2.02012-08-03 14:57:54 -06002015-09-13 15:15:32 -0600ECMDB21397M2MDB001792Citraconic acidMesaconic 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 acidCitraconateMethylmaleateMethylmaleic acidC5H6O4130.0987130.02660868(2Z)-2-methylbut-2-enedioic acidcitraconic acid498-23-7C\C(=C\C(O)=O)C(O)=OInChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-HNEGQIOMVPPMNR-IHWYPQMZSA-NSolidCytoplasmlogp0.21logs-0.91solubility1.59e+01 g/lmelting_point88-94 oClogp0.35pka_strongest_acidic2.5iupac(2Z)-2-methylbut-2-enedioic acidaverage_mass130.0987mono_mass130.02660868smilesC\C(=C\C(O)=O)C(O)=OformulaC5H6O4inchiInChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-inchikeyHNEGQIOMVPPMNR-IHWYPQMZSA-Npolar_surface_area74.6refractivity28.96polarizability11.17rotatable_bond_count2acceptor_count4donor_count2physiological_charge-2formal_charge0Specdb::CMs1065Specdb::CMs8904Specdb::CMs29814Specdb::CMs31178Specdb::CMs31870Specdb::CMs37663Specdb::CMs159272Specdb::CMs1070803Specdb::CMs1070805Specdb::CMs1070806Specdb::CMs1070808Specdb::CMs1070810Specdb::NmrOneD1447Specdb::NmrOneD20542Specdb::NmrOneD20543Specdb::NmrOneD20544Specdb::NmrOneD20545Specdb::NmrOneD20546Specdb::NmrOneD20547Specdb::NmrOneD20548Specdb::NmrOneD20549Specdb::NmrOneD20550Specdb::NmrOneD20551Specdb::NmrOneD20552Specdb::NmrOneD20553Specdb::NmrOneD20554Specdb::NmrOneD20555Specdb::NmrOneD20556Specdb::NmrOneD20557Specdb::NmrOneD20558Specdb::NmrOneD20559Specdb::NmrOneD20560Specdb::NmrOneD20561Specdb::MsMs864Specdb::MsMs865Specdb::MsMs866Specdb::MsMs4260Specdb::MsMs4261Specdb::MsMs4262Specdb::MsMs4263Specdb::MsMs4264Specdb::MsMs4265Specdb::MsMs262518Specdb::MsMs262519Specdb::MsMs262520Specdb::MsMs282450Specdb::MsMs282451Specdb::MsMs282452Specdb::MsMs437419Specdb::MsMs437420Specdb::MsMs437421Specdb::MsMs437422Specdb::MsMs437423Specdb::MsMs439199Specdb::MsMs1473411Specdb::MsMs1473739Specdb::MsMs1473740Specdb::MsMs1473741Specdb::NmrTwoD1027Specdb::NmrTwoD1392HMDB00634874553689C0222617626Ishii, 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 316:593-597.17379776Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.ABerg, 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?13584621663-isopropylmalate dehydratase large subunitP0A6A6LEUC_ECOLIleuChttp://ecmdb.ca/proteins/P0A6A6.xml3-isopropylmalate dehydratase small subunitP30126LEUD_ECOLIleuDhttp://ecmdb.ca/proteins/P30126.xml(R)-2-Methylmalate <> Citraconic acid + WaterR03896Citraconic acid + Water <> D-Erythro-3-MethylmalateR03898Citraconic acid + Water > Citramalic acidPW_R00384448 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h19.6uM0.037 oCBW25113Stationary Phase, glucose limited784000Ishii, 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