2.0 2012-07-30 14:54:45 -0600 2015-09-13 12:56:14 -0600 ECMDB21171 M2MDB001580 3-Hydroxycinnamic acid 3-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 acid 3'-Hydroxycinnamate 3'-Hydroxycinnamic acid 3-(3-Hydroxyphenyl)-2-Propenoate 3-(3-Hydroxyphenyl)-2-Propenoic acid 3-(3-Hydroxyphenyl)acrylate 3-(3-Hydroxyphenyl)acrylic acid 3-(3-Hydroxyphenyl)acrylsaeure 3-(3-Hydroxyphenyl)prop-2-enoate 3-(3-Hydroxyphenyl)prop-2-enoic acid 3-Coumarate 3-Coumaric acid 3-Hydroxycinnamate 3-Hydroxycinnamic acid M-Coumarate M-Coumaric acid M-Hydroxy-Cinnamate M-Hydroxy-Cinnamic acid M-Hydroxycinnamate M-Hydroxycinnamic acid Trans-3-Coumarate Trans-3-Coumaric acid Trans-3-Hydroxycinnamate Trans-3-Hydroxycinnamic acid C9H8O3 164.158 164.047344122 (2E)-3-(3-hydroxyphenyl)prop-2-enoic acid m-coumaric acid 588-30-7 OC(=O)\C=C\C1=CC=CC(O)=C1 InChI=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-N Solid Cytosol Extra-organism Periplasm logp 1.71 ALOGPS logs -2.20 ALOGPS solubility 1.04e+00 g/l ALOGPS melting_point 192-194 oC logp 1.83 ChemAxon pka_strongest_acidic 4.01 ChemAxon pka_strongest_basic -6 ChemAxon iupac (2E)-3-(3-hydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 164.158 ChemAxon mono_mass 164.047344122 ChemAxon smiles OC(=O)\C=C\C1=CC=CC(O)=C1 ChemAxon formula C9H8O3 ChemAxon inchi InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ ChemAxon inchikey KKSDGJDHHZEWEP-SNAWJCMRSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 45.04 ChemAxon polarizability 16.37 ChemAxon rotatable_bond_count 2 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 cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690 Specdb::CMs 1588 Specdb::CMs 6004 Specdb::CMs 31350 Specdb::CMs 31835 Specdb::CMs 38137 Specdb::CMs 171374 Specdb::EiMs 1965 Specdb::NmrOneD 1743 Specdb::MsMs 1675 Specdb::MsMs 1676 Specdb::MsMs 1677 Specdb::MsMs 5442 Specdb::MsMs 5443 Specdb::MsMs 241516 Specdb::MsMs 241517 Specdb::MsMs 241518 Specdb::MsMs 243571 Specdb::MsMs 243572 Specdb::MsMs 243573 Specdb::MsMs 439203 Specdb::MsMs 439204 Specdb::MsMs 2236075 Specdb::MsMs 2236111 Specdb::MsMs 2237279 Specdb::MsMs 2237291 Specdb::MsMs 2238176 Specdb::MsMs 2238244 Specdb::MsMs 2239320 Specdb::MsMs 2239415 Specdb::MsMs 2240269 Specdb::MsMs 2240289 Specdb::MsMs 2240337 Specdb::MsMs 2241402 Specdb::NmrTwoD 1086 Specdb::NmrTwoD 1683 HMDB01713 637541 553147 C12621 47925 CPD-10797 Keseler, I. 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Br J Nutr. 2006 Jul;96(1):191-8. 16870009 http://hmdb.ca/system/metabolites/msds/000/001/428/original/HMDB01713.pdf?1358463096 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-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + Water + NAD R06787 RXN-10040 3-Hydroxycinnamic acid + Oxygen + NADH + Hydrogen ion <> Trans-2,3-Dihydroxycinnamate + Water + NAD R06787 3-Hydroxycinnamic acid + NADH + Oxygen > Trans-2,3-Dihydroxycinnamate + 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 3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > NAD + Water + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid PW_R005155