Structure Database (LMSD)

Common Name
alpha-hydroxy lauric acid
Systematic Name
2-hydroxy-dodecanoic acid
Synonyms
LM ID
LMFA01050036
Formula
C12H24O3
Exact Mass
Calculate m/z
216.172545
Sum Composition
FA 12:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]

Biological Context

2-hydroxy Lauric acid is a naturally occuring hydroxylated fatty acid that is found in Acinetobacter species.1 It acts as a partial agonist of free fatty acid receptor 1 (FFAR1/GPR40) and GPR84 receptors in vitro (EC50s = 6.7 and 12.8 μM, respectively).2 2-hydroxy Lauric acid also inhibits bovine hepatic ligase (Ki = 4.4 μM) and mouse kidney mitochondrial medium-chain acyl-CoA synthetase by 48% at a concentration of 40 μM.3 [Matreya, LLC. Catalog No. 1701]

This information has been provided by Cayman Chemical

References

1. Barrientos, L., Marin-Esteban, V., de Chaisemartin, L., et al. An improved strategy to recover large fragments of functional human neutrophil extracellular traps. Front. Immunol. 4(166), 1-10 (2013).
2. Moss, C.W., Wallace, P.L., Hollis, D.G., et al. Cultural and chemical characterization of CDC groups EO-2, M-5, and M-6, Moraxella (Moraxella) species, Oligella urethralis, Acinetobacter species, and Psychrobacter immobilis. J. Clin. Microbiol. 26(3), 484-492 (1988).
3. Kaspersen, M.H., Jenkins, L., Dunlop, J., et al. Succinct synthesis of saturated hydroxy fatty acids and in vitro evaluation of all hydroxylauric acids on FFA1, FFA4, and GPR84. Med. Chem. Commun. 8(6), 1360-1365 (2017).

String Representations

InChiKey (Click to copy)
YDZIJQXINJLRLL-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-10-11(13)12(14)15/h11,13H,2-10H2,1H3,(H,14,15)
SMILES (Click to copy)
C(CCCCCCCCC)C(O)C(=O)O

Other Databases

CHEBI ID
36211
LIPIDBANK ID
DFA0302
PubChem CID
97783
Cayman ID
24586
GuidePharm ID
5849

Calculated Physicochemical Properties

Heavy Atoms 15
Rings 0
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 239.89
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 3.25
Molar Refractivity 61.38

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Updated at
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