2.0 2012-05-31 14:24:34 -0600 2015-07-07 12:14:59 -0600 ECMDB20045 M2MDB000894 2-Maleylacetate 2-maleylacetate belongs to the class of Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. (inferred from compound structure)<br/><br/>2-Maleylacetate is involved in the degradation pathway of aromatic compounds. Reduction of the double bond in maleylacetate is catalyzed by the enzyme maleylacetate reductase, which was also purified from E. coli (PMID 8900023) (2Z)-4-oxohex-2-enedioate (2Z)-4-oxohex-2-enedioic acid (Z)-4-oxo-2-hexenedioate (Z)-4-oxo-2-hexenedioic acid 2-Maleylacetic acid 4-Oxo-(Z)-2-Hexenedioate 4-Oxo-(Z)-2-Hexenedioic acid 4-Oxohex-2-enedioate 4-Oxohex-2-enedioic acid Maleoylacetate Maleoylacetic acid Maleylacetate Maleylacetic acid C6H6O5 158.1088 158.021523302 (2Z)-4-oxohex-2-enedioic acid maleylacetic acid 24740-88-3 OC(=O)CC(=O)\C=C/C(O)=O InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1- SOXXPQLIZIPMIZ-UPHRSURJSA-N Outer membrane Inner membrane logp -0.06 ALOGPS logs -1.34 ALOGPS solubility 7.25e+00 g/l ALOGPS logp 0.18 ChemAxon pka_strongest_acidic 2.71 ChemAxon pka_strongest_basic -7.2 ChemAxon iupac (2Z)-4-oxohex-2-enedioic acid ChemAxon average_mass 158.1088 ChemAxon mono_mass 158.021523302 ChemAxon smiles OC(=O)CC(=O)\C=C/C(O)=O ChemAxon formula C6H6O5 ChemAxon inchi InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1- ChemAxon inchikey SOXXPQLIZIPMIZ-UPHRSURJSA-N ChemAxon polar_surface_area 91.67 ChemAxon refractivity 34.5 ChemAxon polarizability 13.16 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon gamma-Hexachlorocyclohexane degradation ec00361 Benzoate degradation via hydroxylation ec00362 1,4-Dichlorobenzene degradation ec00627 Fluorobenzoate degradation one step conversion of fluoromuconolactone (5-fluoromuconolactone and 4-fluoromuconolactone ) into maleylactate in order to be degraded following the benzoate degradation This pathway is under revision PW000766 ec00364 Metabolic Microbial metabolism in diverse environments ec01120 Toluene degradation ec00623 Metabolic pathways eco01100 Collection of Reactions without pathways PW001891 Metabolic Specdb::CMs 2981 Specdb::CMs 48147 Specdb::CMs 174083 Specdb::NmrOneD 57492 Specdb::NmrOneD 57493 Specdb::NmrOneD 57494 Specdb::NmrOneD 57495 Specdb::NmrOneD 57496 Specdb::NmrOneD 57497 Specdb::NmrOneD 57498 Specdb::NmrOneD 57499 Specdb::NmrOneD 57500 Specdb::NmrOneD 57501 Specdb::NmrOneD 57502 Specdb::NmrOneD 57503 Specdb::NmrOneD 57504 Specdb::NmrOneD 57505 Specdb::NmrOneD 57506 Specdb::NmrOneD 57507 Specdb::NmrOneD 57508 Specdb::NmrOneD 57509 Specdb::NmrOneD 57510 Specdb::NmrOneD 57511 Specdb::MsMs 25361 Specdb::MsMs 25362 Specdb::MsMs 25363 Specdb::MsMs 31919 Specdb::MsMs 31920 Specdb::MsMs 31921 Specdb::MsMs 3225088 Specdb::MsMs 3225089 Specdb::MsMs 3225090 Specdb::MsMs 3225091 Specdb::MsMs 3225092 Specdb::MsMs 3225093 5280500 C02222 1184 CPD-294 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Putative carboxymethylenebutenolidase P56262 DLHH_ECOLI ysgA http://ecmdb.ca/proteins/P56262.xml acetyl esterase (EC:3.1.1.-) P23872 aes http://ecmdb.ca/proteins/P23872.xml Cis-4-Carboxymethylenebut-2-en-4-olide + Water <> 2-Maleylacetate R03893 4-Sulfolactone + Water <> HSO3- + 2-Maleylacetate + Hydrogen ion R05420 Trans-4-Carboxymethylenebut-2-en-4-olide + Water <> 2-Maleylacetate R06838 5-Fluoromuconolactone + Water <> 2-Maleylacetate + Hydrofluoric acid R08120 4-Fluoromuconolactone + Water <> 2-Maleylacetate + Hydrofluoric acid R08121 Hydrofluoric acid + Water > 2-Maleylacetate + hydrofluoric acid PW_R005891 5-Fluoromuconolactone + Water > 2-Maleylacetate + hydrofluoric acid PW_R005892