Showing Compound Aconitic acid (FDB008304)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:01 UTC

Update date

2025-11-18 23:09:03 UTC

Primary ID

FDB008304

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Aconitic acid

Description

cis-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.

CAS Number

499-12-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(Z)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
cis-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(Z)-1-Propene-1,2,3-tricarboxylate	Generator
cis-1-Propene-1,2,3-tricarboxylate	Generator
cis-Aconitate	Generator
(1Z)-1-Propene-1,2,3-tricarboxylate	HMDB
(1Z)-1-Propene-1,2,3-tricarboxylic acid	HMDB
(Z)-Aconitate	HMDB
(Z)-Aconitic acid	HMDB
1-cis-2,3-Propenetricarboxylate	HMDB
1-cis-2,3-Propenetricarboxylic acid	HMDB
1-Propene-1,2,3-tricarboxylate	HMDB
1-Propene-1,2,3-tricarboxylic acid	HMDB
cis-Aconate	HMDB
cis-Aconic acid	HMDB
cis-Oxaloacetate	HMDB
cis-Oxaloacetic acid	HMDB
Acid, citridic	HMDB
Acid, citridinic	HMDB
Aconitic acid	HMDB
Acontic acid	HMDB
Adonic acid	HMDB
Achilleic acid	HMDB
Acid, acontic	HMDB
Acid, equisetic	HMDB
Citridinic acid	HMDB
Acid, achilleic	HMDB
Aconitate	HMDB
Citridic acid	HMDB
Pyrocitric acid	HMDB
Acid, aconitic	HMDB
Acid, adonic	HMDB
Acid, carboxyglutaconic	HMDB
Acid, pyrocitric	HMDB
Carboxyglutaconic acid	HMDB
Equisetic acid	HMDB
1-Propene-1,2,3-tricarboxylic acid, 9CI	db_source
1,2,3-Propenetricarboxylic acid	biospider
3-Carboxy-2-pentenedioic acid	db_source
3-Carboxyglutaconic acid	biospider
Achilleaic acid	db_source
FEMA 2010	db_source
Propene-1,2,3-tricarboxylic acid	biospider

Predicted Properties

Property	Value	Source
Water Solubility	6.72 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	-0.52	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.11	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	35.23 m³·mol⁻¹	ChemAxon
Polarizability	14.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H6O6

IUPAC name

(1Z)-prop-1-ene-1,2,3-tricarboxylic acid

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 Key

GTZCVFVGUGFEME-IWQZZHSRSA-N

Isomeric SMILES

OC(=O)C\C(=C\C(O)=O)C(O)=O

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

Classification

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

aconitic acid (CHEBI:32805 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Cancer:

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Prostate

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 41.39%; H 3.47%; O 55.14%	DFC
Melting Point	198-199°C (decomp)
Boiling Point	Not Available
Experimental Water Solubility	333 mg/mL at 15 oC	BEILSTEIN
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Aconitic acid, 3 TMS, GC-MS Spectrum	splash10-0002-1940000000-24c70788b42e3006de46	Spectrum
GC-MS	Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0940000000-3ab0a8161f2ec8f04452	Spectrum
GC-MS	Aconitic acid, 3 TMS, GC-MS Spectrum	splash10-00dj-9630000000-1dc322333cb48ef39588	Spectrum
GC-MS	Aconitic acid, 3 TMS, GC-MS Spectrum	splash10-004i-3591000000-a58ec1ba633b098e0867	Spectrum
GC-MS	Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-0002-1940000000-24c70788b42e3006de46	Spectrum
GC-MS	Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-0002-0940000000-3ab0a8161f2ec8f04452	Spectrum
GC-MS	Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-00dj-9630000000-1dc322333cb48ef39588	Spectrum
GC-MS	Aconitic acid, non-derivatized, GC-MS Spectrum	splash10-004i-3591000000-a58ec1ba633b098e0867	Spectrum
Predicted GC-MS	Aconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06w9-4900000000-38239492ad0e66d6533b	Spectrum
Predicted GC-MS	Aconitic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9167000000-07ccdac5775cc3e75c95	Spectrum
Predicted GC-MS	Aconitic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Aconitic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9300000000-1f04239a9a7133f89d08	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9000000000-49f5c2a7959cfbbbe09f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000f-9100000000-d4857c30b96cf4786dbe	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0911000000-3197b86ab2053b968bf9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-9000000000-74977ead259f739d154b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-9f4cc240b2470f2bbb93	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-5034c256b831c6173452	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0912000000-a603cd799b70c1089ddd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-9000000000-ce8dbec6a7b0d83b372c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-927f79de2cf5ffcb2c52	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-003r-0194000000-75d834c69fbfd0a2f7be	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00fr-0900000000-aad30bb884e0e9a5f01c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9200000000-e90e540bcd0659005472	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-0edcc061c37b1fbb9fa1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-000l-9000000000-1e762d38e4e5cabfcb6b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-000f-9000000000-5602736cc28db9eb9085	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9400000000-c8ec5b3e604b870eab95	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00fr-0900000000-aad30bb884e0e9a5f01c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9200000000-e90e540bcd0659005472	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-8e26562af9ae45eb3303	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02di-1900000000-7fec32a5e34c3b55d683	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01w0-9600000000-ee172c3013370ab0da31	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-1900000000-18635ce5a20ce1b78139	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-2900000000-58bb75a2a1b28dbffd73	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rf-9300000000-19df730d01f07fcf6573	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

22211

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB0000072

CRC / DFC (Dictionary of Food Compounds) ID

DFV04-S:DFV04-S

EAFUS ID

Dr. Duke ID

ACONITIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001177

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1108671

SuperScent ID

Not Available

Wikipedia ID

Aconitic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
very mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.