1.0 2016-09-30 22:19:57 UTC 2020-05-21 16:28:38 UTC BMDB0000130 BMDB00130 Homogentisic acid Homogentisic acid, also known as homogentisate or acid, homogentisic, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Homogentisic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Homogentisic acid exists in all living organisms, ranging from bacteria to humans. Homogentisic acid is a potentially toxic compound. 2,5-Dihydroxyphenylacetic acid 2-(3,6-DIHYDROXYPHENYL)acetIC ACID 2,5-Dihydroxyphenylacetate 2-(3,6-DIHYDROXYPHENYL)acetate Homogentisate (2,5-Dihydroxyphenyl)-acetate (2,5-Dihydroxyphenyl)-acetic acid 2,5-Dihydroxy-a-toluate 2,5-Dihydroxy-a-toluic acid 2,5-Dihydroxy-alpha-toluate 2,5-Dihydroxy-alpha-toluic acid 2,5-Dihydroxy-benzeneacetate 2,5-Dihydroxy-benzeneacetic acid Alcapton Homogentisate acid Homogentisinate Homogentisinic acid Melanic acid Acid, homogentisic C8H8O4 168.1467 168.042258744 2-(2,5-dihydroxyphenyl)acetic acid homogentisic acid 451-13-8 OC(=O)CC1=C(O)C=CC(O)=C1 InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) IGMNYECMUMZDDF-UHFFFAOYSA-N belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Organic compounds Benzenoids Benzene and substituted derivatives Phenylacetic acids 2(hydroxyphenyl)acetic acids 1-hydroxy-2-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroquinones Monocarboxylic acids and derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid 2(hydroxyphenyl)acetic acid Aromatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroquinone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Phenol Aromatic homomonocyclic compounds dihydroxyphenylacetic acid hydroquinones Solid melting_point 153 °C water_solubility 850 mg/mL at 25 °C logp 0.86 SANGSTER (1994) logp 0.81 ALOGPS logs -1.32 ALOGPS logp 1 ChemAxon pka_strongest_acidic 3.57 ChemAxon pka_strongest_basic -5.9 ChemAxon iupac 2-(2,5-dihydroxyphenyl)acetic acid ChemAxon average_mass 168.1467 ChemAxon mono_mass 168.042258744 ChemAxon smiles OC(=O)CC1=C(O)C=CC(O)=C1 ChemAxon formula C8H8O4 ChemAxon inchi InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) ChemAxon inchikey IGMNYECMUMZDDF-UHFFFAOYSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 41.33 ChemAxon polarizability 15.57 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 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 Phenylalanine and Tyrosine Metabolism SMP0087218 Tyrosine Metabolism SMP0087235 Specdb::MsIr 16 Specdb::MsIr 70 Specdb::MsIr 201 Specdb::MsIr 202 Specdb::MsIr 203 Specdb::NmrOneD 1100 Specdb::NmrOneD 2389 Specdb::NmrOneD 3084 Specdb::NmrOneD 5812 Specdb::NmrOneD 5813 Specdb::NmrOneD 5814 Specdb::NmrOneD 5815 Specdb::NmrOneD 5816 Specdb::NmrOneD 5817 Specdb::NmrOneD 5818 Specdb::NmrOneD 5819 Specdb::NmrOneD 5820 Specdb::NmrOneD 5821 Specdb::NmrOneD 5822 Specdb::NmrOneD 5823 Specdb::NmrOneD 5824 Specdb::NmrOneD 5825 Specdb::NmrOneD 5826 Specdb::NmrOneD 5827 Specdb::NmrOneD 5828 Specdb::NmrOneD 5829 Specdb::NmrOneD 5830 Specdb::NmrOneD 5831 Specdb::MsMs 197 Specdb::MsMs 198 Specdb::MsMs 199 Specdb::MsMs 2993 Specdb::MsMs 2994 Specdb::MsMs 2995 Specdb::MsMs 2996 Specdb::MsMs 2997 Specdb::MsMs 2999 Specdb::MsMs 253974 Specdb::MsMs 253975 Specdb::MsMs 253976 Specdb::MsMs 273915 Specdb::MsMs 273916 Specdb::MsMs 273917 Specdb::MsMs 437865 Specdb::MsMs 437866 Specdb::MsMs 437867 Specdb::MsMs 437868 Specdb::MsMs 437869 Specdb::MsMs 439168 Specdb::MsMs 440170 Specdb::MsMs 2239828 Specdb::MsMs 2241873 Specdb::MsMs 2244010 Specdb::NmrTwoD 962 Specdb::NmrTwoD 1158 Specdb::CMs 350 Specdb::CMs 1493 Specdb::CMs 7481 Specdb::CMs 30103 Specdb::CMs 30570 Specdb::CMs 31014 Specdb::CMs 31851 Specdb::CMs 37311 Specdb::CMs 131454 Specdb::CMs 139188 Specdb::CMs 1051156 Specdb::CMs 1051158 Specdb::CMs 1051160 Specdb::CMs 1051161 Specdb::CMs 1051163 Specdb::CMs 1051165 Specdb::CMs 1051167 Specdb::CMs 1051169 Specdb::CMs 1051170 Specdb::CMs 1051172 Specdb::CMs 1051174 Specdb::CMs 1051176 Specdb::CMs 1051178 Cartilage 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 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 Milk Commercial milk, by CIL LC-MS Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 C00544 DB08327 FDB030907 759 780 44747 C00007309 Homogentisic_acid HOMOGENTISATE 1485308 331 Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 BMDBP00684 4-hydroxyphenylpyruvate dioxygenase Q5EA20 HPD Enzyme BMDBP02902 Homogentisate 1,2-dioxygenase B8YB76 HGD Enzyme