Record Information
Version1.0
Created at2020-04-17 18:37:33 UTC
Updated at2020-12-07 19:10:57 UTC
CannabisDB IDCDB004795
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namecis-Aconitic acid
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 is a moderately acidic compound (based on its pKa). cis-Aconitic acid exists in all living species, ranging from bacteria to humans. Within humans, cis-aconitic acid participates in a number of enzymatic reactions. In particular, cis-aconitic acid can be biosynthesized from citric acid through its interaction with the enzyme aconitate hydratase, mitochondrial. In addition, cis-aconitic acid can be converted into isocitric acid through the action of the enzyme aconitate hydratase, mitochondrial. In humans, cis-aconitic acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. cis-Aconitic acid is a bland tasting compound. Outside of the human body, cis-Aconitic acid is found, on average, in the highest concentration within milk (cow). cis-Aconitic acid has also been detected, but not quantified in, several different foods, such as japanese pumpkins, purple mangosteens, opium poppies, root vegetables, and shallots. This could make cis-aconitic acid a potential biomarker for the consumption of these foods. The cis-isomer of aconitic acid. cis-Aconitic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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-1-Propene-1,2,3-tricarboxylateGenerator
cis-AconitateGenerator
(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
Acid, citridicHMDB
Acid, citridinicHMDB
Aconitic acidHMDB
Acontic acidHMDB
Adonic acidHMDB
Achilleic acidHMDB
Acid, aconticHMDB
Acid, equiseticHMDB
Citridinic acidHMDB
Acid, achilleicHMDB
AconitateHMDB
Citridic acidHMDB
Pyrocitric acidHMDB
Acid, aconiticHMDB
Acid, adonicHMDB
Acid, carboxyglutaconicHMDB
Acid, pyrocitricHMDB
Carboxyglutaconic acidHMDB
Equisetic acidHMDB
Chemical FormulaC6H6O6
Average Molecular Weight174.11
Monoisotopic Molecular Weight174.0164
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 KeyGTZCVFVGUGFEME-IWQZZHSRSA-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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility400 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MScis-Aconitic acid, 3 TMS, GC-MS Spectrumsplash10-0002-1940000000-24c70788b42e3006de46Spectrum
GC-MScis-Aconitic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0940000000-3ab0a8161f2ec8f04452Spectrum
GC-MScis-Aconitic acid, 3 TMS, GC-MS Spectrumsplash10-00dj-9630000000-1dc322333cb48ef39588Spectrum
GC-MScis-Aconitic acid, 3 TMS, GC-MS Spectrumsplash10-004i-3591000000-a58ec1ba633b098e0867Spectrum
GC-MScis-Aconitic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1940000000-24c70788b42e3006de46Spectrum
GC-MScis-Aconitic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0940000000-3ab0a8161f2ec8f04452Spectrum
GC-MScis-Aconitic acid, non-derivatized, GC-MS Spectrumsplash10-00dj-9630000000-1dc322333cb48ef39588Spectrum
GC-MScis-Aconitic acid, non-derivatized, GC-MS Spectrumsplash10-004i-3591000000-a58ec1ba633b098e0867Spectrum
Predicted GC-MScis-Aconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06w9-4900000000-38239492ad0e66d6533bSpectrum
Predicted GC-MScis-Aconitic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9167000000-07ccdac5775cc3e75c95Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9300000000-1f04239a9a7133f89d08Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-49f5c2a7959cfbbbe09fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9100000000-d4857c30b96cf4786dbeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0911000000-3197b86ab2053b968bf9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-74977ead259f739d154bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-9f4cc240b2470f2bbb93Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-5034c256b831c6173452Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0912000000-a603cd799b70c1089dddSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-ce8dbec6a7b0d83b372cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-927f79de2cf5ffcb2c52Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-003r-0194000000-75d834c69fbfd0a2f7beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9200000000-e90e540bcd0659005472Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0edcc061c37b1fbb9fa1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000l-9000000000-1e762d38e4e5cabfcb6bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-9000000000-5602736cc28db9eb9085Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-c8ec5b3e604b870eab95Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9200000000-e90e540bcd0659005472Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-8e26562af9ae45eb3303Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-1900000000-7fec32a5e34c3b55d683Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w0-9600000000-ee172c3013370ab0da31Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-18635ce5a20ce1b78139Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2900000000-58bb75a2a1b28dbffd73Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-9300000000-19df730d01f07fcf6573Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aconitate hydratase, mitochondrialACO222q13.2Q99798 details
Cytoplasmic aconitate hydrataseACO19p21.1P21399 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytoplasmic aconitate hydrataseACO19p21.1P21399 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified5.28 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GabriolaDetected and Quantified1.48 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Island HoneyDetected and Quantified2.92 mg/g dry wt
    • Jiamin Zheng, Yil...
details
QuadraDetected and Quantified0.693 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi StarDetected and Quantified6.56 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified1.66 mg/g dry wt
    • Jiamin Zheng, Yil...
details
HMDB IDHMDB0000072
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008306
KNApSAcK IDC00001177
Chemspider ID558863
KEGG Compound IDC00417
BioCyc IDCIS-ACONITATE
BiGG IDNot Available
Wikipedia LinkCitric acid cycle
METLIN ID5130
PubChem Compound643757
PDB IDNot Available
ChEBI ID32805
References
General ReferencesNot Available

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
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