Structure Database (LMSD)
Common Name
Lauric acid
Systematic Name
dodecanoic acid
Synonyms
- n-Dodecanoic acid
- Dodecanoate
- Dodecylic acid
- C12:0
- Laurostearic acid
3D model of Lauric 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
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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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
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
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
Admin
Created at
-
Updated at
25th Apr 2022