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Showing Compound cis-aconitate (FDB030729)

Record Information
Version1.0
Creation date2015-05-07 19:56:55 UTC
Update date2019-11-26 03:21:52 UTC
Primary IDFDB030729
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecis-aconitate
DescriptionCis-aconitic acid, also known as (Z)-1-propene-1,2,3-tricarboxylic acid or cis-aconitate, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Cis-aconitic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Cis-aconitic acid is a very mild, musty, and nutty tasting compound and can be found in a number of food items such as red beetroot, barley, corn, and oat, which makes cis-aconitic acid a potential biomarker for the consumption of these food products. Cis-aconitic acid can be found primarily in most biofluids, including urine, saliva, sweat, and breast milk, as well as in human prostate tissue. Cis-aconitic acid exists in all living species, ranging from bacteria to humans. In humans, cis-aconitic acid is involved in several metabolic pathways, some of which include the oncogenic action of succinate, congenital lactic acidosis, the oncogenic action of fumarate, and the oncogenic action of 2-hydroxyglutarate. Cis-aconitic acid is also involved in several metabolic disorders, some of which include pyruvate dehydrogenase deficiency (E3), glutaminolysis and cancer, mitochondrial complex II deficiency, and the oncogenic action of d-2-hydroxyglutarate in hydroxygluaricaciduria. Moreover, cis-aconitic acid is found to be associated with schizophrenia and lung Cancer.
CAS Number585-84-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O6
IUPAC name(1Z)-prop-1-ene-1,2,3-tricarboxylic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)C\C(=C\C(O)=O)C(O)=O
Average Molecular Weight174.1082
Monoisotopic Molecular Weight174.016437924
Classification
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAconitic acid, 3 TMS, GC-MS Spectrumsplash10-0002-1940000000-24c70788b42e3006de46Spectrum
GC-MSAconitic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0940000000-3ab0a8161f2ec8f04452Spectrum
GC-MSAconitic acid, 3 TMS, GC-MS Spectrumsplash10-00dj-9630000000-1dc322333cb48ef39588Spectrum
GC-MSAconitic acid, 3 TMS, GC-MS Spectrumsplash10-004i-3591000000-a58ec1ba633b098e0867Spectrum
GC-MSAconitic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1940000000-24c70788b42e3006de46Spectrum
GC-MSAconitic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0940000000-3ab0a8161f2ec8f04452Spectrum
GC-MSAconitic acid, non-derivatized, GC-MS Spectrumsplash10-00dj-9630000000-1dc322333cb48ef39588Spectrum
GC-MSAconitic acid, non-derivatized, GC-MS Spectrumsplash10-004i-3591000000-a58ec1ba633b098e0867Spectrum
Predicted GC-MSAconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06w9-4900000000-38239492ad0e66d6533bSpectrum
Predicted GC-MSAconitic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9167000000-07ccdac5775cc3e75c95Spectrum
Predicted GC-MSAconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAconitic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9300000000-1f04239a9a7133f89d082012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-49f5c2a7959cfbbbe09f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000f-9100000000-d4857c30b96cf4786dbe2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0911000000-3197b86ab2053b968bf92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-74977ead259f739d154b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-9f4cc240b2470f2bbb932012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-5034c256b831c61734522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0912000000-a603cd799b70c1089ddd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-9000000000-ce8dbec6a7b0d83b372c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-927f79de2cf5ffcb2c522012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-003r-0194000000-75d834c69fbfd0a2f7be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9200000000-e90e540bcd06590054722012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-0edcc061c37b1fbb9fa12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000l-9000000000-1e762d38e4e5cabfcb6b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-000f-9000000000-5602736cc28db9eb90852012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9400000000-c8ec5b3e604b870eab952012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00fr-0900000000-aad30bb884e0e9a5f01c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9200000000-e90e540bcd06590054722017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-8e26562af9ae45eb33032016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02di-1900000000-7fec32a5e34c3b55d6832016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w0-9600000000-ee172c3013370ab0da312016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-18635ce5a20ce1b781392016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-2900000000-58bb75a2a1b28dbffd732016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rf-9300000000-19df730d01f07fcf65732016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference