2.0 2012-05-31 10:26:28 -0600 2015-09-13 12:56:08 -0600 ECMDB00375 M2MDB000133 3-(3-Hydroxyphenyl)propanoic acid 3-(3-hydroxyphenyl)propanoic acid is a member of the chemical class known as Phenols and Derivatives. Phenols are compounds containing a phenol moiety, which is a benzene bearing an hydroxyl group. 3-(3-hydroxyphenyl)propanoic acid is an intermediate in phenylalanine metabolism pathways. (KEGG) 3-(3-Hydroxy-phenyl)-propanoate 3-(3-Hydroxy-phenyl)-propanoic acid 3-(3-Hydroxy-phenyl)-propionate 3-(3-hydroxy-phenyl)-propionic acid 3-(3-Hydroxyphenyl)propanoate 3-(3-Hydroxyphenyl)propanoic acid 3-(3-Hydroxyphenyl)propionate 3-(3-Hydroxyphenyl)propionic acid 3-(m-Hydroxyphenyl)propionate 3-(m-Hydroxyphenyl)propionic acid 3-Hydroxybenzenepropanoate 3-Hydroxybenzenepropanoic acid 3-Hydroxydihydrocinnamate 3-Hydroxydihydrocinnamic acid 3-Hydroxyhydrocinnamate 3-hydroxyhydrocinnamic acid 3-Hydroxyphenylpropanoate 3-Hydroxyphenylpropanoic acid 3-Hydroxyphenylpropionate 3-Hydroxyphenylpropionic acid B-(3-Hydroxyphenyl)propionate B-(3-Hydroxyphenyl)propionic acid B-(m-Hydroxyphenyl)propionate B-(m-Hydroxyphenyl)propionic acid Beta-(3-Hydroxyphenyl)propionate Beta-(3-Hydroxyphenyl)propionic acid Beta-(m-Hydroxyphenyl)propionate Beta-(m-Hydroxyphenyl)propionic acid dihydro-3-Coumarate Dihydro-3-coumaric acid Dihydro-m-coumarate Dihydro-m-coumaric acid m-Hydrocoumarate M-hydrocoumaric acid M-Hydroxy-Hydrocinnamate M-Hydroxy-Hydrocinnamic acid M-Hydroxyphenylpropionate M-Hydroxyphenylpropionic acid β-(3-Hydroxyphenyl)propionate β-(3-Hydroxyphenyl)propionic acid β-(m-Hydroxyphenyl)propionate β-(m-Hydroxyphenyl)propionic acid C9H10O3 166.1739 166.062994186 3-(3-hydroxyphenyl)propanoic acid 3-hydroxyphenylpropionic acid 621-54-5 OC(=O)CCC1=CC=CC(O)=C1 InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) QVWAEZJXDYOKEH-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp 1.14 ALOGPS logs -1.77 ALOGPS solubility 2.80e+00 g/l ALOGPS logp 1.75 ChemAxon pka_strongest_acidic 4.21 ChemAxon pka_strongest_basic -6 ChemAxon iupac 3-(3-hydroxyphenyl)propanoic acid ChemAxon average_mass 166.1739 ChemAxon mono_mass 166.062994186 ChemAxon smiles OC(=O)CCC1=CC=CC(O)=C1 ChemAxon formula C9H10O3 ChemAxon inchi InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12) ChemAxon inchikey QVWAEZJXDYOKEH-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 43.95 ChemAxon polarizability 16.92 ChemAxon rotatable_bond_count 3 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 Microbial metabolism in diverse environments ec01120 2-Oxopent-4-enoate metabolism The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle PW001890 Metabolic 2-Oxopent-4-enoate metabolism 2 The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle PW002035 Metabolic Specdb::CMs 5608 Specdb::CMs 29889 Specdb::CMs 31859 Specdb::CMs 37477 Specdb::CMs 99566 Specdb::CMs 99567 Specdb::CMs 155067 Specdb::CMs 1059869 Specdb::CMs 1059871 Specdb::CMs 1059872 Specdb::CMs 1059874 Specdb::CMs 1059876 Specdb::NmrOneD 143690 Specdb::NmrOneD 143691 Specdb::NmrOneD 143692 Specdb::NmrOneD 143693 Specdb::NmrOneD 143694 Specdb::NmrOneD 143695 Specdb::NmrOneD 143696 Specdb::NmrOneD 143697 Specdb::NmrOneD 143698 Specdb::NmrOneD 143699 Specdb::NmrOneD 143700 Specdb::NmrOneD 143701 Specdb::NmrOneD 143702 Specdb::NmrOneD 143703 Specdb::NmrOneD 143704 Specdb::NmrOneD 143705 Specdb::NmrOneD 143706 Specdb::NmrOneD 143707 Specdb::NmrOneD 143708 Specdb::NmrOneD 143709 Specdb::MsMs 26690 Specdb::MsMs 26691 Specdb::MsMs 26692 Specdb::MsMs 33248 Specdb::MsMs 33249 Specdb::MsMs 33250 Specdb::MsMs 2252852 Specdb::MsMs 2253606 Specdb::MsMs 2254967 Specdb::MsMs 2255632 Specdb::MsMs 2811599 Specdb::MsMs 2811600 Specdb::MsMs 2811601 Specdb::MsMs 2894726 Specdb::MsMs 2894727 Specdb::MsMs 2894728 HMDB00375 89 C11457 1427 Keseler, I. 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Eur J Pediatr. 1991 Jan;150(3):190-5. 2044590 http://hmdb.ca/system/metabolites/msds/000/000/294/original/HMDB00375.pdf?1358461239 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase P77397 MHPA_ECOLI mhpA http://ecmdb.ca/proteins/P77397.xml Putative 3-hydroxyphenylpropionic acid transporter P77589 MHPT_ECOLI mhpT http://ecmdb.ca/proteins/P77589.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml 3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD R06786 3-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD R06786 3-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD 3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-Dihydroxycinnamate R06786