Showing Metabocard for cis-aconitate (BASm0000607)

Common NameCis-aconitate
Descriptioncis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle.
Structure
Molecular FormulaC6H6O6
Average Mass174.10820
Monoisotopic Mass174.01644
IUPAC Name(1Z)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional NameCis-aconitic acid
CAS Registry Number585-84-2
SMILESO=C([O-])/C=C(/CC(=O)[O-])C(=O)[O-]
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
CHEBI IDCHEBI:16383
HMDB IDHMDB0000072
Pathways
NameSMPDB/PathBank
Citric Acid Cycle
Congenital lactic acidosis
Fumarase deficiency
Mitochondrial complex II deficiency
2-ketoglutarate dehydrogenase complex deficiency
Pyruvate dehydrogenase deficiency (E3)
Pyruvate dehydrogenase deficiency (E2)
The oncogenic action of 2-hydroxyglutarate
The Oncogenic Action of Succinate
The Oncogenic Action of Fumarate
Glutaminolysis and Cancer
The oncogenic action of L-2-hydroxyglutarate in Hydroxygluaricaciduria
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria
StateSolid
Water Solubility6.72e+00 g/l
logP-0.41
logS-1.41
pKa (Strongest Acidic)2.11
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count6
Hydrogen Donor Count3
Polar Surface Area111.9 Ų
Rotatable Bond Count4
Physiological Charge-3
Formal Charge0
Refractivity35.23 m³·mol⁻¹
Polarizability14.16

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