2.0 2012-08-03 14:57:54 -0600 2015-09-13 15:15:32 -0600 ECMDB21397 M2MDB001792 Citraconic acid Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction. (Z)-2-Methyl-2-butenedioate (Z)-2-Methyl-2-butenedioic acid Citraconate Methylmaleate Methylmaleic acid C5H6O4 130.0987 130.02660868 (2Z)-2-methylbut-2-enedioic acid citraconic acid 498-23-7 C\C(=C\C(O)=O)C(O)=O InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2- HNEGQIOMVPPMNR-IHWYPQMZSA-N Solid Cytoplasm logp 0.21 ALOGPS logs -0.91 ALOGPS solubility 1.59e+01 g/l ALOGPS melting_point 88-94 oC logp 0.35 ChemAxon pka_strongest_acidic 2.5 ChemAxon iupac (2Z)-2-methylbut-2-enedioic acid ChemAxon average_mass 130.0987 ChemAxon mono_mass 130.02660868 ChemAxon smiles C\C(=C\C(O)=O)C(O)=O ChemAxon formula C5H6O4 ChemAxon inchi InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2- ChemAxon inchikey HNEGQIOMVPPMNR-IHWYPQMZSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 28.96 ChemAxon polarizability 11.17 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1065 Specdb::CMs 8904 Specdb::CMs 29814 Specdb::CMs 31178 Specdb::CMs 31870 Specdb::CMs 37663 Specdb::CMs 159272 Specdb::CMs 1070803 Specdb::CMs 1070805 Specdb::CMs 1070806 Specdb::CMs 1070808 Specdb::CMs 1070810 Specdb::NmrOneD 1447 Specdb::NmrOneD 20542 Specdb::NmrOneD 20543 Specdb::NmrOneD 20544 Specdb::NmrOneD 20545 Specdb::NmrOneD 20546 Specdb::NmrOneD 20547 Specdb::NmrOneD 20548 Specdb::NmrOneD 20549 Specdb::NmrOneD 20550 Specdb::NmrOneD 20551 Specdb::NmrOneD 20552 Specdb::NmrOneD 20553 Specdb::NmrOneD 20554 Specdb::NmrOneD 20555 Specdb::NmrOneD 20556 Specdb::NmrOneD 20557 Specdb::NmrOneD 20558 Specdb::NmrOneD 20559 Specdb::NmrOneD 20560 Specdb::NmrOneD 20561 Specdb::MsMs 864 Specdb::MsMs 865 Specdb::MsMs 866 Specdb::MsMs 4260 Specdb::MsMs 4261 Specdb::MsMs 4262 Specdb::MsMs 4263 Specdb::MsMs 4264 Specdb::MsMs 4265 Specdb::MsMs 262518 Specdb::MsMs 262519 Specdb::MsMs 262520 Specdb::MsMs 282450 Specdb::MsMs 282451 Specdb::MsMs 282452 Specdb::MsMs 437419 Specdb::MsMs 437420 Specdb::MsMs 437421 Specdb::MsMs 437422 Specdb::MsMs 437423 Specdb::MsMs 439199 Specdb::MsMs 1473411 Specdb::MsMs 1473739 Specdb::MsMs 1473740 Specdb::MsMs 1473741 Specdb::NmrTwoD 1027 Specdb::NmrTwoD 1392 HMDB00634 874 553689 C02226 17626 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A Berg, Rudolph G. Catalytic preparation of citraconic and itaconic acids. U.S. (1972), 5 pp. http://hmdb.ca/system/metabolites/msds/000/000/553/original/HMDB00634.pdf?1358462166 3-isopropylmalate dehydratase large subunit P0A6A6 LEUC_ECOLI leuC http://ecmdb.ca/proteins/P0A6A6.xml 3-isopropylmalate dehydratase small subunit P30126 LEUD_ECOLI leuD http://ecmdb.ca/proteins/P30126.xml (R)-2-Methylmalate <> Citraconic acid + Water R03896 Citraconic acid + Water <> D-Erythro-3-Methylmalate R03898 Citraconic acid + Water > Citramalic acid PW_R003844 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 19.6 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 78400 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776