1.0 2011-09-21 00:06:43 UTC 2019-11-26 03:21:00 UTC FDB021997 2-Methylcitric acid Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270). MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine. (PMID: 17295121) [HMDB] (2S,3S)-2-methylcitrate 2-Hydroxy-1,2,3-butanetricarboxylate 2-hydroxy-1,2,3-butanetricarboxylic acid 2-hydroxybutane-1,2,3-tricarboxylate 2-hydroxybutane-1,2,3-tricarboxylic acid 2-methylcitrate 2-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. Tricarboxylic acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Tricarboxylic acids and derivatives Aliphatic acyclic compounds 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 tricarboxylic acid Solid logp -0.89 ALOGPS logs -0.07 ALOGPS solubility 1.75e+02 g/l 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 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 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 HMDB00379 30835 #<Reference:0x000055ce31dd1da0> #<Reference:0x000055ce31dd1be8> #<Reference:0x000055ce31dd1a30> #<Reference:0x000055ce31dd1878> #<Reference:0x000055ce31dd16c0> #<Reference:0x000055ce31dd1508> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823