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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:59:39 UTC
HMDB IDHMDB0000958
Secondary Accession Numbers
  • HMDB00958
Metabolite Identification
Common Nametrans-Aconitic acid
Descriptiontrans-Aconitic acid is normally present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase (EC 2.1.1.144) (PMID: 7096501 , 4019674 , 2950263 ). Trans-aconitate in the urine is a biomarker for the consumption of soy products.
Structure
Thumb
Synonyms
ValueSource
(1E)-1-Propene-1,2,3-tricarboxylic acidChEBI
(e)-1-Propene-1,2,3-tricarboxylic acidChEBI
(1E)-1-Propene-1,2,3-tricarboxylateGenerator
trans-AconitateGenerator
(e)-1-Propene-1,2,3-tricarboxylateGenerator
(1E)-Prop-1-ene-1,2,3-tricarboxylicHMDB
(1E)1-Propene-1,2,3-tricarboxylateHMDB
(1E)1-Propene-1,2,3-tricarboxylic acidHMDB
(e)-Aconitic acidHMDB
1-Propene-1-trans-2,3-tricarboxylic acidHMDB
1-trans-Propene-1,2,3-tricarboxylic acidHMDB
AcidHMDB
TRAHMDB
trans-1-Propene-1,2,3-tricarboxylic acidHMDB
trans-Propene-1,2,3-tricarboxylic acidHMDB
Acid, aconiticMeSH
Acid, adonicMeSH
Acid, carboxyglutaconicMeSH
Acid, citridicMeSH
Adonic acidMeSH
Achilleic acidMeSH
Acid, aconticMeSH
Acid, pyrocitricMeSH
Carboxyglutaconic acidMeSH
Equisetic acidMeSH
Pyrocitric acidMeSH
Acid, achilleicMeSH
Acid, equiseticMeSH
AconitateMeSH
Citridic acidMeSH
Citridinic acidMeSH
Acid, citridinicMeSH
Aconitic acidMeSH
Acontic acidMeSH
Chemical FormulaC6H6O6
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
IUPAC Name(1E)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional Nametrans-aconitic acid
CAS Registry Number4023-65-8
SMILES
OC(=O)C\C(=C/C(O)=O)C(O)=O
InChI Identifier
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+
InChI KeyGTZCVFVGUGFEME-HNQUOIGGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic 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
Ontology
Physiological effect

Health effect:

  Health condition:

    Cancer:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point187 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility472.5 mg/mLNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-003s-3971000000-d4adfdbddf5dc3badb47View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-MSsplash10-003s-3971000000-d4adfdbddf5dc3badb47View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-1930000000-1043e640a069e4ed3c64View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-000f-9100000000-814aded0eac117ddb550View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    UrineDetected and Quantified23.287 +/- 25.2 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified3.38 umol/mmol creatinineAdult (>18 years old)MaleNormal
      • Shaykhutdinov RA,...
    details
    UrineDetected and Quantified<102.12 umol/mmol creatinineChildren (1 - 18 years old)Both
    Normal
      • BC Children's Hos...
    details
    UrineDetected and Quantified11.506 +/- 16.612 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified6.6 (1.8-25.1) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified8.81 +/- 8.486 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified14.559 +/- 8.807 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Gastroesophageal reflux disease
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified4.5 +/- 4.5 umol/mmol creatinineNot SpecifiedBothLung cancer details
    UrineDetected and Quantified5.507 +/- 4.865 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    Associated Disorders and Diseases
    Disease References
    Lung Cancer
    1. Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB008305
    KNApSAcK IDNot Available
    Chemspider ID392201
    KEGG Compound IDC02341
    BioCyc IDCPD-225
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound444212
    PDB IDNot Available
    ChEBI ID32806
    References
    Synthesis ReferenceGutierrez, 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)
    General References
    1. 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 ]
    2. 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 ]
    3. 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 ]