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. 2018 Feb 16;4(1):1–46. doi: 10.18053/jctres.04.201801.001

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Copyright © 2015, Whioce Publishing Pte. Ltd.

This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

This work is licensed under a Creative Commons Attribution 4.0 Unported License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

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Figure 3. — Non-exhaustive list of bile acid species and bile acid analogues, chemical properties, and toxicity. LogP (octanol:water partition coefficient) values were retrieved from PubChem and were predicted with XLogP2 or XLogP3 software. The 50% lethal concentration (LC50, used for in vitro data) and 50% lethal dose (LD50, used for in vivo data) were obtained from the material safety data sheets (retrieved from the Cayman Chemicals and Spectrum Chemical website) and the Toxicological Data Network (TOXNET, https://toxnet.nlm.nih.gov/) as well as available literature [544] [544]. Abbreviations (bile acids excluded): NA: information not available; iv: intravenous; ip: intraperitoneal; MW: molecular weight; sc: subcutaneous; TDLO; the lowest dose causing a toxic effect. Abbreviations (bile acids): 12-keto-LCA: 12-ketolithocholic acid / 12-oxolithocholic acid; 12-oxo-CDCA: 12-oxochenodeoxycholate / 12-oxochenodeoxycholic acid; 3,7-DiHCA : 3,7-dihydroxy-5-cholestenoic acid; 3,7-diketo-CA : 3,7-diketocholanic acid / 3,7-dioxhocholanoic acid; 3-keto-CA: 3-ketocholic acid / 3-oxocholic acid; 3-keto-LCA: 3-ketolithocholic acid / dehydrolithocholic acid; 3-SCDCA: chenodeoxycholic acid 3-sulfate; 3-S-GCDCA: glycochenodeoxycholic acid 3-sulfate; 3S-TLCA: taurolitocholate sulfate / taurolithocholic acid 3-sulfate; 3-sulfate CA: cholic acid 3-sulfate; 5-THCA: trihydrocoprostanic acid / (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholestane-5-carboxylic acid; 6-keto-LCA: 6- ketolithocholicacid;7-Hoca: 7α-hydroxy-3-oxo-4-cholestenoicacid;7-keto-DCA:7-ketodeoxycholicacid;7-keto-LCA:7- ketolithocholic acid / nutriacholic acid; 7-SCDCA: chenodeoxycholic acid 7-sulfate; 7-S-GCDCA: glycochenodeoxycholic acid 7- sulfate; 7-sulfate CA: cholic acid 7-sulfate; α-MCA: α-muricholate / α-muricholic acid / α-hyocholic acid; α-PCCA: α-phocaecholate / alpha-phocaecholic acid; β-MCA: β-muricholate / β-muricholic acid / β-hyocholic acid; β-PCCA: β-phocaecholate / phocaecholic acid; ω-MCA: ω-muricholate / ω-muricholic acid / ω-hyocholic acid; ACA: allocholate / allocholic acid; AlloAVCA: alloavicholate / alloavicholic acid; AlloCDCA: allochenodeoxycholate / allochenodeoxycholic acid; AlloDCA: allodeoxycholate / allodeoxycholic acid; AlloLCA: allolithocholic acid; AlloUDCA: alloursodeoxycholic acid; ApoCA: apocholate / apocholic acid; AVCA: avicholate / avicholic acid; AVDCA: avideoxycholate / avideoxycholic acid; BCA: bitocholate / bitocholic acid; CA: cholate / cholic acid; CCA: ciliatocholate / ciliatocholic acid; CDCA: chenodeoxycholate / chenodeoxycholic acid; CGA: cygnocholate / cygnocholic acid; CSA: cholestenoic acid; DCA: deoxycholate / deoxycholic acid; DHA: dehydrocholate / dehydrocholic acid; DiHCA: dihydroxycoprostanoic acid; DinorCA: dinorcholic acid; DinorCDCA: dinorchenodeoxycholic acid; DinorDCA: dinordeoxycholic acid; DinorHDCA: dinorhyodeoxycholic acid; DinorLCA: dinorlithocholic acid; DinorUDCA: dinorursodeoxycholic acid; GCA: glycocholate / glycocholic acid; GCDCA: glycochenodeoxycholate / glycochenodeoxycholic acid; GDCA: glycodeoxycholate / glycodeoxycholic acid; GHCA: glycohyocholate / glycohyocholic acid; GHDCA: glycohyodeoxycholate / glycohyodeoxycholic acid; GLCA: glycolithocholate / glycolithocholic acid; GLCA-3-S: glycolithocholate 3-sulfate / glycolithocholic acid 3-sulfate; Glyco-OCA: glyco-obeticholic acid; GUCA: glycoursocholate / glycoursocholic acid; GUDCA: glycoursodeoxycholate / glycoursodeoxycholic acid; HCA: hemulcholate / hemulcholic acid; HDCA: hyodeoxycholic acid / murideoxycholic acid; LagoDCA: lagodeoxycholic acid; LCA: lithocholate / lithocholic acid; NorCA: norcholate / norcholic acid; NorCDCA: norchenodeoxycholic acid; NorDCA: nordeoxycholic acid; NorHDCA: norhyodeoxycholic acid; NorLCA: norlithocholic acid; NorUCA: noruroscholic acid; NorUDCA: norursodeoxycholic acid; OCA: obeticholic acid / ocaliva / 6-ethylchenodeoxycholic acid / INT-747; PCA: pythocholic acid; S-LCA: lithocholic acid 3-sulfate; T-alpha-MC: tauro-α-muricholic acid; T-beta-MC: tauro-β-muricholic acid; TCA: taurocholate / taurocholic acid; TCA-3-S: taurocholate 3-sulfate / taurocholic acid 3-sulfate; TCDCA: taurochenodeoxycholate / taurochenodeoxycholic acid; TCDCA3S: taurochenodeoxycholic acid 3-sulfate; TCDCA7S: taurochenodeoxycholic acid 7-sulfate; TDC(A): taurodeoxycholate / taurodeoxycholic acid; THCA: trihydrocoprostanic acid / coprocholic acid / 3,7,12-trihydroxycholestan-26-oic acid; THDCA: taurohyodeoxycholate / taurohyodeoxycholic acid; TLCA: taurolithocholate / taurolithocholic acid; TUCA: tauroursocholate / tauroursocholic acid; TUDCA: tauroursodeoxycholate / tauroursodeoxycholic acid; UA: ursolic acid; UCA: ursocholic acid; UClA: ursocholanic acid; UDCA: ursodeoxycholate / ursodeoxycholic acid; VA: varanic acid; VCA: vulpecholate / vulpecholic acid.

Figure 3. — Non-exhaustive list of bile acid species and bile acid analogues, chemical properties, and toxicity. LogP (octanol:water partition coefficient) values were retrieved from PubChem and were predicted with XLogP2 or XLogP3 software. The 50% lethal concentration (LC50, used for in vitro data) and 50% lethal dose (LD50, used for in vivo data) were obtained from the material safety data sheets (retrieved from the Cayman Chemicals and Spectrum Chemical website) and the Toxicological Data Network (TOXNET, https://toxnet.nlm.nih.gov/) as well as available literature [544] [544]. Abbreviations (bile acids excluded): NA: information not available; iv: intravenous; ip: intraperitoneal; MW: molecular weight; sc: subcutaneous; TDLO; the lowest dose causing a toxic effect. Abbreviations (bile acids): 12-keto-LCA: 12-ketolithocholic acid / 12-oxolithocholic acid; 12-oxo-CDCA: 12-oxochenodeoxycholate / 12-oxochenodeoxycholic acid; 3,7-DiHCA : 3,7-dihydroxy-5-cholestenoic acid; 3,7-diketo-CA : 3,7-diketocholanic acid / 3,7-dioxhocholanoic acid; 3-keto-CA: 3-ketocholic acid / 3-oxocholic acid; 3-keto-LCA: 3-ketolithocholic acid / dehydrolithocholic acid; 3-SCDCA: chenodeoxycholic acid 3-sulfate; 3-S-GCDCA: glycochenodeoxycholic acid 3-sulfate; 3S-TLCA: taurolitocholate sulfate / taurolithocholic acid 3-sulfate; 3-sulfate CA: cholic acid 3-sulfate; 5-THCA: trihydrocoprostanic acid / (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholestane-5-carboxylic acid; 6-keto-LCA: 6- ketolithocholicacid;7-Hoca: 7α-hydroxy-3-oxo-4-cholestenoicacid;7-keto-DCA:7-ketodeoxycholicacid;7-keto-LCA:7- ketolithocholic acid / nutriacholic acid; 7-SCDCA: chenodeoxycholic acid 7-sulfate; 7-S-GCDCA: glycochenodeoxycholic acid 7- sulfate; 7-sulfate CA: cholic acid 7-sulfate; α-MCA: α-muricholate / α-muricholic acid / α-hyocholic acid; α-PCCA: α-phocaecholate / alpha-phocaecholic acid; β-MCA: β-muricholate / β-muricholic acid / β-hyocholic acid; β-PCCA: β-phocaecholate / phocaecholic acid; ω-MCA: ω-muricholate / ω-muricholic acid / ω-hyocholic acid; ACA: allocholate / allocholic acid; AlloAVCA: alloavicholate / alloavicholic acid; AlloCDCA: allochenodeoxycholate / allochenodeoxycholic acid; AlloDCA: allodeoxycholate / allodeoxycholic acid; AlloLCA: allolithocholic acid; AlloUDCA: alloursodeoxycholic acid; ApoCA: apocholate / apocholic acid; AVCA: avicholate / avicholic acid; AVDCA: avideoxycholate / avideoxycholic acid; BCA: bitocholate / bitocholic acid; CA: cholate / cholic acid; CCA: ciliatocholate / ciliatocholic acid; CDCA: chenodeoxycholate / chenodeoxycholic acid; CGA: cygnocholate / cygnocholic acid; CSA: cholestenoic acid; DCA: deoxycholate / deoxycholic acid; DHA: dehydrocholate / dehydrocholic acid; DiHCA: dihydroxycoprostanoic acid; DinorCA: dinorcholic acid; DinorCDCA: dinorchenodeoxycholic acid; DinorDCA: dinordeoxycholic acid; DinorHDCA: dinorhyodeoxycholic acid; DinorLCA: dinorlithocholic acid; DinorUDCA: dinorursodeoxycholic acid; GCA: glycocholate / glycocholic acid; GCDCA: glycochenodeoxycholate / glycochenodeoxycholic acid; GDCA: glycodeoxycholate / glycodeoxycholic acid; GHCA: glycohyocholate / glycohyocholic acid; GHDCA: glycohyodeoxycholate / glycohyodeoxycholic acid; GLCA: glycolithocholate / glycolithocholic acid; GLCA-3-S: glycolithocholate 3-sulfate / glycolithocholic acid 3-sulfate; Glyco-OCA: glyco-obeticholic acid; GUCA: glycoursocholate / glycoursocholic acid; GUDCA: glycoursodeoxycholate / glycoursodeoxycholic acid; HCA: hemulcholate / hemulcholic acid; HDCA: hyodeoxycholic acid / murideoxycholic acid; LagoDCA: lagodeoxycholic acid; LCA: lithocholate / lithocholic acid; NorCA: norcholate / norcholic acid; NorCDCA: norchenodeoxycholic acid; NorDCA: nordeoxycholic acid; NorHDCA: norhyodeoxycholic acid; NorLCA: norlithocholic acid; NorUCA: noruroscholic acid; NorUDCA: norursodeoxycholic acid; OCA: obeticholic acid / ocaliva / 6-ethylchenodeoxycholic acid / INT-747; PCA: pythocholic acid; S-LCA: lithocholic acid 3-sulfate; T-alpha-MC: tauro-α-muricholic acid; T-beta-MC: tauro-β-muricholic acid; TCA: taurocholate / taurocholic acid; TCA-3-S: taurocholate 3-sulfate / taurocholic acid 3-sulfate; TCDCA: taurochenodeoxycholate / taurochenodeoxycholic acid; TCDCA3S: taurochenodeoxycholic acid 3-sulfate; TCDCA7S: taurochenodeoxycholic acid 7-sulfate; TDC(A): taurodeoxycholate / taurodeoxycholic acid; THCA: trihydrocoprostanic acid / coprocholic acid / 3,7,12-trihydroxycholestan-26-oic acid; THDCA: taurohyodeoxycholate / taurohyodeoxycholic acid; TLCA: taurolithocholate / taurolithocholic acid; TUCA: tauroursocholate / tauroursocholic acid; TUDCA: tauroursodeoxycholate / tauroursodeoxycholic acid; UA: ursolic acid; UCA: ursocholic acid; UClA: ursocholanic acid; UDCA: ursodeoxycholate / ursodeoxycholic acid; VA: varanic acid; VCA: vulpecholate / vulpecholic acid.