Structure Database (LMSD)

Common Name
Lauric acid
Systematic Name
dodecanoic acid
Synonyms
  • n-Dodecanoic acid
  • Dodecanoate
  • Dodecylic acid
  • C12:0
  • Laurostearic acid
LM ID
LMFA01010012
Formula
Exact Mass
Calculate m/z
200.17763
Sum Composition
Status
Curated





Classification

Biological Context

Lauric acid is a medium-chain saturated fatty acid. It has been found at high levels in coconut oil.1 Lauric acid induces the activation of NF-κB and the expression of COX-2, inducible nitric oxide synthase (iNOS), and IL-1α in RAW 264.7 cells when used at a concentration of 25 µM.2

This information has been provided by Cayman Chemical

References

1. Lee, J.Y., Sohn, K.H., Rhee, S.H., et al. Saturated fatty acids, but not unsaturated fatty acids, induced the expression of cyclooxygenase-2 mediated through Toll-like receptor 4. J. Biol. Chem. 276(20), 16683-16689 (2001).
2. Laureles, L.R., Rodriguez, F.M., Reaño, C.E., et al. Variability in fatty acid and triacylglycerol composition of the oil of coconut (Cocos nucifera L.) hybrids and their parentals. J. Agric. Food Chem. 50(6), 1581-1586 (2002).

Reactions

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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
POULHZVOKOAJMA-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
SMILES (Click to copy)
C(CC)CCCCCCCCC(=O)O

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0012
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 14
Rings 0
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 231.10
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 3.99
Molar Refractivity 59.48

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Created at
-
Updated at
25th Apr 2022