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Record Information
Version	2.0
Creation Date	2012-05-31 14:08:14 -0600
Update Date	2015-06-03 15:54:51 -0600
Secondary Accession Numbers	ECMDB06357
Identification
Name:	Cis-2-Methylaconitate
Description	cis-2-Methylaconitate is produced due to the dehydration of 2-methylcitrate in 2-methylcitric acid cycle. The cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. (PMID: 17567742)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb00f4604> Close
Synonyms:	(2Z)-but-2-ene-1,2,3-tricarboxylate (2Z)-but-2-ene-1,2,3-tricarboxylic acid (Z)-2-Butene-1,2,3-tricarboxylate (Z)-2-Butene-1,2,3-tricarboxylic acid (Z)-But-2-ene-1,2,3-tricarboxylate (Z)-But-2-ene-1,2,3-tricarboxylic acid 2-methyl-cis-aconitate 2-Methyl-cis-aconitate 2-Methyl-cis-aconitic acid 2-methylaconitate 2-Methylaconitic acid a-Methyl-cis-aconitate a-Methyl-cis-aconitic acid a-Methylaconitate a-Methylaconitic acid Alpha-Methyl-cis-aconitate Alpha-Methyl-cis-aconitic acid Alpha-Methylaconitate Alpha-Methylaconitic acid Cis-2-Butene-1,2,3-tricarboxylate Cis-2-Butene-1,2,3-tricarboxylic acid Cis-2-Methylaconitic acid α-Methyl-cis-aconitate α-Methyl-cis-aconitic acid α-Methylaconitate α-Methylaconitic acid
Chemical Formula:	C7H8O6
Weight:	Average: 188.1348 Monoisotopic: 188.032087988
InChI Key:	NUZLRKBHOBPTQV-ARJAWSKDSA-N
InChI:	InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-
CAS number:	6061-93-4
IUPAC Name:	(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional IUPAC Name:	α-methylaconitate
SMILES:	C\C(C(O)=O)=C(/CC(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	Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Tricarboxylic acid or derivatives Carboxylic acid Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	tricarboxylic acid (CHEBI:16717 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.16 g/L ALOGPS logP -0.33 ALOGPS logP -0.13 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 2.25 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 111.9 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 39.59 m³·mol⁻¹ ChemAxon Polarizability 15.55 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 Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water Methylcitric acid <> Cis-2-Methylaconitate + Water Methylisocitric acid <> Cis-2-Methylaconitate + Water Methylcitric acid > Water + Cis-2-Methylaconitate (2S,3R)-3-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate > Cis-2-Methylaconitate + Water 2-Methylcitric acid + Methylcitric acid > Water + Cis-2-Methylaconitate Cis-2-Methylaconitate > Water + Methylisocitric acid Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water Methylcitric acid + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate <> Cis-2-Methylaconitate + Water
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 splash10-002g-6900000000-ffb445dd87ee618648ff View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-0079-9388000000-0ff4121be9b872f0c1ab 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 splash10-00di-1900000000-202d4666a34f5b4f09f9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00fs-5900000000-9c256387d352a7a6ebb2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-002b-9500000000-027a2750edf1831b7088 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000f-1900000000-e925a682247370a2fa7f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00mn-4900000000-ec6a931ab7e2e1653ea8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00dj-9200000000-07d3197108036a4cb0ff View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002e-4900000000-fe6584e3d383728ee001 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0002-9200000000-80caf61386c108fcd0b4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0002-9100000000-327d1a78edc99f8fe760 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0fi0-0900000000-734e75ff99c6e837cdcb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-002b-9600000000-065cce37ffa797ab854c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-006t-9000000000-925f178b16f34b5de908 View in MoNA 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 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Garvey, G. S., Rocco, C. J., Escalante-Semerena, J. C., Rayment, I. (2007). "The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function." Protein Sci 16:1274-1284. Pubmed: 17567742 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
Synthesis Reference:	Tabuchi, Takeshi; Uchiyama, Hiroo. Methylcitrate condensing and methylisocitrate cleaving enzymes. Evidence for the pathway of oxidation of propionyl-CoA to pyruvate via C7-tricarboxylic acids. Agricultural and Biological Chemistry (1975), 39(10),
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16717 HMDB ID HMDB06357 Pubchem Compound ID 3080625 Kegg ID C04225 ChemSpider ID 2338376 Wikipedia ID Not Available BioCyc ID CPD-1136 EcoCyc ID CPD-1136

Enzymes