2.02012-05-31 10:27:02 -06002015-09-13 12:56:08 -0600ECMDB00500M2MDB0001434-Hydroxybenzoic acid4-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-Carboxyphenol4-Hydroxy-benzoate4-Hydroxy-benzoesaeure4-Hydroxy-benzoic acid4-Hydroxybenzoate4-Hydroxybenzoic acid<i>p</i>-hydroxybenzoateP-CarboxyphenolP-Hydroxy-BenzoateP-Hydroxy-Benzoic acidP-HydroxybenzoateP-Hydroxybenzoic acidP-SalicylateP-Salicylic acidParaben-acidPHBAC7H6O3138.1207138.0316940584-hydroxybenzoic acidP-hydroxybenzoic acid99-96-7OC(=O)C1=CC=C(O)C=C1InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)FJKROLUGYXJWQN-UHFFFAOYSA-NSolidCytosollogp1.58logs-1.06solubility1.19e+01 g/llogp1.33pka_strongest_acidic4.38pka_strongest_basic-6.1iupac4-hydroxybenzoic acidaverage_mass138.1207mono_mass138.031694058smilesOC(=O)C1=CC=C(O)C=C1formulaC7H6O3inchiInChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)inchikeyFJKROLUGYXJWQN-UHFFFAOYSA-Npolar_surface_area57.53refractivity35.3polarizability12.94rotatable_bond_count1acceptor_count3donor_count2physiological_charge-1formal_charge0Phenylalanine metabolismThe 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.PW000921ec00360MetabolicUbiquinone and other terpenoid-quinone biosynthesisec00130Benzoate degradation via hydroxylationec003621,4-Dichlorobenzene degradationec00627Microbial metabolism in diverse environmentsec01120Toluene degradationec00623Bisphenol degradationec00363Metabolic pathwayseco01100Secondary Metabolites: Ubiquinol biosynthesisThe 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.
PW000981MetabolicSecondary Metabolites: Ubiquinol biosynthesis 2The 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.PW002036MetabolicSpecdb::CMs562Specdb::CMs563Specdb::CMs564Specdb::CMs1306Specdb::CMs3055Specdb::CMs27535Specdb::CMs29091Specdb::CMs29550Specdb::CMs29661Specdb::CMs29780Specdb::CMs30128Specdb::CMs30329Specdb::CMs30670Specdb::CMs30925Specdb::CMs31155Specdb::CMs31881Specdb::CMs37574Specdb::CMs161901Specdb::CMs1064187Specdb::CMs1064189Specdb::CMs1064191Specdb::CMs1064192Specdb::CMs1064194Specdb::EiMs1592Specdb::NmrOneD1394Specdb::NmrOneD4014Specdb::NmrOneD4301Specdb::NmrOneD4898Specdb::NmrOneD4899Specdb::NmrOneD6942Specdb::NmrOneD6943Specdb::NmrOneD6944Specdb::NmrOneD6945Specdb::NmrOneD6946Specdb::NmrOneD6947Specdb::NmrOneD6948Specdb::NmrOneD6949Specdb::NmrOneD6950Specdb::NmrOneD6951Specdb::NmrOneD6952Specdb::NmrOneD6953Specdb::NmrOneD6954Specdb::NmrOneD6955Specdb::NmrOneD6956Specdb::NmrOneD6957Specdb::NmrOneD6958Specdb::NmrOneD6959Specdb::NmrOneD6960Specdb::NmrOneD6961Specdb::MsMs716Specdb::MsMs717Specdb::MsMs718Specdb::MsMs4111Specdb::MsMs4112Specdb::MsMs4113Specdb::MsMs4114Specdb::MsMs4115Specdb::MsMs4116Specdb::MsMs4117Specdb::MsMs4118Specdb::MsMs4122Specdb::MsMs4123Specdb::MsMs4124Specdb::MsMs179391Specdb::MsMs179392Specdb::MsMs179393Specdb::MsMs181719Specdb::MsMs181720Specdb::MsMs181721Specdb::MsMs374047Specdb::MsMs437771Specdb::MsMs437772Specdb::MsMs437773Specdb::MsMs437774Specdb::NmrTwoD1021Specdb::NmrTwoD1338HMDB00500135132C00156307634-hydroxybenzoatePHB4-Hydroxybenzoic acidKeseler, 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?1358461253Chorismate--pyruvate lyaseP26602UBIC_ECOLIubiChttp://ecmdb.ca/proteins/P26602.xml4-hydroxybenzoate octaprenyltransferaseP0AGK1UBIA_ECOLIubiAhttp://ecmdb.ca/proteins/P0AGK1.xmlacetyl esterase (EC:3.1.1.-)P23872aeshttp://ecmdb.ca/proteins/P23872.xmlChorismate <> 4-Hydroxybenzoic acid + Pyruvic acidR01302CHORPYRLY-RXN4-Hydroxybenzoic acid + Octaprenyl diphosphate > 3-Octaprenyl-4-hydroxybenzoate + PyrophosphateR056154-Hydroxybenzoic acid + Pyruvic acid <> ChorismateR01302all-trans-Polyprenyl diphosphate + 4-Hydroxybenzoic acid + Geranyl-PP <> 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate + 4-Hydroxy-3-polyprenylbenzoateR05000Octaprenyl diphosphate + 4-Hydroxybenzoic acid <> 3-Octaprenyl-4-hydroxybenzoate + PyrophosphateR056154-Hydroxyphenyl-4-hydroxybenzoate + Water <> 4-Hydroxybenzoic acid + HydroquinoneR09105all-<i>trans</i>-octaprenyl diphosphate + 4-Hydroxybenzoic acid > Pyrophosphate + 3-Octaprenyl-4-hydroxybenzoate4OHBENZOATE-OCTAPRENYLTRANSFER-RXNChorismate > 4-Hydroxybenzoic acid + Pyruvic acidR01302CHORPYRLY-RXN4-Hydroxybenzoic acid + Octaprenyl diphosphate > 3-Octaprenyl-4-hydroxybenzoate4-Hydroxybenzoic acid + Octaprenyl diphosphate + Octaprenyl diphosphate > Pyrophosphate + 3-Octaprenyl-4-hydroxybenzoatePW_R0037164 4-Hydroxybenzoic acid + Octaprenyl diphosphate >3 3-Octaprenyl-4-hydroxybenzoate + PyrophosphateGutnick 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 glucoseShake flask and filter culture52.2uM0.037 oCK12 NCM3722Mid-Log Phase2088000Bennett, 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 5:593-599.19561621Gutnick 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 glycerolShake flask and filter culture787.0uM0.037 oCK12 NCM3722Mid-Log Phase31480000Bennett, 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 5:593-599.19561621Gutnick 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 acetateShake flask and filter culture294.0uM0.037 oCK12 NCM3722Mid-Log Phase11760000Bennett, 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