1.0 2011-09-21 00:23:13 UTC 2015-07-21 06:57:28 UTC FDB023010 (3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid b-D-GlucopyranosIduronic acid, (3a,5b,7a,12a)-24-[(carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl is found in the urine of leprosy patients. It is red in color similar to clofazimine. It is considered more polar than the parent drug. It is formed by hydrolytic deamination followed by glucuronidation.(PMID: 6120809) [HMDB] Glycocholic acid 3-glucuronide C32H51NO12 641.7468 641.341126101 (2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-4-(carboxymethylcarbamoyl)butan-2-yl]-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 99794-78-2 [H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C32H51NO12/c1-14(4-7-22(36)33-13-23(37)38)17-5-6-18-24-19(12-21(35)32(17,18)3)31(2)9-8-16(10-15(31)11-20(24)34)44-30-27(41)25(39)26(40)28(45-30)29(42)43/h14-21,24-28,30,34-35,39-41H,4-13H2,1-3H3,(H,33,36)(H,37,38)(H,42,43)/t14-,15+,16-,17?,18+,19+,20-,21+,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1 BWWWIHHYPYDOJQ-BSGVGGAOSA-N Solid logp 0.76 ALOGPS logs -3.38 ALOGPS solubility 2.70e-01 g/l ALOGPS logp -0.073 ChemAxon pka_strongest_acidic 3.29 ChemAxon pka_strongest_basic -0.4 ChemAxon iupac (2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 641.7468 ChemAxon mono_mass 641.341126101 ChemAxon smiles [H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O ChemAxon formula C32H51NO12 ChemAxon inchi InChI=1S/C32H51NO12/c1-14(4-7-22(36)33-13-23(37)38)17-5-6-18-24-19(12-21(35)32(17,18)3)31(2)9-8-16(10-15(31)11-20(24)34)44-30-27(41)25(39)26(40)28(45-30)29(42)43/h14-21,24-28,30,34-35,39-41H,4-13H2,1-3H3,(H,33,36)(H,37,38)(H,42,43)/t14-,15+,16-,17?,18+,19+,20-,21+,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1 ChemAxon inchikey BWWWIHHYPYDOJQ-BSGVGGAOSA-N ChemAxon polar_surface_area 223.31 ChemAxon refractivity 155.87 ChemAxon polarizability 66.73 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 12 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14798 Specdb::CMs 617804 Specdb::CMs 617805 Specdb::CMs 617806 Specdb::CMs 617807 Specdb::CMs 617808 Specdb::CMs 617809 Specdb::CMs 617810 Specdb::CMs 617811 Specdb::CMs 617812 Specdb::CMs 617813 Specdb::CMs 617814 Specdb::CMs 617815 Specdb::CMs 617816 Specdb::CMs 617817 Specdb::CMs 617818 Specdb::CMs 617819 Specdb::CMs 617820 Specdb::CMs 617821 Specdb::CMs 617822 Specdb::CMs 617823 Specdb::CMs 617824 Specdb::CMs 617825 Specdb::CMs 617826 Specdb::CMs 617827 Specdb::NmrOneD 122558 Specdb::NmrOneD 122559 Specdb::NmrOneD 122560 Specdb::NmrOneD 122561 Specdb::NmrOneD 122562 Specdb::NmrOneD 122563 Specdb::NmrOneD 122564 Specdb::NmrOneD 122565 Specdb::NmrOneD 122566 Specdb::NmrOneD 122567 Specdb::NmrOneD 122568 Specdb::NmrOneD 122569 Specdb::NmrOneD 122570 Specdb::NmrOneD 122571 Specdb::NmrOneD 122572 Specdb::NmrOneD 122573 Specdb::NmrOneD 122574 Specdb::NmrOneD 122575 Specdb::NmrOneD 122576 Specdb::NmrOneD 122577 Specdb::MsMs 60423 Specdb::MsMs 60424 Specdb::MsMs 60425 Specdb::MsMs 116739 Specdb::MsMs 116740 Specdb::MsMs 116741 Specdb::MsMs 2338282 Specdb::MsMs 2338283 Specdb::MsMs 2338284 Specdb::MsMs 2624870 Specdb::MsMs 2624871 Specdb::MsMs 2624872 HMDB02472 #<Reference:0x000055ce31c24d18> UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7