Structure Database (LMSD)
Common Name
2-Hydroxymyristic acid
Systematic Name
2-hydroxytetradecanoic acid
Synonyms
3D model of 2-Hydroxymyristic 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-hydroxy Myristic acid is a hydroxy fatty acid that has been found in bovine, human, and horse milk, cow and buffalo cheeses, sea bass filet, seal oil, human vernix caseosa, and wool wax.1 It inhibits cleavage between the enterovirus capsid proteins VP4 and VP2, a process required for enterovirus infectivity, as well as Junin and Tacaribe viral replication (IC50s = 20.1 and 14.2 μM, respectively).2,3 2-hydroxy Myristic acid was previously characterized as a weak inhibitor of peptide myristoylation (Ki = 200 μM) but has been shown to be inactive in ARL1 cells when used at 100 μM.4,5 [Matreya, LLC. Catalog No. 1703]
This information has been provided by Cayman Chemical
References
1. Jenske, R., and Vetter, W. Concentrations of medium-chain 2- and 3-hydroxy fatty acids in foodstuffs. Food Chem. 114(3), 1122-1129 (2009).
3. Tan, Y.W., Hong, W.J., and Chu, J.J. Inhibition of enterovirus VP4 myristoylation is a potential antiviral strategy for hand, foot and mouth disease. Antiviral Res. 133, 191-195 (2016).
4. Cordo, S.M., Candurra, N.A., and Damonte, E.B. Myristic acid analogs are inhibitors of Junin virus replication. Microbes Infect. 1(8), 609-614 (1999).
String Representations
InChiKey (Click to copy)
JYZJYKOZGGEXSX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-12-13(15)14(16)17/h13,15H,2-12H2,1H3,(H,16,17)
SMILES (Click to copy)
C(C(O)CCCCCCCCCCCC)(O)=O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
17
Rings
0
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
274.49
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
4.03
Molar Refractivity
70.62
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Updated at
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