2.02012-07-30 14:54:45 -06002015-09-13 12:56:14 -0600ECMDB21171M2MDB0015803-Hydroxycinnamic acid3-hydroxycinnamic acid, also known as m-coumaric acid, is an aromatic acid. Research has shown that E. coli K-12 can grow with 3-hydroxycinnamic acid as the sole carbon source. (EcoCyc, PMID 6345502)(2<i>E</i>)-3-(3-hydroxyphenyl)prop-2-enoate(2E)-3-(3-hydroxyphenyl)-2-propenoate(2E)-3-(3-hydroxyphenyl)-2-propenoic acid(2E)-3-(3-hydroxyphenyl)acrylate(2E)-3-(3-hydroxyphenyl)acrylic acid(2E)-3-(3-hydroxyphenyl)prop-2-enoate(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid(E)-3-(3-hydroxyphenyl)-2-propenoate(E)-3-(3-hydroxyphenyl)-2-propenoic acid3'-Hydroxycinnamate3'-Hydroxycinnamic acid3-(3-Hydroxyphenyl)-2-Propenoate3-(3-Hydroxyphenyl)-2-Propenoic acid3-(3-Hydroxyphenyl)acrylate3-(3-Hydroxyphenyl)acrylic acid3-(3-Hydroxyphenyl)acrylsaeure3-(3-Hydroxyphenyl)prop-2-enoate3-(3-Hydroxyphenyl)prop-2-enoic acid3-Coumarate3-Coumaric acid3-Hydroxycinnamate3-Hydroxycinnamic acidM-CoumarateM-Coumaric acidM-Hydroxy-CinnamateM-Hydroxy-Cinnamic acidM-HydroxycinnamateM-Hydroxycinnamic acidTrans-3-CoumarateTrans-3-Coumaric acidTrans-3-HydroxycinnamateTrans-3-Hydroxycinnamic acidC9H8O3164.158164.047344122(2E)-3-(3-hydroxyphenyl)prop-2-enoic acidm-coumaric acid588-30-7OC(=O)\C=C\C1=CC=CC(O)=C1InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+KKSDGJDHHZEWEP-SNAWJCMRSA-NSolidCytosolExtra-organismPeriplasmlogp1.71logs-2.20solubility1.04e+00 g/lmelting_point192-194 oClogp1.83pka_strongest_acidic4.01pka_strongest_basic-6iupac(2E)-3-(3-hydroxyphenyl)prop-2-enoic acidaverage_mass164.158mono_mass164.047344122smilesOC(=O)\C=C\C1=CC=CC(O)=C1formulaC9H8O3inchiInChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+inchikeyKKSDGJDHHZEWEP-SNAWJCMRSA-Npolar_surface_area57.53refractivity45.04polarizability16.37rotatable_bond_count2acceptor_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 cyclePW002035Metaboliccinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoatePWY-6690Specdb::CMs1588Specdb::CMs6004Specdb::CMs31350Specdb::CMs31835Specdb::CMs38137Specdb::CMs171374Specdb::EiMs1965Specdb::NmrOneD1743Specdb::MsMs1675Specdb::MsMs1676Specdb::MsMs1677Specdb::MsMs5442Specdb::MsMs5443Specdb::MsMs241516Specdb::MsMs241517Specdb::MsMs241518Specdb::MsMs243571Specdb::MsMs243572Specdb::MsMs243573Specdb::MsMs439203Specdb::MsMs439204Specdb::MsMs2236075Specdb::MsMs2236111Specdb::MsMs2237279Specdb::MsMs2237291Specdb::MsMs2238176Specdb::MsMs2238244Specdb::MsMs2239320Specdb::MsMs2239415Specdb::MsMs2240269Specdb::MsMs2240289Specdb::MsMs2240337Specdb::MsMs2241402Specdb::NmrTwoD1086Specdb::NmrTwoD1683HMDB01713637541553147C1262147925CPD-10797Keseler, I. 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Br J Nutr. 2006 Jul;96(1):191-8.16870009http://hmdb.ca/system/metabolites/msds/000/001/428/original/HMDB01713.pdf?13584630963-(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-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NADR06787RXN-100403-Hydroxycinnamic acid + Oxygen + NADH + Hydrogen ion <> Trans-2,3-Dihydroxycinnamate + Water + NADR067873-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + 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 3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > NAD + Water + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidPW_R005155