2.0 2015-09-18 17:30:02 -0600 2015-09-18 17:30:02 -0600 ECMDB24915 M2MDB007032 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid C9H8O4 180.1574 180.042258744 (2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid 4,α-dihydroxycinnamic acid OC(=O)C(\O)=C\C1=CC=C(O)C=C1 InChI=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-N logp 1.28 ALOGPS logs -2.35 ALOGPS solubility 8.14e-01 g/l ALOGPS logp 1.31 ChemAxon pka_strongest_acidic 3.16 ChemAxon pka_strongest_basic -6 ChemAxon iupac (2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid ChemAxon average_mass 180.1574 ChemAxon mono_mass 180.042258744 ChemAxon smiles OC(=O)C(\O)=C\C1=CC=C(O)C=C1 ChemAxon formula C9H8O4 ChemAxon inchi InChI=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- ChemAxon inchikey GQYBCIHRWMPOOF-YVMONPNESA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 47.01 ChemAxon polarizability 17.25 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon 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 16828 Specdb::CMs 39139 Specdb::CMs 166292 Specdb::NmrOneD 288235 Specdb::NmrOneD 288236 Specdb::NmrOneD 288237 Specdb::NmrOneD 288238 Specdb::NmrOneD 288239 Specdb::NmrOneD 288240 Specdb::NmrOneD 288241 Specdb::NmrOneD 288242 Specdb::NmrOneD 288243 Specdb::NmrOneD 288244 Specdb::NmrOneD 288245 Specdb::NmrOneD 288246 Specdb::NmrOneD 288247 Specdb::NmrOneD 288248 Specdb::NmrOneD 288249 Specdb::NmrOneD 288250 Specdb::NmrOneD 288251 Specdb::NmrOneD 288252 Specdb::NmrOneD 288253 Specdb::NmrOneD 288254 Specdb::MsMs 303190 Specdb::MsMs 303191 Specdb::MsMs 303192 Specdb::MsMs 346087 Specdb::MsMs 346088 Specdb::MsMs 346089 Specdb::MsMs 2401043 Specdb::MsMs 2401044 Specdb::MsMs 2401045 Specdb::MsMs 2538107 Specdb::MsMs 2538108 Specdb::MsMs 2538109 2,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenase P0ABR9 MHPB_ECOLI mhpB http://ecmdb.ca/proteins/P0ABR9.xml 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase P0CI31 hcaB http://ecmdb.ca/proteins/P0CI31.xml 3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylase P77397 MHPA_ECOLI mhpA http://ecmdb.ca/proteins/P77397.xml 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 NAD + 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 acid PW_R005157 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + Oxygen + 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid > Hydrogen ion + 2-Hydroxy-6-ketononatrienedioate PW_R005158 Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid + NADH + Hydrogen ion PW_R005946