1.0 2016-09-30 22:18:32 UTC 2020-06-04 20:37:20 UTC BMDB0000020 BMDB00020 p-Hydroxyphenylacetic acid 4-Hydroxyphenylacetic acid, also known as (p-hydroxyphenyl)acetate or 4-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-Hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylacetic acid is a potentially toxic compound. 4-Hydroxyphenylacetic acid has been found to be associated with several diseases known as lung cancer, crohn's disease, spina bifida, and epilepsy; also 4-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria. (p-Hydroxyphenyl)acetic acid 4-Carboxymethylphenol 4-Hydroxybenzeneacetic acid 4-Hydroxyphenylacetate 4-Hydroxyphenylacetic acid (p-Hydroxyphenyl)acetate 4-Hydroxybenzeneacetate p-Hydroxyphenylacetate (4-Hydroxy-phenyl)-acetate (4-Hydroxy-phenyl)-acetic acid (4-Hydroxy-phenyl)-essigsaeure (4-Hydroxyphenyl)acetate (4-Hydroxyphenyl)acetic acid (p-Hydroxyphenyl)-acetate (p-Hydroxyphenyl)-acetic acid 4-Hydroxy-benzeneacetate 4-Hydroxy-benzeneacetic acid 4-Hydroxyphenyl-acetic acid Parahydroxy phenylacetate Parahydroxy phenylacetic acid Parahydroxyphenylacetate Para-hydroxyphenylacetic acid p-Hydroxyphenylacetic acid 4'-Hydroxyphenylacetic acid 2-(4-Hydroxyphenyl)acetic acid C8H8O3 152.1473 152.047344122 2-(4-hydroxyphenyl)acetic acid 4-hydroxyphenylacetic acid 156-38-7 OC(=O)CC1=CC=C(O)C=C1 InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) XQXPVVBIMDBYFF-UHFFFAOYSA-N belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Organic compounds Benzenoids Phenols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Aromatic homomonocyclic compounds monocarboxylic acid phenols Solid melting_point 148 - 150 °C water_solubility 60.7 mg/mL logp 0.75 HANSCH,C ET AL. (1995) logp 0.93 ALOGPS logs -1.33 ALOGPS logp 1.31 ChemAxon pka_strongest_acidic 4 ChemAxon pka_strongest_basic -6 ChemAxon iupac 2-(4-hydroxyphenyl)acetic acid ChemAxon average_mass 152.1473 ChemAxon mono_mass 152.047344122 ChemAxon smiles OC(=O)CC1=CC=C(O)C=C1 ChemAxon formula C8H8O3 ChemAxon inchi InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) ChemAxon inchikey XQXPVVBIMDBYFF-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 39.35 ChemAxon polarizability 14.83 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 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::MsIr 100 Specdb::MsIr 101 Specdb::MsIr 102 Specdb::EiMs 234 Specdb::NmrTwoD 927 Specdb::CMs 284 Specdb::CMs 285 Specdb::CMs 286 Specdb::CMs 287 Specdb::CMs 1313 Specdb::CMs 2422 Specdb::CMs 27534 Specdb::CMs 28712 Specdb::CMs 30037 Specdb::CMs 30169 Specdb::CMs 30258 Specdb::CMs 30455 Specdb::CMs 30749 Specdb::CMs 30955 Specdb::CMs 31842 Specdb::CMs 37248 Specdb::CMs 171718 Specdb::CMs 1047017 Specdb::CMs 1047019 Specdb::CMs 1047020 Specdb::CMs 1047022 Specdb::CMs 1047024 Specdb::MsMs 33 Specdb::MsMs 34 Specdb::MsMs 35 Specdb::MsMs 2555 Specdb::MsMs 2556 Specdb::MsMs 2557 Specdb::MsMs 2558 Specdb::MsMs 2559 Specdb::MsMs 2560 Specdb::MsMs 2561 Specdb::MsMs 178116 Specdb::MsMs 178117 Specdb::MsMs 178118 Specdb::MsMs 180432 Specdb::MsMs 180433 Specdb::MsMs 180434 Specdb::MsMs 437776 Specdb::MsMs 437777 Specdb::MsMs 437778 Specdb::MsMs 437779 Specdb::MsMs 437780 Specdb::MsMs 439738 Specdb::MsMs 439739 Specdb::MsMs 449840 Specdb::MsMs 449841 Specdb::NmrOneD 1034 Specdb::NmrOneD 1121 Specdb::NmrOneD 2255 Specdb::NmrOneD 5047 Specdb::NmrOneD 5048 Specdb::NmrOneD 141890 Specdb::NmrOneD 141891 Specdb::NmrOneD 141892 Specdb::NmrOneD 141893 Specdb::NmrOneD 141894 Specdb::NmrOneD 141895 Specdb::NmrOneD 141896 Specdb::NmrOneD 141897 Specdb::NmrOneD 141898 Specdb::NmrOneD 141899 Specdb::NmrOneD 141900 Specdb::NmrOneD 141901 Specdb::NmrOneD 141902 Specdb::NmrOneD 141903 Specdb::NmrOneD 141904 Specdb::NmrOneD 141905 Specdb::NmrOneD 141906 Specdb::NmrOneD 141907 Specdb::NmrOneD 141908 Specdb::NmrOneD 141909 Bladder 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 Epidermis 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 whole milk with 3.25% fat Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Prostate Tissue 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 78510 +/- 12590 uM O'Grady L, Doherty ML, Mulligan FJ: Subacute ruminal acidosis (SARA) in grazing Irish dairy cows. Vet J. 2008 Apr;176(1):44-9. doi: 10.1016/j.tvjl.2007.12.017. Epub 2008 Mar 6. 18328751 Urine 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 C00642 FDB010534 124 18101 127 573 35599 4-hydroxyphenylacetic_acid 130 4-HYDROXYPHENYLACETATE Qiao, Xi-long; Tian, Hui; Li, Wen; Zhao, Xiu-yun; Zhang, Jin-fang. Study of 4-hydroxyphenylacetic acid synthesis from glyoxalic acid. Hebei Gongye Keji (2005), 22(5), 264-266. 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 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 BMDBP00989 Aldehyde dehydrogenase family 3 member B1 Q1JPA0 ALDH3B1 Enzyme