2.0 2012-05-31 13:58:28 -0600 2015-09-13 12:56:12 -0600 ECMDB03325 M2MDB000489 Bilirubin diglucuronide Bilirubin diglucuronide is a water soluble version of bilirubin. E. coli living in the mammalian gut can use this compound as a substrate for growth. Bilirubin glucuronides are water-soluble. (2S,3S,4S,5R,6S)-6-[3-[2-[[3-[2-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-oxan-2-yl]oxycarbonylethyl]-5-[(E)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoyloxy]-3,4,5-trihydroxy-oxane-2-carboxylate (2S,3S,4S,5R,6S)-6-[3-[2-[[3-[2-[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-oxan-2-yl]oxycarbonylethyl]-5-[(E)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(E)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoyloxy]-3,4,5-trihydroxy-oxane-2-carboxylic acid Bilirubin &beta;-diglucuronide Bilirubin b-diglucuronide Bilirubin beta-diglucuronide Bilirubin β-diglucuronide Bilirubin-bisglucuronoside Bis(glucosyluronate)bilirubin Bis(glucosyluronic acid)bilirubin C45H52N4O18 936.921 936.32766085 (2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-{[(2E)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-{[(2E)-3-ethenyl-5-hydroxy-4-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 17459-92-6 [H]\C(C1=C(C)C(CCC(=O)O[C@]2([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)=C(CC2=C(CCC(=O)O[C@]3([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)C(C)=C(N2)C(\[H])=C2/N=C(O)C(C)=C2C=C)N1)=C1\N=C(O)C(C=C)=C1C InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13-,27-14-/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1 SCJLWMXOOYZBTH-BTVQFETGSA-N Solid Cytoplasm Periplasm logp 1.32 ALOGPS logs -3.87 ALOGPS solubility 1.26e-01 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 2.9 ChemAxon pka_strongest_basic 4.4 ChemAxon iupac (2S,3S,4S,5R,6S)-6-{[3-(2-{[3-(3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-oxopropyl)-5-{[(2E)-3-ethenyl-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 936.921 ChemAxon mono_mass 936.32766085 ChemAxon smiles [H]\C(C1=C(C)C(CCC(=O)O[C@]2([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)=C(CC2=C(CCC(=O)O[C@]3([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]3([H])O)C(C)=C(N2)C(\[H])=C2/N=C(O)C(C)=C2C=C)N1)=C1\N=C(O)C(C=C)=C1C ChemAxon formula C45H52N4O18 ChemAxon inchi InChI=1S/C45H52N4O18/c1-7-20-19(6)40(58)49-27(20)14-25-18(5)23(10-12-31(51)65-45-37(57)33(53)35(55)39(67-45)43(62)63)29(47-25)15-28-22(17(4)24(46-28)13-26-16(3)21(8-2)41(59)48-26)9-11-30(50)64-44-36(56)32(52)34(54)38(66-44)42(60)61/h7-8,13-14,32-39,44-47,52-57H,1-2,9-12,15H2,3-6H3,(H,48,59)(H,49,58)(H,60,61)(H,62,63)/b26-13-,27-14-/t32-,33-,34-,35-,36+,37+,38-,39-,44+,45+/m0/s1 ChemAxon inchikey SCJLWMXOOYZBTH-BTVQFETGSA-N ChemAxon polar_surface_area 363.8 ChemAxon refractivity 234.54 ChemAxon polarizability 97.04 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 18 ChemAxon donor_count 12 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Specdb::NmrOneD 10562 Specdb::NmrOneD 10563 Specdb::NmrOneD 10564 Specdb::NmrOneD 10565 Specdb::NmrOneD 10566 Specdb::NmrOneD 10567 Specdb::NmrOneD 10568 Specdb::NmrOneD 10569 Specdb::NmrOneD 10570 Specdb::NmrOneD 10571 Specdb::NmrOneD 10572 Specdb::NmrOneD 10573 Specdb::NmrOneD 10574 Specdb::NmrOneD 10575 Specdb::NmrOneD 10576 Specdb::NmrOneD 10577 Specdb::NmrOneD 10578 Specdb::NmrOneD 10579 Specdb::NmrOneD 10580 Specdb::NmrOneD 10581 Specdb::MsMs 1276213 Specdb::MsMs 1276214 Specdb::MsMs 1276215 Specdb::MsMs 1391152 Specdb::MsMs 1391153 Specdb::MsMs 1391154 Specdb::MsMs 2799751 Specdb::MsMs 2799752 Specdb::MsMs 2799753 Specdb::MsMs 2882690 Specdb::MsMs 2882691 Specdb::MsMs 2882692 HMDB03325 5459911 4573640 C05787 18392 BILIRUBIN-BISGLUCURONOSIDE Bilirubin diglucuronide Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 http://hmdb.ca/system/metabolites/msds/000/002/907/original/HMDB03325.pdf?1358462373 Beta-glucuronidase P05804 BGLR_ECOLI uidA http://ecmdb.ca/proteins/P05804.xml Glucuronide carrier protein P0CE45 UIDB2_ECOLI uidB http://ecmdb.ca/proteins/P0CE45.xml Bilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 Acceptor R04979