1.0 2016-09-30 22:19:55 UTC 2020-05-21 16:29:05 UTC BMDB0000127 BMDB00127 D-Glucuronic acid D-Glucuronic acid, also known as glcaa or D-glucuronate, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. D-Glucuronic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Glucuronic acid exists in all living organisms, ranging from bacteria to humans. GlcAa GlcAalpha D-Glucuronate alpha-D-Glucopyranuronic acid alpha-D-Glucuronic acid D-(+)-Glucuronate D-(+)-Glucuronic acid GCU Glucosiduronate Glucosiduronic acid Glucuronate Glucuronic acid D-Glucopyranuronic acid alpha-D-Glucopyranosyluronic acid α-D-Glucopyranosyluronic acid α-D-Glucopyranuronic acid C6H10O7 194.1394 194.042652674 (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid glucuronic acid 6556-12-3 O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 AEMOLEFTQBMNLQ-WAXACMCWSA-N belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Glucuronic acid derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Oxacyclic compounds Oxanes Polyols Pyrans Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Glucuronic acid or derivatives Hemiacetal Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Organoheterocyclic compound Oxacycle Oxane Polyol Pyran Secondary alcohol Aliphatic heteromonocyclic compounds D-glucopyranuronic acid Solid melting_point 143 - 144 °C water_solubility 485 mg/mL logp -2.57 HANSCH,C ET AL. (1995) logp -2.30 ALOGPS logs 0.18 ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 3.21 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid ChemAxon average_mass 194.1394 ChemAxon mono_mass 194.042652674 ChemAxon smiles O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O ChemAxon formula C6H10O7 ChemAxon inchi InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 ChemAxon inchikey AEMOLEFTQBMNLQ-WAXACMCWSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 35.79 ChemAxon polarizability 16.32 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Inositol Metabolism SMP0087242 Starch and Sucrose Metabolism SMP0087252 Specdb::NmrTwoD 1156 Specdb::MsIr 195 Specdb::MsIr 196 Specdb::MsIr 197 Specdb::MsMs 192 Specdb::MsMs 193 Specdb::MsMs 319990 Specdb::MsMs 319991 Specdb::MsMs 319992 Specdb::MsMs 367270 Specdb::MsMs 367271 Specdb::MsMs 367272 Specdb::MsMs 2236268 Specdb::MsMs 2237099 Specdb::MsMs 2238362 Specdb::MsMs 2239234 Specdb::MsMs 2242475 Specdb::MsMs 2243401 Specdb::MsMs 2413042 Specdb::MsMs 2413043 Specdb::MsMs 2413044 Specdb::MsMs 2552132 Specdb::MsMs 2552133 Specdb::MsMs 2552134 Specdb::CMs 24385 Specdb::CMs 37309 Specdb::CMs 172924 Specdb::CMs 1051028 Specdb::CMs 1051030 Specdb::CMs 1051032 Specdb::CMs 1051034 Specdb::CMs 1051036 Specdb::CMs 1051037 Specdb::CMs 1051039 Specdb::CMs 1051041 Specdb::CMs 1051043 Specdb::CMs 1051045 Specdb::CMs 1051047 Specdb::CMs 1051049 Specdb::CMs 1051050 Specdb::CMs 1051052 Specdb::CMs 1051054 Specdb::CMs 1051056 Specdb::CMs 1051058 Specdb::CMs 1051060 Specdb::CMs 1051062 Specdb::CMs 1051064 Specdb::CMs 1051066 Specdb::CMs 1051067 Specdb::NmrOneD 1098 Specdb::NmrOneD 1156 Specdb::NmrOneD 142390 Specdb::NmrOneD 142391 Specdb::NmrOneD 142392 Specdb::NmrOneD 142393 Specdb::NmrOneD 142394 Specdb::NmrOneD 142395 Specdb::NmrOneD 142396 Specdb::NmrOneD 142397 Specdb::NmrOneD 142398 Specdb::NmrOneD 142399 Specdb::NmrOneD 142400 Specdb::NmrOneD 142401 Specdb::NmrOneD 142402 Specdb::NmrOneD 142403 Specdb::NmrOneD 142404 Specdb::NmrOneD 142405 Specdb::NmrOneD 142406 Specdb::NmrOneD 142407 Specdb::NmrOneD 142408 Specdb::NmrOneD 142409 Specdb::NmrOneD 166527 Kidney 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 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 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 Milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Placenta 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 Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 C00191 FDB021897 392615 444791 42717 C00001123 Glucuronic acid 34196 161 Hamayasu, Kenichi; Tadokoro, Hiroki; Kishino, Eriko; Ito, Tetsuya; Fujita, Koki; Hara, Kozo. Preparation of glucuronic acid and/or glucuronolactone from sucrose. PCT Int. Appl. (2006), 21pp. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 BMDBP00373 Dermatan-sulfate epimerase P0C2H4 DSE Enzyme BMDBP00424 Hyaluronidase-2 Q8SQG8 HYAL2 Enzyme BMDBP00425 Hyaluronidase-1 Q5E985 HYAL1 Enzyme BMDBP00426 Inositol oxygenase A7MBE4 MIOX Enzyme BMDBP02958 Beta-glucuronidase A3KMY8 GUSB Enzyme