1.0 2016-09-30 22:20:33 UTC 2020-05-11 20:52:29 UTC BMDB0000176 BMDB00176 Maleic acid Fumaric acid, also known as fumarate or E297, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Fumaric acid exists in all living species, ranging from bacteria to humans. Fumaric acid is a potentially toxic compound. (Z)-2-Butenedioic acid (Z)-Butenedioic acid cis-1,2-Ethylenedicarboxylic acid cis-But-2-enedioic acid cis-Butenedioic acid H2Male Toxilic acid Maleate (Z)-2-Butenedioate (Z)-Butenedioate cis-1,2-Ethylenedicarboxylate cis-But-2-enedioate cis-Butenedioate Toxilate (2Z)-2-Butenedioate (2Z)-2-Butenedioic acid (2Z)-But-2-enedioate (2Z)-But-2-enedioic acid (2Z)-Butene-2-dioate (2Z)-Butene-2-dioic acid 2-Butenedioate 2-Butenedioic acid cis-2-Butenedioate cis-2-Butenedioic acid Kyselina maleinova MAE Maleinic acid Malenic acid Malezid CM Scotchbond multipurpose etchant Maleic acid, disodium salt Maleic acid, monocopper (2+) salt Maleic acid, potassium salt Maleic acid, sodium salt Sodium maleate Hydrogen maleate Maleic acid, ammonium salt Maleic acid, calcium salt Maleic acid, iron salt Maleic acid, neodymium salt Maleic acid, dipotassium salt Maleic acid, monoammonium salt Maleic acid, monosodium salt C4H4O4 116.0722 116.010958616 (2Z)-but-2-enedioic acid maleic acid 110-16-7 OC(=O)\C=C/C(O)=O InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- VZCYOOQTPOCHFL-UPHRSURJSA-N belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Dicarboxylic acids and derivatives Dicarboxylic acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Organic oxides Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Unsaturated fatty acid Aliphatic acyclic compounds butenedioic acid Solid melting_point 130.5 °C water_solubility 441 mg/mL at 25 °C logp -0.48 SANGSTER (1994) logp 0.21 ALOGPS logs -0.68 ALOGPS logp -0.041 ChemAxon pka_strongest_acidic 3.05 ChemAxon iupac (2Z)-but-2-enedioic acid ChemAxon average_mass 116.0722 ChemAxon mono_mass 116.010958616 ChemAxon smiles OC(=O)\C=C/C(O)=O ChemAxon formula C4H4O4 ChemAxon inchi InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1- ChemAxon inchikey VZCYOOQTPOCHFL-UPHRSURJSA-N ChemAxon polar_surface_area 74.6 ChemAxon refractivity 24.61 ChemAxon polarizability 9.19 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 984 Specdb::NmrTwoD 1188 Specdb::CMs 415 Specdb::CMs 1036 Specdb::CMs 8094 Specdb::CMs 27693 Specdb::CMs 29705 Specdb::CMs 30138 Specdb::CMs 30617 Specdb::CMs 31050 Specdb::CMs 31936 Specdb::CMs 37339 Specdb::CMs 131405 Specdb::CMs 139139 Specdb::CMs 1052786 Specdb::CMs 1052788 Specdb::CMs 1052789 Specdb::NmrOneD 1144 Specdb::NmrOneD 142710 Specdb::NmrOneD 142711 Specdb::NmrOneD 142712 Specdb::NmrOneD 142713 Specdb::NmrOneD 142714 Specdb::NmrOneD 142715 Specdb::NmrOneD 142716 Specdb::NmrOneD 142717 Specdb::NmrOneD 142718 Specdb::NmrOneD 142719 Specdb::NmrOneD 142720 Specdb::NmrOneD 142721 Specdb::NmrOneD 142722 Specdb::NmrOneD 142723 Specdb::NmrOneD 142724 Specdb::NmrOneD 142725 Specdb::NmrOneD 142726 Specdb::NmrOneD 142727 Specdb::NmrOneD 142728 Specdb::NmrOneD 142729 Specdb::MsMs 280 Specdb::MsMs 281 Specdb::MsMs 282 Specdb::MsMs 3343 Specdb::MsMs 3344 Specdb::MsMs 3345 Specdb::MsMs 3346 Specdb::MsMs 3347 Specdb::MsMs 3348 Specdb::MsMs 3350 Specdb::MsMs 257739 Specdb::MsMs 257740 Specdb::MsMs 257741 Specdb::MsMs 277677 Specdb::MsMs 277678 Specdb::MsMs 277679 Specdb::MsMs 438089 Specdb::MsMs 438090 Specdb::MsMs 438091 Specdb::MsMs 438092 Specdb::MsMs 438093 Specdb::MsMs 439264 Specdb::MsMs 2252760 Specdb::MsMs 2254773 Specdb::MsMs 2255783 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pancreas Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Spleen Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C01384 DB04299 392248 444266 FDB008113 C00007417 18300 MALEATE Maleic_acid Dethloff, Christian; Barbarino, Sergio. Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride. Eur. Pat. Appl. (1998), 7 pp.