdb::MsMs 2246845 Specdb::MsMs 2247425 Specdb::MsMs 2248856 Specdb::MsMs 2249553 Specdb::MsMs 2251565 Specdb::MsMs 2833170 Specdb::MsMs 2833171 Specdb::MsMs 2833172 Specdb::CMs 2289 Specdb::CMs 18271 Specdb::CMs 31162 Specdb::CMs 37589 Specdb::CMs 134069 Specdb::CMs 141803 Specdb::CMs 1064730 Specdb::CMs 1064732 Specdb::CMs 1064734 Specdb::CMs 1064736 Specdb::CMs 1064738 Specdb::CMs 1064740 Specdb::CMs 1064742 Specdb::CMs 1064744 Specdb::CMs 1064746 Specdb::CMs 1064748 Specdb::CMs 1064750 Specdb::CMs 1064752 Specdb::CMs 1064754 Fibroblasts 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 Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 DB06777 FDB022087 9728 16755 10133 C02528 Chenodiol 207 Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8. BMDBP01586 Bile acid receptor Q3SZL0 NR1H4 Enzyme