Record Information
Version2.0
Creation Date2012-05-31 13:02:31 -0600
Update Date2015-09-13 15:15:20 -0600
Secondary Accession Numbers
  • ECMDB00958
Identification
Name:trans-Aconitic acid
DescriptionTrans-aconitic acid is a member of the chemical class known as Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof). The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase. Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid. (WikiPedia)
Structure
Thumb
Synonyms:
  • (1E)-1-Propene-1,2,3-tricarboxylate
  • (1E)-1-propene-1,2,3-tricarboxylic acid
  • (1E)-Prop-1-ene-1,2,3-tricarboxylic
  • (1E)1-Propene-1,2,3-tricarboxylate
  • (1E)1-Propene-1,2,3-tricarboxylic acid
  • (E)-prop-1-ene-1,2,3-tricarboxylate
  • (e)-1-Propene-1,2,3-tricarboxylate
  • (E)-1-propene-1,2,3-tricarboxylic acid
  • (e)-Aconitate
  • (E)-Aconitic acid
  • (E)-prop-1-ene-1,2,3-tricarboxylate
  • (E)-prop-1-ene-1,2,3-tricarboxylic acid
  • 1-Propene-1-trans-2,3-tricarboxylate
  • 1-Propene-1-trans-2,3-tricarboxylic acid
  • 1-trans-Propene-1,2,3-tricarboxylate
  • 1-trans-Propene-1,2,3-tricarboxylic acid
  • trans-aconitic acid
  • Acid
  • TRA
  • trans-1-Propene-1,2,3-tricarboxylate
  • Trans-1-Propene-1,2,3-tricarboxylic acid
  • Trans-Aconitate
  • Trans-Aconitic acid
  • trans-Propene-1,2,3-tricarboxylate
  • Trans-Propene-1,2,3-tricarboxylic acid
Chemical Formula:C6H6O6
Weight:Average: 174.1082
Monoisotopic: 174.016437924
InChI Key:GTZCVFVGUGFEME-HNQUOIGGSA-N
InChI:InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+
CAS number:4023-65-8
IUPAC Name:(1E)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional IUPAC Name:trans aconitic acid
SMILES:OC(=O)C\C(=C/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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:187 - 191 °C
Experimental Properties:
PropertyValueSource
LogP:-0.728PhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.72 g/LALOGPS
logP-0.41ALOGPS
logP-0.52ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.23 m³·mol⁻¹ChemAxon
Polarizability13.96 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Secondary Metabolites: Glyoxylate cyclePW000967 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
96± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
72± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-003s-3971000000-d4adfdbddf5dc3badb47View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003s-3971000000-d4adfdbddf5dc3badb47View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1930000000-1043e640a069e4ed3c64View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06w9-4900000000-38239492ad0e66d6533bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9167000000-07ccdac5775cc3e75c95View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9300000000-1f04239a9a7133f89d08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-49f5c2a7959cfbbbe09fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9100000000-d4857c30b96cf4786dbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00b9-1900000000-51343d1269f884535ccaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9100000000-b3ebe9a6fedcb9608872View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-2d6b96d6e5ed92f0fdeeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000l-9000000000-d36114a1c7a0318b1f7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-f4ae4a72d5f2beed9106View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9200000000-49eaf4d6558839930e52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-1900000000-51343d1269f884535ccaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9100000000-b3ebe9a6fedcb9608872View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-4f60fbd245c1d58cd7d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000l-9000000000-d36114a1c7a0318b1f7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-f4ae4a72d5f2beed9106View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9200000000-49eaf4d6558839930e52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-a70cb799a63ff364ca21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000f-9000000000-eabb8ab38f98bb81b1eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9200000000-2d22108854c0dad1b598View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9300000000-3cf209c9f766f6c0efe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-8e26562af9ae45eb3303View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-1900000000-7fec32a5e34c3b55d683View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w0-9600000000-ee172c3013370ab0da31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-18635ce5a20ce1b78139View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2900000000-58bb75a2a1b28dbffd73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-9300000000-19df730d01f07fcf6573View in MoNA
MSMass Spectrum (Electron Ionization)splash10-000f-9100000000-814aded0eac117ddb550View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • 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
  • Koide K, Toyama J, Inoue N, Koshikawa S, Akizawa T, Takahashi K, Hidaka S, Yamane Y, Shinoda K, Nakao M, et al.: [Uremic peak 2a in high performance liquid chromatography--acidic components and their membrane permeability]. Nihon Jinzo Gakkai Shi. 1986 Nov;28(11):1481-9. Pubmed: 2950263
  • Tanaka K, Hine DG: Compilation of gas chromatographic retention indices of 163 metabolically important organic acids, and their use in detection of patients with organic acidurias. J Chromatogr. 1982 Apr 30;239:301-22. Pubmed: 7096501
  • Tsai MY, Oliphant C, Josephson MW: Identification of metabolites diagnostic for organic acidurias by simultaneous dual-column capillary gas chromatography. J Chromatogr. 1985 May 31;341(1):1-10. Pubmed: 4019674
  • 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:Gutierrez, Eddie N.; Lamberti, Vincent. Preparation of aconitic acid. U.S. (1978), 5 pp. CODEN: USXXAM US 4123459 19781031 CAN 90:103423 AN 1979:103423
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15708
HMDB IDHMDB00958
Pubchem Compound ID444212
Kegg IDC02341
ChemSpider ID392201
Wikipedia IDNot Available
BioCyc IDCPD-225
EcoCyc IDCPD-225
Ligand ExpoTRA

Enzymes

General function:
Involved in trans-aconitate 2-methyltransferase activity
Specific function:
Catalyzes the S-adenosylmethionine monomethyl esterification of trans-aconitate at high affinity and of cis- aconitate, isocitrate, and citrate at lower velocities and affinities
Gene Name:
tam
Uniprot ID:
P76145
Molecular weight:
29006
Reactions
S-adenosyl-L-methionine + trans-aconitate = S-adenosyl-L-homocysteine + (E)-3-(methoxycarbonyl)pent-2-enedioate.