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cis-aconitic acid (YMDB00630)

Identification
YMDB IDYMDB00630
Namecis-aconitic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptioncis-Aconitic acid, also known as cis-aconitate or acid, acontic, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. cis-Aconitic acid exists in all living species, ranging from bacteria to plants to humans. In yeast, cis-aconitic acid is involved in the metabolic pathway called the tca cycle pathway. Based on a literature review a significant number of articles have been published on cis-Aconitic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (1Z)-1-Propene-1,2,3-tricarboxylate
  • (1Z)-1-Propene-1,2,3-tricarboxylic acid
  • (Z)-1-Propene-1,2,3-tricarboxylate
  • (Z)-1-Propene-1,2,3-tricarboxylic acid
  • (Z)-Aconitate
  • (Z)-Aconitic acid
  • 1-cis-2,3-Propenetricarboxylate
  • 1-cis-2,3-Propenetricarboxylic acid
  • 1-propene-1,2,3-tricarboxylate
  • 1-propene-1,2,3-tricarboxylic acid
  • 1-Propene-1,2,3-tricarboxylic acid, (Z)-
  • 1-Propene-1,2,3-tricarboxylic acid, cis-
  • 1,cis-2, 3-Propenetricarboxylic acid
  • cis-1-Propene-1,2,3-tricarboxylate
  • cis-1-Propene-1,2,3-tricarboxylic acid
  • cis-Aconate
  • cis-Aconic acid
  • cis-Aconitate
  • cis-Aconitic acid
  • cis-Oxaloacetate
  • cis-Oxaloacetic acid
  • Acid, citridic
  • Acid, citridinic
  • Aconitic acid
  • Acontic acid
  • Adonic acid
  • Achilleic acid
  • Acid, acontic
  • Acid, equisetic
  • Citridinic acid
  • Acid, achilleic
  • Aconitate
  • Citridic acid
  • Pyrocitric acid
  • Acid, aconitic
  • Acid, adonic
  • Acid, carboxyglutaconic
  • Acid, pyrocitric
  • Carboxyglutaconic acid
  • Equisetic acid
CAS number585-84-2
WeightAverage: 174.1082
Monoisotopic: 174.016437924
InChI KeyGTZCVFVGUGFEME-IWQZZHSRSA-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(1Z)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional IUPAC Namecis-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 Solubility400 mg/mL at 25 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.72 g/LALOGPS
logP-0.41ALOGPS
logP-0.52ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.11ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.23 m³·mol⁻¹ChemAxon
Polarizability14.16 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
BlandFDB008306
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Glyoxylate cyclePW002419 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Citrate cycle (TCA cycle)ec00020 Map00020
Glyoxylate and dicarboxylate metabolismec00630 Map00630
SMPDB Reactions
Citric acid ↔ cis-aconitic acid + water
cis-aconitic acid + water ↔ Isocitric acid
Citric acid → water + cis-aconitic acid
cis-aconitic acid + water → D-threo-Isocitric acid
KEGG Reactions
cis-aconitic acid + water ↔ Isocitric acid
Citric acid ↔ cis-aconitic acid + water
cis-aconitic acid ↔ trans-Aconitic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0002-1940000000-24c70788b42e3006de46JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0940000000-3ab0a8161f2ec8f04452JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-9630000000-1dc322333cb48ef39588JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-3591000000-a58ec1ba633b098e0867JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1940000000-24c70788b42e3006de46JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0940000000-3ab0a8161f2ec8f04452JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-9630000000-1dc322333cb48ef39588JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-3591000000-a58ec1ba633b098e0867JSpectraViewer | 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableJSpectraViewer
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-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0911000000-3197b86ab2053b968bf9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-74977ead259f739d154bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-9f4cc240b2470f2bbb93JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-5034c256b831c6173452JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0912000000-a603cd799b70c1089dddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-ce8dbec6a7b0d83b372cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-927f79de2cf5ffcb2c52JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-003r-0194000000-75d834c69fbfd0a2f7beJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9200000000-e90e540bcd0659005472JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0edcc061c37b1fbb9fa1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000l-9000000000-1e762d38e4e5cabfcb6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-9000000000-5602736cc28db9eb9085JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-c8ec5b3e604b870eab95JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9200000000-e90e540bcd0659005472JSpectraViewer | 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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
  • Kanamasa, S., Dwiarti, L., Okabe, M., Park, E. Y. (2008). "Cloning and functional characterization of the cis-aconitic acid decarboxylase (CAD) gene from Aspergillus terreus." Appl Microbiol Biotechnol 80:223-229.18584171
Synthesis Reference:Gutierrez, Eddie N.; Lamberti, Vincent. cis and trans Aconitic acids and their salts. U.S. (1978), 16 pp.
External Links:
ResourceLink
CHEBI ID32805
HMDB IDHMDB00072
Pubchem Compound ID309
Kegg IDC00417
ChemSpider ID558863
FOODB IDFDB008306
WikipediaAconitic_acid
BioCyc IDCIS-ACONITATE

Enzymes

Protein Details
1. Aconitate hydratase, mitochondrial
General function:
Involved in metabolic process
Specific function:
Required for growth on nonfermentable carbon sources and for biosynthesis of glutamate
Gene Name:
ACO1
Uniprot ID:
P19414
Molecular weight:
85367.5
Reactions
Citrate → isocitrate.
Protein Details
2. Homoaconitase, mitochondrial
General function:
Involved in metabolic process
Specific function:
Responsible for the dehydration of cis-homoaconitate to homoisocitric acid
Gene Name:
LYS4
Uniprot ID:
P49367
Molecular weight:
75150.10156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate → (Z)-but-1-ene-1,2,4-tricarboxylate + H(2)O.