Showing Metabocard for trans-aconitate (BASm0000409)

Common Name	Trans-aconitate
Description	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
Molecular Formula	C₆H₆O₆
Average Mass	174.10820
Monoisotopic Mass	174.01644
IUPAC Name	(1E)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional Name	Trans-aconitic acid
CAS Registry Number	4023-65-8
SMILES	O=C([O-])/C=C(\CC(=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
CHEBI ID	CHEBI:15708
HMDB ID	HMDB0000958
State	Solid
Water Solubility	6.72e+00 g/l
logP	-0.41
logS	-1.41
pKa (Strongest Acidic)	3.15
pKa (Strongest Basic)	Not Available
Hydrogen Acceptor Count	6
Hydrogen Donor Count	3
Polar Surface Area	111.9 Å²
Rotatable Bond Count	4
Physiological Charge	-3
Formal Charge	0
Refractivity	35.23 m³·mol⁻¹
Polarizability	13.96

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