1.0 2016-09-30 22:34:01 UTC 2020-05-05 18:39:50 UTC BMDB0000634 BMDB00634 Citraconic acid Citraconic acid, also known as 2-methylmaleate or methylmaleic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Citraconic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Citraconic acid exists in all living organisms, ranging from bacteria to humans. (Z)-2-Methyl-2-butenedioic acid 2-Methyl-2-butenedioic acid 2-Methylmaleic acid alpha-Methylmaleic acid cis-2-Methylbutenedioic acid cis-Methylbutenedioic acid Citraconsaeure Methyl-maleinsaeure Methylmaleic acid Citraconate (Z)-2-Methyl-2-butenedioate 2-Methyl-2-butenedioate 2-Methylmaleate a-Methylmaleate a-Methylmaleic acid alpha-Methylmaleate Α-methylmaleate Α-methylmaleic acid cis-2-Methylbutenedioate cis-Methylbutenedioate Methylmaleate Citraconic acid, ammonium salt Citraconic acid, calcium salt Citraconic acid, sodium salt Methylfumaric acid (e)-2-Methyl-2-butenedioic acid Citraconic acid, (e)-isomer Mesaconic acid Monomethylfumarate 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 belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Methyl-branched fatty acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Dicarboxylic acid or derivatives Hydrocarbon derivative Methyl-branched fatty acid Organic oxide Organic oxygen compound Organooxygen compound Unsaturated fatty acid Aliphatic acyclic compounds Dicarboxylic acids dicarboxylic acid Solid melting_point 88 - 94 °C water_solubility 783.0 mg/mL logp 0.21 ALOGPS logs -0.91 ALOGPS 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 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::MsIr 691 Specdb::MsIr 692 Specdb::MsIr 693 Specdb::NmrTwoD 1027 Specdb::NmrTwoD 1392 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::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::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 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 Milk Raw milk, by GC-TOF/MS Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Milk Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was identified by probable match parameters of the NIST Mass Spectral Search Program Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 C02226 FDB022155 553689 DB04734 643798 C00052049 17626 2-METHYLMALEATE Citraconic_acid 5607 Berg, Rudolph G. Catalytic preparation of citraconic and itaconic acids. U.S. (1972), 5 pp. Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412