Common Name(2s)-2-isopropyl-3-oxosuccinate
Description2-Isopropyl-3-oxosuccinate belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain that contains less than 6 carbon atoms. 2-Isopropyl-3-oxosuccinate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-oxosuccinate exists in all living species, ranging from bacteria to humans. 2-Isopropyl-3-oxosuccinate has been detected, but not quantified in, several different foods, such as garden onion (var.), German camomiles, limes, cloud ear fungus, and citrus. This could make 2-isopropyl-3-oxosuccinate a potential biomarker for the consumption of these foods. 2-Isopropyl-3-oxosuccinate is an intermediate in leucine biosynthesis and can be generated from (2R,3S)-3-isopropylmalate. It is the third step in leucine biosynthesis after the fork from valine synthesis. It is an oxidative decarboxylation. Leucine biosynthesis involves a five-step conversion process starting with the valine precursor 2-keto-isovalerate. The final step in this pathway is catalyzed by two transaminases of broad specificity: branched-chain amino acid transferase (IlvE) and tyrosine aminotransferase (TyrB). In this pathway, 2-isopropyl-3-oxosuccinate is converted into 4-methyl-2-oxopentanoate via a spontaneous reaction (BioCyc).
Structure
Molecular FormulaC7H10O5
Average Mass174.15130
Monoisotopic Mass174.05282
IUPAC Name(3S)-2-oxo-3-(propan-2-yl)butanedioic acid
Traditional Name(2s)-2-isopropyl-3-oxobutanedioic acid
CAS Registry Number1245945-28-1
SMILESCC(C)[C@H](C(=O)[O-])C(=O)C(=O)[O-]
InChI IdentifierInChI=1S/C7H10O5/c1-3(2)4(6(9)10)5(8)7(11)12/h3-4H,1-2H3,(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyHIIZAGQWABAMRR-BYPYZUCNSA-N
CHEBI IDCHEBI:17214
HMDB IDHMDB0012149
StateSolid
Water Solubility7.02e+00 g/l
logP0.43
logS-1.39
pKa (Strongest Acidic)2.93
pKa (Strongest Basic)-9.95
Hydrogen Acceptor Count5
Hydrogen Donor Count2
Polar Surface Area91.67 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity38.06 m³·mol⁻¹
Polarizability15.83

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