ChemFOnt: Showing chemical card for trans-Aconitic acid (CFc000000765)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:15 UTC

Chemfont ID

CFc000000765

Molecule Identification

Common Name

trans-Aconitic acid

Definition

trans-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1E)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(e)-1-Propene-1,2,3-tricarboxylic acid	ChEBI
(1E)-1-Propene-1,2,3-tricarboxylate	Generator
(e)-1-Propene-1,2,3-tricarboxylate	Generator
trans-Aconitate	Generator
(1E)-Prop-1-ene-1,2,3-tricarboxylic	HMDB
(1E)1-Propene-1,2,3-tricarboxylate	HMDB
(1E)1-Propene-1,2,3-tricarboxylic acid	HMDB
(e)-Aconitic acid	HMDB
1-Propene-1-trans-2,3-tricarboxylic acid	HMDB
1-trans-Propene-1,2,3-tricarboxylic acid	HMDB
Acid	HMDB
TRA	HMDB
trans-1-Propene-1,2,3-tricarboxylic acid	HMDB
trans-Propene-1,2,3-tricarboxylic acid	HMDB
Acid, aconitic	HMDB
Acid, adonic	HMDB
Acid, carboxyglutaconic	HMDB
Acid, citridic	HMDB
Adonic acid	HMDB
Achilleic acid	HMDB
Acid, acontic	HMDB
Acid, pyrocitric	HMDB
Carboxyglutaconic acid	HMDB
Equisetic acid	HMDB
Pyrocitric acid	HMDB
Acid, achilleic	HMDB
Acid, equisetic	HMDB
Aconitate	HMDB
Citridic acid	HMDB
Citridinic acid	HMDB
Acid, citridinic	HMDB
Aconitic acid	HMDB
Acontic acid	HMDB

Chemical Formula

C₆H₆O₆

Average Molecular Weight

174.1082

Monoisotopic Molecular Weight

174.016437924

IUPAC Name

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

Traditional Name

trans aconitic acid

CAS Registry Number

4023-65-8

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 Key

GTZCVFVGUGFEME-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.

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:32806 )

Functional Ontology

Physiological effect

Health effect

Respiratory system disorder

Pulmonary disorder

Lung Cancer (HMDB: HMDB0000958)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000958)

Excreta

Biofluid or Excreta

Urine (PMID: 22157537)

Cellular substructure

Cytoplasm (HMDB: HMDB0000958)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000958)

Source

Endogenous

Endogenous (HMDB: HMDB0000958)

Plant

Exogenous

Food

Food (HMDB: HMDB0000958)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Soy

Soy bean (FooDB: FOOD00085)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Rice (FooDB: FOOD00125)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Secondary Metabolites: Glyoxylate Cycle (PathBank: SMP0121326)

Role

Biological role

Anti feedant (HMDB: HMDB0000958)

Industrial application

Agriculture

Pesticide (HMDB: HMDB0000958)

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000291)
Lung Cancer (MarkerDB: MDB00000291)
Amish Type Microcephaly (MarkerDB: MDB00000291)

Physical Properties

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)	3.15	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	13.96 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

External Links

HMDB ID

HMDB0000958

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

444212

PDB ID

Not Available

ChEBI ID

32806

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Gutierrez, Eddie N.; Lamberti, Vincent. Preparation of aconitic acid. U.S. (1978), 5 pp. CODEN: USXXAM US 4123459 19781031 CAN 90:103423 AN 1979:103423

Showing chemical card for trans-Aconitic acid (CFc000000765)

MOL for CFc000000765 (trans-Aconitic acid)

3D MOL for CFc000000765 (trans-Aconitic acid)

3D SDF for CFc000000765 (trans-Aconitic acid)

3D-SDF for CFc000000765 (trans-Aconitic acid)

PDB for CFc000000765 (trans-Aconitic acid)

3D PDB for CFc000000765 (trans-Aconitic acid)

SMILES for CFc000000765 (trans-Aconitic acid)

INCHI for CFc000000765 (trans-Aconitic acid)

Structure for CFc000000765 (trans-Aconitic acid)

3D Structure for CFc000000765 (trans-Aconitic acid)