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Record Information
Version	2.0
Creation Date	2012-05-31 14:08:34 -0600
Update Date	2015-06-03 15:54:52 -0600
Secondary Accession Numbers	ECMDB06471
Identification
Name:	Methylisocitric acid
Description	Methylisocitric acid is a product of bacterial metabolism in the gut. It can be produced by 2-methylisocitrate lyase and by 2-methylisocitrate dehydratase.
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xac7d9b6c> Close
Synonyms:	(2R,3S)2-methylisocitrate (2R,3S)2-methylisocitric acid (2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylate (2S,3R)-3-Hydroxybutane-1,2,3-tricarboxylic acid 3-Carboxy-2,3-dideoxy-4-C-methylpentarate 3-Carboxy-2,3-dideoxy-4-C-methylpentaric acid 3-Hydroxy-1,2,3-butanetricarboxylate 3-Hydroxy-1,2,3-butanetricarboxylic acid 3-Hydroxybutane-1,2,3-tricarboxylate 3-Hydroxybutane-1,2,3-tricarboxylic acid threo-Ds-2-methylisocitrate a-Methylisocitrate a-Methylisocitric acid Alpha-Methylisocitrate Alpha-Methylisocitric acid D.L-Methylisocitrate D.L-Methylisocitric acid DL-Methylisocitrate DL-Methylisocitric acid DL-threo-a-Methylisocitrate DL-threo-a-Methylisocitric acid DL-threo-alpha-methylisocitrate DL-threo-alpha-methylisocitric acid DL-threo-α-Methylisocitrate DL-threo-α-Methylisocitric acid Methylisocitrate Methylisocitric acid threo-a-Methylisocitrate threo-a-Methylisocitric acid Threo-alpha-methylisocitrate Threo-alpha-methylisocitric acid Threo-Ds-2-methylisocitrate Threo-Ds-2-methylisocitric acid threo-α-Methylisocitrate threo-α-Methylisocitric acid α-Methylisocitrate α-Methylisocitric acid
Chemical Formula:	C7H10O7
Weight:	Average: 206.1501 Monoisotopic: 206.042652674
InChI Key:	HHKPKXCSHMJWCF-UHFFFAOYSA-N
InChI:	InChI=1S/C7H10O7/c1-7(14,6(12)13)3(5(10)11)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)
CAS number:	Not Available
IUPAC Name:	1-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid
Traditional IUPAC Name:	α-methylisocitric acid
SMILES:	CC(O)(C(CC(O)=O)C(O)=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Tricarboxylic acids and derivatives
Direct Parent	Tricarboxylic acids and derivatives
Alternative Parents	Alpha hydroxy acids and derivatives Tertiary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Tricarboxylic acid or derivatives Hydroxy acid Alpha-hydroxy acid Tertiary alcohol Carboxylic acid Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Alcohol Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 149 g/L ALOGPS logP -0.87 ALOGPS logP -1 ChemAxon logS -0.14 ALOGPS pKa (Strongest Acidic) 3.17 ChemAxon pKa (Strongest Basic) -4.1 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 132.13 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 40.43 m³·mol⁻¹ ChemAxon Polarizability 17.37 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Cis-2-Methylaconitate + Water <> Methylisocitric acid Methylisocitric acid <> Pyruvic acid + Succinic acid Methylisocitric acid <> Cis-2-Methylaconitate + Water Methylisocitric acid > Succinic acid + Pyruvic acid Cis-2-Methylaconitate > Water + Methylisocitric acid Methylisocitric acid <> Pyruvic acid + Succinic acid Methylisocitric acid <> Pyruvic acid + Succinic acid
SMPDB Pathways:	Propanoate metabolism PW000940
KEGG Pathways:	Propanoate metabolism ec00640
EcoCyc Pathways:	2-methylcitrate cycle I PWY0-42
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000i-9700000000-5e955ef633a08113ea4b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-004i-6237900000-699512d84d6d00556b85 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000l-0900000000-f2ba7990914621684f43 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00xs-6900000000-56bcf049292c1d2aec9f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-01bc-5900000000-5450b7d1dc2e0d752d8f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0909-2910000000-76e456521d06eb2df306 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014i-2900000000-9ff275785270b3b9744a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00di-9300000000-08a246451feb097e60ee View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-0900000000-1f979af8cdefad8b7fc2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014i-0900000000-72ddc9d43332ef4d4c1e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014l-7900000000-b552ff6cfa53a6d1478c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000j-0910000000-69d3ffec30c69b150998 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fxy-2900000000-cfe61511f4feda222931 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00di-9100000000-7f3760d40cf2db6bf9eb View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15607 HMDB ID HMDB06471 Pubchem Compound ID 513 Kegg ID C04593 ChemSpider ID 498 Wikipedia ID Not Available BioCyc ID CPD-618 EcoCyc ID CPD-618

Enzymes