Showing Metabocard for (2S)-2-isopropylmalate (BASm0000045)

Common Name	(2s)-2-isopropylmalate
Description	2-Isopropylmalic acid (CAS: 3237-44-3), also known as 3-carboxy-3-hydroxyisocaproic acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. 2-Isopropylmalic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Isopropylmalic acid is an alpha-hydroxy organic acid regularly occurring in the urine of healthy individuals (PMID: 2338430 , 544608 ), and in hemofiltrates (PMID: 7251751 ). 2-Isopropylmalic acid is elevated during fasting and diabetic ketoacidosis (PMID: 1591279 ). It is also a metabolite found in Acetobacter (PMID: 6035258 ).
Structure
Molecular Formula	C₇H₁₂O₅
Average Mass	176.16720
Monoisotopic Mass	176.06847
IUPAC Name	(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid
Traditional Name	2-isopropyl-malic acid
CAS Registry Number	49601-06-01
SMILES	CC(C)[C@@](O)(CC(=O)[O-])C(=O)[O-]
InChI Identifier	InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1
InChI Key	BITYXLXUCSKTJS-ZETCQYMHSA-N
CHEBI ID	CHEBI:1178
HMDB ID	HMDB0000402
State	Solid
Water Solubility	1.81e+02 g/l
logP	-0.29
logS	0.01
pKa (Strongest Acidic)	3.63
pKa (Strongest Basic)	-4.14
Hydrogen Acceptor Count	5
Hydrogen Donor Count	3
Polar Surface Area	94.83 Å²
Rotatable Bond Count	4
Physiological Charge	-2
Formal Charge	0
Refractivity	38.58 m³·mol⁻¹
Polarizability	16.37

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