2.0 2012-05-31 10:27:02 -0600 2015-09-13 12:56:08 -0600 ECMDB00500 M2MDB000143 4-Hydroxybenzoic acid 4-Hydroxybenzoic acid, or p-hydroxybenzoic acid, is a phenolic derivative of benzoic acid. It a white crystalline solid that is slightly soluble in water and chloroform, but well soluble in alcohols, ether, and acetone. 4-Carboxyphenol 4-Hydroxy-benzoate 4-Hydroxy-benzoesaeure 4-Hydroxy-benzoic acid 4-Hydroxybenzoate 4-Hydroxybenzoic acid <i>p</i>-hydroxybenzoate P-Carboxyphenol P-Hydroxy-Benzoate P-Hydroxy-Benzoic acid P-Hydroxybenzoate P-Hydroxybenzoic acid P-Salicylate P-Salicylic acid Paraben-acid PHBA C7H6O3 138.1207 138.031694058 4-hydroxybenzoic acid P-hydroxybenzoic acid 99-96-7 OC(=O)C1=CC=C(O)C=C1 InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) FJKROLUGYXJWQN-UHFFFAOYSA-N Solid Cytosol logp 1.58 ALOGPS logs -1.06 ALOGPS solubility 1.19e+01 g/l ALOGPS logp 1.33 ChemAxon pka_strongest_acidic 4.38 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac 4-hydroxybenzoic acid ChemAxon average_mass 138.1207 ChemAxon mono_mass 138.031694058 ChemAxon smiles OC(=O)C1=CC=C(O)C=C1 ChemAxon formula C7H6O3 ChemAxon inchi InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) ChemAxon inchikey FJKROLUGYXJWQN-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 35.3 ChemAxon polarizability 12.94 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Phenylalanine metabolism The pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine. Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter. L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid. L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP. The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter. PW000921 ec00360 Metabolic Ubiquinone and other terpenoid-quinone biosynthesis ec00130 Benzoate degradation via hydroxylation ec00362 1,4-Dichlorobenzene degradation ec00627 Microbial metabolism in diverse environments ec01120 Toluene degradation ec00623 Bisphenol degradation ec00363 Metabolic pathways eco01100 Secondary Metabolites: Ubiquinol biosynthesis The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW000981 Metabolic Secondary Metabolites: Ubiquinol biosynthesis 2 The biosynthesis of ubiquinol starts the interaction of 4-hydroxybenzoic acid interacting with an octaprenyl diphosphate. The former compound comes from the chorismate interacting with a chorismate lyase resulting in the release of a pyruvic acid and a 4-hydroxybenzoic acid. On the other hand, the latter compound, octaprenyl diphosphate is the result of a farnesyl pyrophosphate interacting with an isopentenyl pyrophosphate through an octaprenyl diphosphate synthase resulting in the release of a pyrophosphate and an octaprenyl diphosphate. The 4-hydroxybenzoic acid interacts with octaprenyl diphosphate through a 4-hydroxybenzoate octaprenyltransferase resulting in the release of a pyrophosphate and a 3-octaprenyl-4-hydroxybenzoate. The latter compound then interacts with a hydrogen ion through a 3-octaprenyl-4-hydroxybenzoate carboxy-lyase resulting in the release of a carbon dioxide and a 2-octaprenylphenol. The latter compound interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenylphenol hydroxylase resulting in a NADP, a water molecule and a 2-octaprenyl-6-hydroxyphenol. The 2-octaprenyl-6-hydroxyphenol interacts with an S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in the release of a hydrogen ion, an s-adenosylhomocysteine and a 2-methoxy-6-(all-trans-octaprenyl)phenol. The latter compound then interacts with an oxygen molecule and a hydrogen ion through a NADPH driven 2-octaprenyl-6-methoxyphenol hydroxylase resulting in a NADP, a water molecule and a 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol. The latter compound interacts with a S-adenosylmethionine through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a s-adenosylhomocysteine, a hydrogen ion and a 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. The 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol. interacts with a reduced acceptor, an oxygen molecule through a 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase resulting in the release of a water molecule, an oxidized electron acceptor and a 3-demethylubiquinol-8. The latter compound then interacts with a S-adenosylmethionine through a bifunctional 3-demethylubiquinone-8 3-O-methyltransferase and 2-octaprenyl-6-hydroxyphenol methylase resulting in a hydrogen ion, a S-adenosylhomocysteine and a ubiquinol 8. PW002036 Metabolic Specdb::CMs 562 Specdb::CMs 563 Specdb::CMs 564 Specdb::CMs 1306 Specdb::CMs 3055 Specdb::CMs 27535 Specdb::CMs 29091 Specdb::CMs 29550 Specdb::CMs 29661 Specdb::CMs 29780 Specdb::CMs 30128 Specdb::CMs 30329 Specdb::CMs 30670 Specdb::CMs 30925 Specdb::CMs 31155 Specdb::CMs 31881 Specdb::CMs 37574 Specdb::CMs 161901 Specdb::CMs 1064187 Specdb::CMs 1064189 Specdb::CMs 1064191 Specdb::CMs 1064192 Specdb::CMs 1064194 Specdb::EiMs 1592 Specdb::NmrOneD 1394 Specdb::NmrOneD 4014 Specdb::NmrOneD 4301 Specdb::NmrOneD 4898 Specdb::NmrOneD 4899 Specdb::NmrOneD 6942 Specdb::NmrOneD 6943 Specdb::NmrOneD 6944 Specdb::NmrOneD 6945 Specdb::NmrOneD 6946 Specdb::NmrOneD 6947 Specdb::NmrOneD 6948 Specdb::NmrOneD 6949 Specdb::NmrOneD 6950 Specdb::NmrOneD 6951 Specdb::NmrOneD 6952 Specdb::NmrOneD 6953 Specdb::NmrOneD 6954 Specdb::NmrOneD 6955 Specdb::NmrOneD 6956 Specdb::NmrOneD 6957 Specdb::NmrOneD 6958 Specdb::NmrOneD 6959 Specdb::NmrOneD 6960 Specdb::NmrOneD 6961 Specdb::MsMs 716 Specdb::MsMs 717 Specdb::MsMs 718 Specdb::MsMs 4111 Specdb::MsMs 4112 Specdb::MsMs 4113 Specdb::MsMs 4114 Specdb::MsMs 4115 Specdb::MsMs 4116 Specdb::MsMs 4117 Specdb::MsMs 4118 Specdb::MsMs 4122 Specdb::MsMs 4123 Specdb::MsMs 4124 Specdb::MsMs 179391 Specdb::MsMs 179392 Specdb::MsMs 179393 Specdb::MsMs 181719 Specdb::MsMs 181720 Specdb::MsMs 181721 Specdb::MsMs 374047 Specdb::MsMs 437771 Specdb::MsMs 437772 Specdb::MsMs 437773 Specdb::MsMs 437774 Specdb::NmrTwoD 1021 Specdb::NmrTwoD 1338 HMDB00500 135 132 C00156 30763 4-hydroxybenzoate PHB 4-Hydroxybenzoic acid Keseler, I. 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Khimiya i Industriya (1922-1988) (1966), 38(10), 458-63. http://hmdb.ca/system/metabolites/msds/000/000/419/original/HMDB00500.pdf?1358461253 Chorismate--pyruvate lyase P26602 UBIC_ECOLI ubiC http://ecmdb.ca/proteins/P26602.xml 4-hydroxybenzoate octaprenyltransferase P0AGK1 UBIA_ECOLI ubiA http://ecmdb.ca/proteins/P0AGK1.xml acetyl esterase (EC:3.1.1.-) P23872 aes http://ecmdb.ca/proteins/P23872.xml Chorismate <> 4-Hydroxybenzoic acid + Pyruvic acid R01302 CHORPYRLY-RXN 4-Hydroxybenzoic acid + Octaprenyl diphosphate > 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate R05615 4-Hydroxybenzoic acid + Pyruvic acid <> Chorismate R01302 all-trans-Polyprenyl diphosphate + 4-Hydroxybenzoic acid + Geranyl-PP <> 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate + 4-Hydroxy-3-polyprenylbenzoate R05000 Octaprenyl diphosphate + 4-Hydroxybenzoic acid <> 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate R05615 4-Hydroxyphenyl-4-hydroxybenzoate + Water <> 4-Hydroxybenzoic acid + Hydroquinone R09105 all-<i>trans</i>-octaprenyl diphosphate + 4-Hydroxybenzoic acid > Pyrophosphate + 3-Octaprenyl-4-hydroxybenzoate 4OHBENZOATE-OCTAPRENYLTRANSFER-RXN Chorismate > 4-Hydroxybenzoic acid + Pyruvic acid R01302 CHORPYRLY-RXN 4-Hydroxybenzoic acid + Octaprenyl diphosphate > 3-Octaprenyl-4-hydroxybenzoate 4-Hydroxybenzoic acid + Octaprenyl diphosphate + Octaprenyl diphosphate > Pyrophosphate + 3-Octaprenyl-4-hydroxybenzoate PW_R003716 4 4-Hydroxybenzoic acid + Octaprenyl diphosphate >3 3-Octaprenyl-4-hydroxybenzoate + Pyrophosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 52.2 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 208800 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 787.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 3148000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 294.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 1176000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621