1.0 2016-09-30 22:19:45 UTC 2020-05-21 16:27:05 UTC BMDB0000118 BMDB00118 Homovanillic acid Homovanillic acid, also known as vanillacetate or homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Homovanillic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Homovanillic acid exists in all living species, ranging from bacteria to humans. Homovanillic acid participates in a number of enzymatic reactions, within cattle. In particular, Homovanillic acid can be biosynthesized from homovanillin; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, Homovanillic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxybenzeneacetic acid and guaiacol through its interaction with the enzyme catechol O-methyltransferase. In cattle, homovanillic acid is involved in the metabolic pathway called the tyrosine metabolism pathway. Homovanillic acid is a potentially toxic compound. (4-Hydroxy-3-methoxyphenyl)acetic acid 3-Methoxy-4-hydroxyphenylacetate 3-Methoxy-4-hydroxyphenylacetic acid 4-Hydroxy-3-methoxybenzeneacetic acid HVA Vanillacetic acid (4-Hydroxy-3-methoxyphenyl)acetate 4-Hydroxy-3-methoxybenzeneacetate Vanillacetate Homovanillate 3-Methoxy-4-hydroxy-phenylacetic acid 4-Hydroxy 3-methoxyphenylacetic acid 4-Hydroxy-3-methoxyphenylacetic acid Homovanilate Homovanilic acid Homovanillinic acid Vanilacetate Vanilacetic acid 3 Methoxy 4 hydroxyphenylacetic acid Acid, 3-methoxy-4-hydroxyphenylacetic Acid, 4-hydroxy-3-methoxyphenylacetic 4 Hydroxy 3 methoxyphenylacetic acid Acid, homovanillic 3'-Methoxy-4'-hydroxyphenylacetic acid 3’-methoxy-4’-hydroxyphenylacetic acid 4'-Hydroxy-3'-methoxy-phenylacetic acid 2-(4-Hydroxy-3-methoxyphenyl)acetic acid 4'-Hydroxy-3'-methoxyphenylacetic acid C9H10O4 182.1733 182.057908808 2-(4-hydroxy-3-methoxyphenyl)acetic acid homovanillic acid 306-08-1 COC1=CC(CC(O)=O)=CC=C1O InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12) QRMZSPFSDQBLIX-UHFFFAOYSA-N belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Organic compounds Benzenoids Phenols Methoxyphenols Methoxyphenols 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Methoxybenzenes Monocarboxylic acids and derivatives Organic oxides Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Anisole Aromatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Ether Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Aromatic homomonocyclic compounds monocarboxylic acid monomethoxybenzene phenols Solid melting_point 138 - 140 °C water_solubility 17 mg/mL logp 0.33 LAHANN,TR ET AL. (1989) logp 1.02 ALOGPS logs -1.83 ALOGPS logp 1.15 ChemAxon pka_strongest_acidic 3.74 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 2-(4-hydroxy-3-methoxyphenyl)acetic acid ChemAxon average_mass 182.1733 ChemAxon mono_mass 182.057908808 ChemAxon smiles COC1=CC(CC(O)=O)=CC=C1O ChemAxon formula C9H10O4 ChemAxon inchi InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12) ChemAxon inchikey QRMZSPFSDQBLIX-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 45.81 ChemAxon polarizability 17.74 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 2 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 Tyrosine Metabolism SMP0087235 Specdb::EiMs 952 Specdb::MsIr 183 Specdb::MsIr 184 Specdb::MsIr 185 Specdb::CMs 333 Specdb::CMs 1439 Specdb::CMs 2673 Specdb::CMs 27758 Specdb::CMs 30084 Specdb::CMs 30626 Specdb::CMs 31003 Specdb::CMs 32275 Specdb::CMs 37301 Specdb::CMs 151887 Specdb::CMs 1050349 Specdb::CMs 1050351 Specdb::CMs 1050353 Specdb::CMs 1050355 Specdb::CMs 1050357 Specdb::NmrTwoD 958 Specdb::NmrTwoD 1148 Specdb::MsMs 168 Specdb::MsMs 169 Specdb::MsMs 170 Specdb::MsMs 2903 Specdb::MsMs 2904 Specdb::MsMs 2905 Specdb::MsMs 2906 Specdb::MsMs 2907 Specdb::MsMs 10931 Specdb::MsMs 10932 Specdb::MsMs 10933 Specdb::MsMs 17603 Specdb::MsMs 17604 Specdb::MsMs 17605 Specdb::MsMs 437860 Specdb::MsMs 437861 Specdb::MsMs 437862 Specdb::MsMs 437863 Specdb::MsMs 437864 Specdb::MsMs 439681 Specdb::MsMs 439682 Specdb::MsMs 440166 Specdb::MsMs 2235866 Specdb::MsMs 2237219 Specdb::MsMs 2237495 Specdb::NmrOneD 1090 Specdb::NmrOneD 2330 Specdb::NmrOneD 3031 Specdb::NmrOneD 5071 Specdb::NmrOneD 5072 Specdb::NmrOneD 142270 Specdb::NmrOneD 142271 Specdb::NmrOneD 142272 Specdb::NmrOneD 142273 Specdb::NmrOneD 142274 Specdb::NmrOneD 142275 Specdb::NmrOneD 142276 Specdb::NmrOneD 142277 Specdb::NmrOneD 142278 Specdb::NmrOneD 142279 Specdb::NmrOneD 142280 Specdb::NmrOneD 142281 Specdb::NmrOneD 142282 Specdb::NmrOneD 142283 Specdb::NmrOneD 142284 Specdb::NmrOneD 142285 Specdb::NmrOneD 142286 Specdb::NmrOneD 142287 Specdb::NmrOneD 142288 Specdb::NmrOneD 142289 Brain 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 Fibroblasts 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 Fermented milk, by capillary electrophoresis-TOFMS Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. 26686724 C05582 FDB001783 1675 1738 545959 574 C00029504 CPD-7651 Homovanillic_acid 46066 971 Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. 26686724 BMDBP00421 Catechol O-methyltransferase A7MBI7 COMT Enzyme