1.02011-09-21 00:06:43 UTC2019-11-26 03:21:00 UTCFDB0219972-Methylcitric acidMethylcitric 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-methylcitrate2-Hydroxy-1,2,3-butanetricarboxylate2-hydroxy-1,2,3-butanetricarboxylic acid2-hydroxybutane-1,2,3-tricarboxylate2-hydroxybutane-1,2,3-tricarboxylic acid2-methylcitrate2-methylcitric acidC7H10O7206.1501206.0426526742-hydroxy-1-methylpropane-1,2,3-tricarboxylic acidmethylcitric acid6061-96-7CC(C(O)=O)C(O)(CC(O)=O)C(O)=OInChI=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 derivativesOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesTricarboxylic acids and derivativesAliphatic acyclic compoundsAlpha hydroxy acids and derivativesCarbonyl compoundsCarboxylic acidsHydrocarbon derivativesOrganic oxidesTertiary alcoholsAlcoholAliphatic acyclic compoundAlpha-hydroxy acidCarbonyl groupCarboxylic acidHydrocarbon derivativeHydroxy acidOrganic oxideOrganic oxygen compoundOrganooxygen compoundTertiary alcoholTricarboxylic acid or derivativestricarboxylic acidSolidlogp-0.89logs-0.07solubility1.75e+02 g/llogp-0.78pka_strongest_acidic3.18pka_strongest_basic-4.3iupac2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acidaverage_mass206.1501mono_mass206.042652674smilesCC(C(O)=O)C(O)(CC(O)=O)C(O)=OformulaC7H10O7inchiInChI=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)inchikeyYNOXCRMFGMSKIJ-UHFFFAOYSA-Npolar_surface_area132.13refractivity40.2polarizability17.21rotatable_bond_count5acceptor_count7donor_count4physiological_charge-3formal_charge0Specdb::NmrOneD6682Specdb::NmrOneD6683Specdb::NmrOneD6684Specdb::NmrOneD6685Specdb::NmrOneD6686Specdb::NmrOneD6687Specdb::NmrOneD6688Specdb::NmrOneD6689Specdb::NmrOneD6690Specdb::NmrOneD6691Specdb::NmrOneD6692Specdb::NmrOneD6693Specdb::NmrOneD6694Specdb::NmrOneD6695Specdb::NmrOneD6696Specdb::NmrOneD6697Specdb::NmrOneD6698Specdb::NmrOneD6699Specdb::NmrOneD6700Specdb::NmrOneD6701Specdb::CMs19689Specdb::CMs37480Specdb::CMs168528Specdb::CMs1060058Specdb::CMs1060060Specdb::CMs1060062Specdb::CMs1060063Specdb::CMs1060064Specdb::CMs1060066Specdb::CMs1060068Specdb::CMs1060070Specdb::CMs1060072Specdb::CMs1060073Specdb::CMs1060075Specdb::CMs1060077Specdb::CMs1060079Specdb::CMs1060081Specdb::CMs1060083Specdb::CMs1060084Specdb::CMs1060086Specdb::CMs1060088Specdb::CMs1060090Specdb::CMs1060091Specdb::CMs1060093Specdb::CMs1060095Specdb::MsMs26378Specdb::MsMs26379Specdb::MsMs26380Specdb::MsMs32936Specdb::MsMs32937Specdb::MsMs32938Specdb::MsMs2283832Specdb::MsMs2283833Specdb::MsMs2283834Specdb::MsMs3081321Specdb::MsMs3081322Specdb::MsMs3081323HMDB0037930835#<Reference:0x0000555675d993f8>#<Reference:0x0000555675d99240>#<Reference:0x0000555675d99088>#<Reference:0x0000555675d98ed0>#<Reference:0x0000555675d98d18>#<Reference:0x0000555675d98b60>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Milk (Cow)Type 2specificMountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823