2.02012-05-31 10:26:28 -06002015-09-13 12:56:08 -0600ECMDB00375M2MDB0001333-(3-Hydroxyphenyl)propanoic acid3-(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)-propanoate3-(3-Hydroxy-phenyl)-propanoic acid3-(3-Hydroxy-phenyl)-propionate3-(3-hydroxy-phenyl)-propionic acid3-(3-Hydroxyphenyl)propanoate3-(3-Hydroxyphenyl)propanoic acid3-(3-Hydroxyphenyl)propionate3-(3-Hydroxyphenyl)propionic acid3-(m-Hydroxyphenyl)propionate3-(m-Hydroxyphenyl)propionic acid3-Hydroxybenzenepropanoate3-Hydroxybenzenepropanoic acid3-Hydroxydihydrocinnamate3-Hydroxydihydrocinnamic acid3-Hydroxyhydrocinnamate3-hydroxyhydrocinnamic acid3-Hydroxyphenylpropanoate3-Hydroxyphenylpropanoic acid3-Hydroxyphenylpropionate3-Hydroxyphenylpropionic acidB-(3-Hydroxyphenyl)propionateB-(3-Hydroxyphenyl)propionic acidB-(m-Hydroxyphenyl)propionateB-(m-Hydroxyphenyl)propionic acidBeta-(3-Hydroxyphenyl)propionateBeta-(3-Hydroxyphenyl)propionic acidBeta-(m-Hydroxyphenyl)propionateBeta-(m-Hydroxyphenyl)propionic aciddihydro-3-CoumarateDihydro-3-coumaric acidDihydro-m-coumarateDihydro-m-coumaric acidm-HydrocoumarateM-hydrocoumaric acidM-Hydroxy-HydrocinnamateM-Hydroxy-Hydrocinnamic acidM-HydroxyphenylpropionateM-Hydroxyphenylpropionic acidβ-(3-Hydroxyphenyl)propionateβ-(3-Hydroxyphenyl)propionic acidβ-(m-Hydroxyphenyl)propionateβ-(m-Hydroxyphenyl)propionic acidC9H10O3166.1739166.0629941863-(3-hydroxyphenyl)propanoic acid3-hydroxyphenylpropionic acid621-54-5OC(=O)CCC1=CC=CC(O)=C1InChI=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-NCytosolExtra-organismPeriplasmlogp1.14logs-1.77solubility2.80e+00 g/llogp1.75pka_strongest_acidic4.21pka_strongest_basic-6iupac3-(3-hydroxyphenyl)propanoic acidaverage_mass166.1739mono_mass166.062994186smilesOC(=O)CCC1=CC=CC(O)=C1formulaC9H10O3inchiInChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)inchikeyQVWAEZJXDYOKEH-UHFFFAOYSA-Npolar_surface_area57.53refractivity43.95polarizability16.92rotatable_bond_count3acceptor_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.PW000921ec00360MetabolicMicrobial metabolism in diverse environmentsec011202-Oxopent-4-enoate metabolismThe 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 cyclePW001890Metabolic2-Oxopent-4-enoate metabolism 2The 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 cyclePW002035MetabolicSpecdb::CMs5608Specdb::CMs29889Specdb::CMs31859Specdb::CMs37477Specdb::CMs99566Specdb::CMs99567Specdb::CMs155067Specdb::CMs1059869Specdb::CMs1059871Specdb::CMs1059872Specdb::CMs1059874Specdb::CMs1059876Specdb::NmrOneD143690Specdb::NmrOneD143691Specdb::NmrOneD143692Specdb::NmrOneD143693Specdb::NmrOneD143694Specdb::NmrOneD143695Specdb::NmrOneD143696Specdb::NmrOneD143697Specdb::NmrOneD143698Specdb::NmrOneD143699Specdb::NmrOneD143700Specdb::NmrOneD143701Specdb::NmrOneD143702Specdb::NmrOneD143703Specdb::NmrOneD143704Specdb::NmrOneD143705Specdb::NmrOneD143706Specdb::NmrOneD143707Specdb::NmrOneD143708Specdb::NmrOneD143709Specdb::MsMs26690Specdb::MsMs26691Specdb::MsMs26692Specdb::MsMs33248Specdb::MsMs33249Specdb::MsMs33250Specdb::MsMs2252852Specdb::MsMs2253606Specdb::MsMs2254967Specdb::MsMs2255632Specdb::MsMs2811599Specdb::MsMs2811600Specdb::MsMs2811601Specdb::MsMs2894726Specdb::MsMs2894727Specdb::MsMs2894728HMDB0037589C114571427Keseler, I. 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A., Williamson, G., Scalbert, A. (2003). "Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects." Am J Clin Nutr 77:912-918.12663291Konishi, Y., Kobayashi, S. (2004). "Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers." J Agric Food Chem 52:6418-6424.15479001Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7.10706426Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5.2044590http://hmdb.ca/system/metabolites/msds/000/000/294/original/HMDB00375.pdf?13584612393-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylaseP77397MHPA_ECOLImhpAhttp://ecmdb.ca/proteins/P77397.xmlPutative 3-hydroxyphenylpropionic acid transporterP77589MHPT_ECOLImhpThttp://ecmdb.ca/proteins/P77589.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xml3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NADR067863-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NADR067863-(3-Hydroxyphenyl)propanoic acid + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propanoate + Water + NAD3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-DihydroxycinnamateR06786