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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-10-17 22:24:14 UTC
HMDB IDHMDB00072
Secondary Accession Numbers
  • HMDB00461
Metabolite Identification
Common Namecis-Aconitic acid
Descriptioncis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle.
Structure
Thumb
Synonyms
ValueSource
(Z)-1-Propene-1,2,3-tricarboxylic acidChEBI
cis-1-Propene-1,2,3-tricarboxylic acidChEBI
(Z)-1-Propene-1,2,3-tricarboxylateGenerator
cis-AconitateGenerator
cis-1-Propene-1,2,3-tricarboxylateGenerator
(1Z)-1-Propene-1,2,3-tricarboxylateHMDB
(1Z)-1-Propene-1,2,3-tricarboxylic acidHMDB
(Z)-AconitateHMDB
(Z)-Aconitic acidHMDB
1-cis-2,3-PropenetricarboxylateHMDB
1-cis-2,3-Propenetricarboxylic acidHMDB
1-Propene-1,2,3-tricarboxylateHMDB
1-Propene-1,2,3-tricarboxylic acidHMDB
cis-AconateHMDB
cis-Aconic acidHMDB
cis-OxaloacetateHMDB
cis-Oxaloacetic acidHMDB
Chemical FormulaC6H6O6
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
IUPAC Name(1Z)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional Namecis-aconitic acid
CAS Registry Number585-84-2
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 KeyInChIKey=GTZCVFVGUGFEME-IWQZZHSRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glyoxylate and dicarboxylate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility400.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.72 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.23 m3·mol-1ChemAxon
Polarizability14.16 Å3ChemAxon
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0002-1940000000-24c70788b42e3006de46View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0940000000-3ab0a8161f2ec8f04452View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-9630000000-1dc322333cb48ef39588View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-3591000000-a58ec1ba633b098e0867View 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-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0911000000-3197b86ab2053b968bf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-74977ead259f739d154bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-9f4cc240b2470f2bbb93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-5034c256b831c6173452View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0912000000-a603cd799b70c1089dddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-ce8dbec6a7b0d83b372cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-927f79de2cf5ffcb2c52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-003r-0194000000-75d834c69fbfd0a2f7beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9200000000-e90e540bcd0659005472View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0edcc061c37b1fbb9fa1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000l-9000000000-1e762d38e4e5cabfcb6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-9000000000-5602736cc28db9eb9085View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-c8ec5b3e604b870eab95View 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
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
2-ketoglutarate dehydrogenase complex deficiencySMP00549Not Available
Citric Acid CycleSMP00057map00020
Congenital lactic acidosisSMP00546Not Available
Fumarase deficiencySMP00547Not Available
Glutaminolysis and CancerSMP02298Not Available
Mitochondrial complex II deficiencySMP00548Not Available
Pyruvate dehydrogenase deficiency (E2)SMP00551Not Available
Pyruvate dehydrogenase deficiency (E3)SMP00550Not Available
The oncogenic action of 2-hydroxyglutarateSMP02291Not Available
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria SMP02359Not Available
The oncogenic action of FumarateSMP02295Not Available
The oncogenic action of L-2-hydroxyglutarate in HydroxygluaricaciduriaSMP02358Not Available
The oncogenic action of SuccinateSMP02292Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified10.1 +/- 3.1 uMAdult (>18 years old)Female
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified2 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified20.0 (13.0-27.0) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified3.17 +/- 1.17 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.172 +/- 0.179 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.176 +/- 0.107 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.358 +/- 0.198 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.363 +/- 0.169 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified67.9 (14.3-100.7) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified73.8 (64.0-130.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified37.9 (17.3-63.3) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified29.8 (14.7-93.1) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified54.5 (32.4-76.6) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified48-103 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified20.9 (3.8-95.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified13 (2.7-44) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified35.95 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified<102.12 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified58-85 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified33.685 +/- 14.03 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.3(5.2-16.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified2.80 +/- 2.11 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified2.17 +/- 0.53 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified2.72 +/- 0.53 uMAdult (>18 years old)BothLewy body disease details
UrineDetected and Quantified38.74 +/- 40.952 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified32.0 (0.0-70.0) umol/mmol creatinineAdult (>18 years old)BothLung cancer details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [22024767 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [18953024 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008306
KNApSAcK IDC00001177
Chemspider ID558863
KEGG Compound IDC00417
BioCyc IDCIS-ACONITATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00072
Metagene LinkHMDB00072
METLIN ID5130
PubChem Compound643757
PDB IDNot Available
ChEBI ID32805
References
Synthesis ReferenceGutierrez, Eddie N.; Lamberti, Vincent. cis and trans Aconitic acids and their salts. U.S. (1978), 16 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [14708889 ]
  3. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  4. Swart PJ, Kuipers EM, Smit C, Van Der Strate BW, Harmsen MC, Meijer DK: Lactoferrin. Antiviral activity of lactoferrin. Adv Exp Med Biol. 1998;443:205-13. [9781360 ]
  5. Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. [813176 ]
  6. Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. [9693263 ]
  7. Swart PJ, Kuipers ME, Smit C, Pauwels R, deBethune MP, de Clercq E, Meijer DK, Huisman JG: Antiviral effects of milk proteins: acylation results in polyanionic compounds with potent activity against human immunodeficiency virus types 1 and 2 in vitro. AIDS Res Hum Retroviruses. 1996 Jun 10;12(9):769-75. [8738428 ]
  8. Matsuishi T, Urabe F, Percy AK, Komori H, Yamashita Y, Schultz RS, Ohtani Y, Kuriya N, Kato H: Abnormal carbohydrate metabolism in cerebrospinal fluid in Rett syndrome. J Child Neurol. 1994 Jan;9(1):26-30. [8151077 ]

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO2
Uniprot ID:
Q99798
Molecular weight:
85424.745
Reactions
Citric acid → cis-Aconitic acid + Waterdetails
Isocitric acid → cis-Aconitic acid + Waterdetails
General function:
Involved in metabolic process
Specific function:
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding. Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO1
Uniprot ID:
P21399
Molecular weight:
98398.14
Reactions
Citric acid → cis-Aconitic acid + Waterdetails
Isocitric acid → cis-Aconitic acid + Waterdetails