2.02015-09-18 17:30:02 -06002015-09-18 17:30:02 -0600ECMDB24915M2MDB0070322-Hydroxy-3-(4-hydroxyphenyl)propenoic acidC9H8O4180.1574180.042258744(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid4,α-dihydroxycinnamic acidOC(=O)C(\O)=C\C1=CC=C(O)C=C1InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-GQYBCIHRWMPOOF-YVMONPNESA-Nlogp1.28logs-2.35solubility8.14e-01 g/llogp1.31pka_strongest_acidic3.16pka_strongest_basic-6iupac(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acidaverage_mass180.1574mono_mass180.042258744smilesOC(=O)C(\O)=C\C1=CC=C(O)C=C1formulaC9H8O4inchiInChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-inchikeyGQYBCIHRWMPOOF-YVMONPNESA-Npolar_surface_area77.76refractivity47.01polarizability17.25rotatable_bond_count2acceptor_count4donor_count3physiological_charge-1formal_charge02-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::CMs16828Specdb::CMs39139Specdb::CMs166292Specdb::NmrOneD288235Specdb::NmrOneD288236Specdb::NmrOneD288237Specdb::NmrOneD288238Specdb::NmrOneD288239Specdb::NmrOneD288240Specdb::NmrOneD288241Specdb::NmrOneD288242Specdb::NmrOneD288243Specdb::NmrOneD288244Specdb::NmrOneD288245Specdb::NmrOneD288246Specdb::NmrOneD288247Specdb::NmrOneD288248Specdb::NmrOneD288249Specdb::NmrOneD288250Specdb::NmrOneD288251Specdb::NmrOneD288252Specdb::NmrOneD288253Specdb::NmrOneD288254Specdb::MsMs303190Specdb::MsMs303191Specdb::MsMs303192Specdb::MsMs346087Specdb::MsMs346088Specdb::MsMs346089Specdb::MsMs2401043Specdb::MsMs2401044Specdb::MsMs2401045Specdb::MsMs2538107Specdb::MsMs2538108Specdb::MsMs25381092,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenaseP0ABR9MHPB_ECOLImhpBhttp://ecmdb.ca/proteins/P0ABR9.xml3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenaseP0CI31hcaBhttp://ecmdb.ca/proteins/P0CI31.xml3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylaseP77397MHPA_ECOLImhpAhttp://ecmdb.ca/proteins/P77397.xml3-Hydroxycinnamic acid + Hydrogen ion + NADH + Oxygen > NAD + Water + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidPW_R005155NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol > NADH + Hydrogen ion + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acidPW_R0051572-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + Oxygen + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioatePW_R005158Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + NADH + Hydrogen ionPW_R005946