1.0 2016-09-30 22:29:38 UTC 2020-05-11 20:36:55 UTC BMDB0000379 BMDB00379 2-Methylcitric acid 2-Methylcitric acid, also known as 2-methylcitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Methylcitric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methylcitric acid exists in all living organisms, ranging from bacteria to humans. 2-Methylcitric acid is a potentially toxic compound. 2-Methylcitric acid has been found to be associated with several diseases known as iron deficiency and crohn's disease; also 2-methylcitric acid has been linked to several inborn metabolic disorders including vitamin B12 deficiency, isovaleric acidemia, and propionic acidemia. 2-Hydroxy-1,2,3-butanetricarboxylic acid 2-Hydroxy-1,2,3-butanetricarboxylate 2-Methylcitrate (2S,3S)-2-Methylcitrate 2-Hydroxybutane-1,2,3-tricarboxylate 2-Hydroxybutane-1,2,3-tricarboxylic acid 2-Methylcitric acid, 3H-labeled 3-Carboxy-3-hydroxy-2-methylpentanedioic acid Methylcitric acid C7H10O7 206.1501 206.042652674 2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid methylcitric acid 6061-96-7 CC(C(O)=O)C(O)(CC(O)=O)C(O)=O InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13) YNOXCRMFGMSKIJ-UHFFFAOYSA-N belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Tricarboxylic acids and derivatives Tricarboxylic acids and derivatives Alpha hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Organic oxides Tertiary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Carbonyl group Carboxylic acid Hydrocarbon derivative Hydroxy acid Organic oxide Organic oxygen compound Organooxygen compound Tertiary alcohol Tricarboxylic acid or derivatives Aliphatic acyclic compounds tricarboxylic acid Solid logp -0.89 ALOGPS logs -0.07 ALOGPS logp -0.78 ChemAxon pka_strongest_acidic 3.18 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid ChemAxon average_mass 206.1501 ChemAxon mono_mass 206.042652674 ChemAxon smiles CC(C(O)=O)C(O)(CC(O)=O)C(O)=O ChemAxon formula C7H10O7 ChemAxon inchi InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13) ChemAxon inchikey YNOXCRMFGMSKIJ-UHFFFAOYSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 40.2 ChemAxon polarizability 17.21 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -3 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::MsMs 26378 Specdb::MsMs 26379 Specdb::MsMs 26380 Specdb::MsMs 32936 Specdb::MsMs 32937 Specdb::MsMs 32938 Specdb::MsMs 2283832 Specdb::MsMs 2283833 Specdb::MsMs 2283834 Specdb::MsMs 3081321 Specdb::MsMs 3081322 Specdb::MsMs 3081323 Specdb::NmrOneD 6682 Specdb::NmrOneD 6683 Specdb::NmrOneD 6684 Specdb::NmrOneD 6685 Specdb::NmrOneD 6686 Specdb::NmrOneD 6687 Specdb::NmrOneD 6688 Specdb::NmrOneD 6689 Specdb::NmrOneD 6690 Specdb::NmrOneD 6691 Specdb::NmrOneD 6692 Specdb::NmrOneD 6693 Specdb::NmrOneD 6694 Specdb::NmrOneD 6695 Specdb::NmrOneD 6696 Specdb::NmrOneD 6697 Specdb::NmrOneD 6698 Specdb::NmrOneD 6699 Specdb::NmrOneD 6700 Specdb::NmrOneD 6701 Specdb::CMs 19689 Specdb::CMs 37480 Specdb::CMs 168528 Specdb::CMs 1060058 Specdb::CMs 1060060 Specdb::CMs 1060062 Specdb::CMs 1060063 Specdb::CMs 1060064 Specdb::CMs 1060066 Specdb::CMs 1060068 Specdb::CMs 1060070 Specdb::CMs 1060072 Specdb::CMs 1060073 Specdb::CMs 1060075 Specdb::CMs 1060077 Specdb::CMs 1060079 Specdb::CMs 1060081 Specdb::CMs 1060083 Specdb::CMs 1060084 Specdb::CMs 1060086 Specdb::CMs 1060088 Specdb::CMs 1060090 Specdb::CMs 1060091 Specdb::CMs 1060093 Specdb::CMs 1060095 Milk Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Placenta 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 FDB021997 500 515 30835 39369 5368 Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander. Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain. PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007101866 A2 20070913 CAN 147:363646 AN 2007:1033111 Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684