Structure Database (LMSD)

Common Name
beta-hydroxylauric acid
Systematic Name
3-hydroxy-dodecanoic acid
Synonyms
LM ID
LMFA01050037
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

3-hydroxy Lauric acid is a hydroxylated fatty acid that is found in bacteria as well as Pseudosuberites and D. calyx sea sponges.1,2,3,4 It has antifungal activity against a panel of seven fungi (MICs = 10-50 μg/ml).3 3-hydroxy Lauric acid acts as a partial agonist of GPR84 receptors in vitro (EC50 = 5.24 μM).5 [Matreya, LLC. Catalog No. 1731]

This information has been provided by Cayman Chemical

References

1. Barnathan, G., Kornprobst, J.-M., Doumenq, P., et al. Sponge fatty acids, 5. Characterization of complete series of 2-hydroxy long-chain fatty acids in phospholipids of two Senegalese marine sponges from the family suberitidae: Pseudosuberites sp. and Suberites massa. J. Nat. Prod. 56(12), 2104-2113 (2004).
2. 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).
3. Kim, M.C., Pak, S.H., Rim, S.G., et al. Luteolibacter arcticus sp. nov., isolated from high Arctic tundra soil, and emended description of the genus Luteolibacter. Int. J. Syst. Evol. Microbiol. 65(Pt. 6), 1922-1928 (2015).
4. Panda, S., Bandyopadhyay, P.K., and Chatterjee, S.N. Characterization of Pseudomonas aeruginosa PB112 (JN996498) isolated from infected Labeo bata (Hamilton) by 16S rRNA gene sequence analysis and fatty acid methyl ester (FAME) analysis. African J. Biotechnol. 12(4), 400-405 (2013).
5. He, R., Wakimoto, T., Egami, Y., et al. Heterologously expressed β-hydroxyl fatty acids from a metagenomic library of a marine sponge. Bioorg. Med. Chem. Lett. 22(24), 7322-7325 (2012).

String Representations

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

Other Databases

HMDB ID
HMDB0000387
CHEBI ID
36206
LIPIDBANK ID
DFA0303
PubChem CID
94216
Cayman ID
24642
GuidePharm ID
5850

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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