2.0 2012-07-30 14:55:23 -0600 2015-09-13 12:56:15 -0600 ECMDB21349 M2MDB001747 p-Cresol p-Cresol, also known as 4-methylphenol or 4-hydroxytoluene, is a positional isomer of cresol. The other two isomers are m-cresol and o-cresol. (Wikipedia) p-Cresol is one of the metabolites of the amino acid tyrosine, and to a certain extent also of phenylalanine, which are converted to 4-hydroxyphenylacetic acid by intestinal bacteria, before being decarboxylated to p-cresol (putrefaction). The main contributing bacteria are aerobes (mainly enterobacteria), but to a certain extent also anaerobes play a role (mainly Clostridium perfringens). p-Cresol has been reported to affect several biochemical, biological and physiological functions: for example, it alters cell membrane permeability in bacteria. (HMDB, PMID 10570076) In E. coli, p-Cresol can be produced as a by-product of thiazole biosynthesis. (EcoCyc) 1-Hydroxy-4-methylbenzene 1-Methyl-4-hydroxybenzene 4-(Pentafluorosulfanyl)phenol 4-(Pentafluorosulphanyl)phenol 4-Cresol 4-Hydroxytoluene 4-methyl phenol 4-Methyl-Phenol 4-Methylphenol 4-Methylphenol ( p-cresol) <i>p</i>-cresol Cresol, para P-Cresol P-Cresol (4-methylphenol) P-Cresol 98+ % P-Cresol for synthesis P-Cresol Hydrate 90 % P-Cresol Hydric acid 90 % P-Cresylate P-Cresylic acid P-Hydroxytoluene P-Kresol P-Methyl phenol P-Methylhydroxybenzene P-Methylphenol P-Oxytoluene P-Toluol P-Tolyl alcohol Paracresol Paramethyl phenol Phenol, 4-methyI C7H8O 108.1378 108.057514878 4-methylphenol P-cresol 106-44-5 CC1=CC=C(O)C=C1 InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 IWDCLRJOBJJRNH-UHFFFAOYSA-N Solid Cytosol Membrane logp 1.95 ALOGPS logs -0.67 ALOGPS solubility 2.31e+01 g/l ALOGPS melting_point 35.5 oC logp 2.18 ChemAxon pka_strongest_acidic 10.36 ChemAxon pka_strongest_basic -5.4 ChemAxon iupac 4-methylphenol ChemAxon average_mass 108.1378 ChemAxon mono_mass 108.057514878 ChemAxon smiles CC1=CC=C(O)C=C1 ChemAxon formula C7H8O ChemAxon inchi InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3 ChemAxon inchikey IWDCLRJOBJJRNH-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 33.08 ChemAxon polarizability 11.93 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Thiamine metabolism ec00730 Metabolic pathways eco01100 tyrosine biosynthesis The pathways of biosynthesis of phenylalaline and tyrosine are intimately connected. First step of both pathways is the conversion of chorismate to prephenate, the third step of both is the conversion of a ketoacid to the aminoacid through transamination. The two pathways differ only in the second step of their three-step reaction sequences: In the case of phenylalanine biosynthesi a dehydratase converts prephenate to phenylpyruvate(reaction occurs slowly in the absence of enzymic activity); in the case of tyrosine biosynthesis, a dehydrogenase converts prephenate to p-hydroxyphenylpyruvate. Also in both pathways the first two steps are catalyzed by two distinc active sites on a single protein. Thus the first step of each pathway can be catalyzed by two enzyme: those associated with both the phenylalanine specific dehydratase and the tyrosine specific dehydrogenase. 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 PW000806 Metabolic thiazole biosynthesis I (E. coli) PWY-6892 Specdb::CMs 3422 Specdb::CMs 26739 Specdb::CMs 26989 Specdb::CMs 27770 Specdb::CMs 29484 Specdb::CMs 31780 Specdb::CMs 38149 Specdb::CMs 99708 Specdb::CMs 99709 Specdb::CMs 99710 Specdb::CMs 99711 Specdb::CMs 99712 Specdb::CMs 131518 Specdb::CMs 139252 Specdb::EiMs 129 Specdb::NmrOneD 1760 Specdb::NmrOneD 2089 Specdb::NmrOneD 2783 Specdb::NmrOneD 5117 Specdb::NmrOneD 5118 Specdb::MsMs 1729 Specdb::MsMs 1730 Specdb::MsMs 1731 Specdb::MsMs 5493 Specdb::MsMs 5494 Specdb::MsMs 5495 Specdb::MsMs 5496 Specdb::MsMs 180147 Specdb::MsMs 180148 Specdb::MsMs 180149 Specdb::MsMs 182481 Specdb::MsMs 182482 Specdb::MsMs 182483 Specdb::MsMs 1471225 Specdb::MsMs 2740414 Specdb::MsMs 2740415 Specdb::MsMs 2740416 Specdb::MsMs 2937874 Specdb::MsMs 2937875 Specdb::MsMs 2937876 Specdb::NmrTwoD 1700 HMDB01858 2879 13839082 C01468 17847 CPD-108 PCR P-Cresol Keseler, I. 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Adv Ren Replace Ther. 2003 Oct;10(4):310-20. 14681860 http://hmdb.ca/system/metabolites/msds/000/001/449/original/HMDB01858.pdf?1358461771 Thiazole synthase P30139 THIG_ECOLI thiG http://ecmdb.ca/proteins/P30139.xml Dehydroglycine synthase P30140 THIH_ECOLI thiH http://ecmdb.ca/proteins/P30140.xml S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion RXN-11319 L-Tyrosine + S-adenosyl-L-methionine + reduced acceptor > 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + acceptor +2 Hydrogen ion L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion R10246 L-Tyrosine + NADPH + S-adenosyl-L-methionine + L-Tyrosine + NADPH > Hydrogen ion + NADP + L-Methionine + 5'-Deoxyadenosine + p-Cresol + 2-iminoacetate PW_R005174