Common NameL-2-aminohexanoate
DescriptionL-Norleucine, also known as L-aminohexanoate or caprine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Thus, L-norleucine is considered to be a fatty acid lipid molecule. An unnatural amino acid that is used experimentally to study protein structure and function. L-Norleucine is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. L-Norleucine exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, L-Norleucine has been detected, but not quantified in cow milk. This could make L-norleucine a potential biomarker for the consumption of these foods. It binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin.
Structure
Molecular FormulaC6H13NO2
Average Mass131.17290
Monoisotopic Mass131.09463
IUPAC Name(2S)-2-aminohexanoic acid
Traditional NameNorleucine
CAS Registry Number327-57-1
SMILESCCCC[C@H]([NH3+])C(=O)[O-]
InChI IdentifierInChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
InChI KeyLRQKBLKVPFOOQJ-YFKPBYRVSA-N
CHEBI IDCHEBI:58455
HMDB IDHMDB0001645
StateSolid
Water Solubility8.91e+01 g/l
logP-1.74
logS-0.17
pKa (Strongest Acidic)2.79
pKa (Strongest Basic)9.53
Hydrogen Acceptor Count3
Hydrogen Donor Count2
Polar Surface Area63.32 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity34.22 m³·mol⁻¹
Polarizability14.46

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