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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:32:06 UTC
HMDB IDHMDB0000958
Secondary Accession Numbers
  • HMDB00958
Metabolite Identification
Common Nametrans-Aconitic acid
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 exists in all living species, ranging from bacteria to humans. trans-Aconitic acid is a dry, musty, and nut tasting compound. Outside of the human body, trans-aconitic acid has been detected, but not quantified in several different foods, such as garden tomato fruits, root vegetables, soy beans, and rices. trans-Aconitic acid is normally present in human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid in the urine is a biomarker for the consumption of soy products. trans-Aconitic acid is a substrate of enzyme trans-Aconitic acid 2-methyltransferase (EC2.1.1.144).
Structure
Data?1582752167
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
(e)-1-Propene-1,2,3-tricarboxylateGenerator
trans-AconitateGenerator
(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, aconiticHMDB
Acid, adonicHMDB
Acid, carboxyglutaconicHMDB
Acid, citridicHMDB
Adonic acidHMDB
Achilleic acidHMDB
Acid, aconticHMDB
Acid, pyrocitricHMDB
Carboxyglutaconic acidHMDB
Equisetic acidHMDB
Pyrocitric acidHMDB
Acid, achilleicHMDB
Acid, equiseticHMDB
AconitateHMDB
Citridic acidHMDB
Citridinic acidHMDB
Acid, citridinicHMDB
Aconitic acidHMDB
Acontic acidHMDB
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
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
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point187 - 191 °CNot Available
Boiling Point542.00 to 543.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility472.5 mg/mLNot Available
LogP-0.140The Good Scents Company Information System
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-Baker131.87530932474
DeepCCS[M+H]+Baker153.01830932474
AllCCS[M-H]-Not Available131.875http://allccs.zhulab.cn/database/detail?ID=AllCCS00001770
AllCCS[M+H]+Not Available153.018http://allccs.zhulab.cn/database/detail?ID=AllCCS00001770
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.72 g/LALOGPS
logP10(-0.41) g/LALOGPS
logP10(-0.52) g/LChemAxon
logS10(-1.4) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.67931661259
DarkChem[M-H]-133.06631661259
AllCCS[M+H]+137.8732859911
AllCCS[M-H]-129.60832859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - trans-Aconitic acid GC-MS (3 TMS)splash10-003s-3971000000-d4adfdbddf5dc3badb472014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Aconitic acid GC-MS (Non-derivatized)splash10-003s-3971000000-d4adfdbddf5dc3badb472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Aconitic acid GC-EI-TOF (Non-derivatized)splash10-0002-1930000000-1043e640a069e4ed3c642017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Aconitic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06w9-4900000000-38239492ad0e66d6533b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Aconitic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9167000000-07ccdac5775cc3e75c952017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Aconitic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000f-9100000000-814aded0eac117ddb5502015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-9300000000-1f04239a9a7133f89d082012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000f-9000000000-49f5c2a7959cfbbbe09f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000f-9100000000-d4857c30b96cf4786dbe2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-00b9-1900000000-51343d1269f884535cca2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-9100000000-b3ebe9a6fedcb96088722012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-9000000000-2d6b96d6e5ed92f0fdee2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-000l-9000000000-d36114a1c7a0318b1f7a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0006-9000000000-f4ae4a72d5f2beed91062012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-9200000000-49eaf4d6558839930e522012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOFsplash10-00b9-1900000000-51343d1269f884535cca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOFsplash10-000i-9100000000-b3ebe9a6fedcb96088722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-4f60fbd245c1d58cd7d52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOFsplash10-000l-9000000000-d36114a1c7a0318b1f7a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-f4ae4a72d5f2beed91062017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-9200000000-49eaf4d6558839930e522017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid 40V, Negative-QTOFsplash10-00di-9100000000-a70cb799a63ff364ca212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid 20V, Negative-QTOFsplash10-000f-9000000000-eabb8ab38f98bb81b1ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid 35V, Negative-QTOFsplash10-000i-9200000000-2d22108854c0dad1b5982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Aconitic acid 35V, Negative-QTOFsplash10-000i-9300000000-3cf209c9f766f6c0efe82021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Aconitic acid 10V, Positive-QTOFsplash10-004i-0900000000-8e26562af9ae45eb33032016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Aconitic acid 20V, Positive-QTOFsplash10-02di-1900000000-7fec32a5e34c3b55d6832016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Aconitic acid 40V, Positive-QTOFsplash10-01w0-9600000000-ee172c3013370ab0da312016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Aconitic acid 10V, Negative-QTOFsplash10-00fr-1900000000-18635ce5a20ce1b781392016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Aconitic acid 20V, Negative-QTOFsplash10-00b9-2900000000-58bb75a2a1b28dbffd732016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Aconitic acid 40V, Negative-QTOFsplash10-06rf-9300000000-19df730d01f07fcf65732016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified9.740-38.962 umol/mmol creatinineInfant (0-1 year 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified6.494-293.514 umol/mmol creatinineInfant (0-1 year old)Both
Amish lethal microcephaly
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 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Amish lethal microcephaly
  1. Kelley RI, Robinson D, Puffenberger EG, Strauss KA, Morton DH: Amish lethal microcephaly: a new metabolic disorder with severe congenital microcephaly and 2-ketoglutaric aciduria. Am J Med Genet. 2002 Nov 1;112(4):318-26. doi: 10.1002/ajmg.10529. [PubMed:12376931 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008305
KNApSAcK IDC00052231
Chemspider ID392201
KEGG Compound IDC02341
BioCyc IDCPD-225
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound444212
PDB IDNot Available
ChEBI ID32806
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000291
Good Scents IDrw1001681
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 ]