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Identification
YMDB IDYMDB00340
Nametrans-Aconitic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiontrans-Aconitic acid, also known as trans-aconitate or (e)-aconitic acid, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. trans-Aconitic acid is a weakly acidic compound (based on its pKa). trans-Aconitic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (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)-1-propene-1,2,3-tricarboxylic acid
  • (E)-Aconitic acid
  • 1-Propene-1-trans-2,3-tricarboxylic acid
  • 1-trans-Propene-1,2,3-tricarboxylic acid
  • ACONITATE ION
  • TRA
  • trans-1-Propene-1,2,3-tricarboxylic acid
  • trans-Aconitate
  • trans-Aconitic acid
  • trans-Propene-1,2,3-tricarboxylic acid
  • (1E)-1-Propene-1,2,3-tricarboxylate
  • (e)-1-Propene-1,2,3-tricarboxylate
  • Acid
  • Acid, aconitic
  • Acid, adonic
  • Acid, carboxyglutaconic
  • Acid, citridic
  • Adonic acid
  • Achilleic acid
  • Acid, acontic
  • Acid, pyrocitric
  • Carboxyglutaconic acid
  • Equisetic acid
  • Pyrocitric acid
  • Acid, achilleic
  • Acid, equisetic
  • Aconitate
  • Citridic acid
  • Citridinic acid
  • Acid, citridinic
  • Aconitic acid
  • Acontic acid
CAS number585-84-2
WeightAverage: 174.1082
Monoisotopic: 174.016437924
InChI KeyGTZCVFVGUGFEME-HNQUOIGGSA-N
InChIInChI=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+
IUPAC Name(1E)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional IUPAC Nametrans aconitic acid
Chemical FormulaC6H6O6
SMILESOC(=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
StateSolid
Charge0
Melting point125 °C
Experimental Properties
PropertyValueReference
Water Solubility472.5 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
DryFDB008305
MustyFDB008305
NutFDB008305
ToastedFDB008305
VegetableFDB008305
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
cis-aconitic acidtrans-Aconitic acid
trans-Aconitic acid + S-AdenosylmethionineS-Adenosylhomocysteine + (2E)-3-(methoxycarbonyl)pent-2-enedioic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-003s-3971000000-d4adfdbddf5dc3badb47JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003s-3971000000-d4adfdbddf5dc3badb47JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1930000000-1043e640a069e4ed3c64JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06w9-4900000000-38239492ad0e66d6533bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9167000000-07ccdac5775cc3e75c95JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9300000000-1f04239a9a7133f89d08JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-49f5c2a7959cfbbbe09fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9100000000-d4857c30b96cf4786dbeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00b9-1900000000-51343d1269f884535ccaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9100000000-b3ebe9a6fedcb9608872JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-2d6b96d6e5ed92f0fdeeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000l-9000000000-d36114a1c7a0318b1f7aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-f4ae4a72d5f2beed9106JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9200000000-49eaf4d6558839930e52JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-1900000000-51343d1269f884535ccaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9100000000-b3ebe9a6fedcb9608872JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-4f60fbd245c1d58cd7d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000l-9000000000-d36114a1c7a0318b1f7aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-f4ae4a72d5f2beed9106JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9200000000-49eaf4d6558839930e52JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-8e26562af9ae45eb3303JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-1900000000-7fec32a5e34c3b55d683JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w0-9600000000-ee172c3013370ab0da31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-18635ce5a20ce1b78139JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2900000000-58bb75a2a1b28dbffd73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-9300000000-19df730d01f07fcf6573JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000f-9100000000-814aded0eac117ddb550JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
  • Katz, J. E., Dumlao, D. S., Wasserman, J. I., Lansdown, M. G., Jung, M. E., Faull, K. F., Clarke, S. (2004). "3-Isopropylmalate is the major endogenous substrate of the Saccharomyces cerevisiae trans-aconitate methyltransferase." Biochemistry 43:5976-5986.15147181
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
External Links:
ResourceLink
CHEBI ID32805
HMDB IDHMDB00072
Pubchem Compound ID444212
Kegg IDC02341
ChemSpider ID392201
FOODB IDFDB008305
WikipediaAconitate
BioCyc IDCIS-ACONITATE

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the S-adenosylmethionine monomethyl esterification of trans-aconitate and 3-isopropylmalate at high affinity and of other molecules like cis-aconitate, isocitrate, and citrate at lower velocities and affinities. The function of trans-aconitate methylation appears to be in reducing the toxicity of this spontaneous breakdown product of cis-aconitate. The role of 3-isopropylmalate methylation is unclear but may represent a metabolic branch at 3-isopropylmalate, where some of the material is taken in the pathway leading to leucine and some is taken in a pathway to the 3-isopropylmalate methyl ester, a molecule that provides a signal to switch from vegetative to invasive growth in response to amino acid starvation
Gene Name:
TMT1
Uniprot ID:
P32643
Molecular weight:
34768.0
Reactions
S-adenosyl-L-methionine + trans-aconitate → S-adenosyl-L-homocysteine + (E)-2-(methoxycarbonylmethyl)butenedioate.