Structure Database (LMSD)
Common Name
Leucinic acid
Systematic Name
2-hydroxy-4-methyl-pentanoic acid
Synonyms
3D model of Leucinic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
2-Hydroxyisocaproic acid is a metabolite of L-leucine catabolism.1,2,3,4,5 It is formed from L-leucine via an α-ketoisocaproic acid intermediate by hydroxyisocaproic acid dehydrogenase in L. lactis.1 2-Hydroxyisocaproic acid is active against a variety of Gram-positive and -negative bacteria (IC50s = 0.6-4.5 mg/ml) and several Candida species (IC50s = 18-36 mg/ml).2,3 Dietary administration of 2-hydroxyisocaproic acid (50.4 g/kg) also prevents reductions in protein synthesis during the immobilization period and increases protein synthesis and muscle mass during the recovery period in casted animals in a rat model of immobilization-induced muscle atrophy.4
This information has been provided by Cayman Chemical
References
1. Park, B., Hwang, H., Chang, J.Y., et al. Identification of 2-hydroxyisocaproic acid production in lactic acid bacteria and evaluation of microbial dynamics during kimchi ripening. Sci. Rep. 7(1), 10904 (2017).
2. Sakko, M.T., L., Sorsa, T., Hietala, P., et al. 2-Hydroxyisocaproic acid (HICA): A new potential topical antibacterial agent. Int. J. Antimicrob. Agents 39(6), 539-540 (2012).
String Representations
InChiKey (Click to copy)
LVRFTAZAXQPQHI-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
SMILES (Click to copy)
C(=O)(O)C(O)CC(C)C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
9
Rings
0
Aromatic Rings
0
Rotatable Bonds
3
Van der Waals Molecular Volume
136.09
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
0.76
Molar Refractivity
33.61
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Updated at
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