Structure Database (LMSD)
Common Name
2-chloro-palmitic acid
Systematic Name
2-chlorohexadecanoic acid
Synonyms
- 2-ClHOH
LM ID
LMFA01090046
Formula
C16H31ClO2
Exact Mass
Calculate m/z
290.201258
Status
Curated
3D model of 2-chloro-palmitic 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-chloro Palmitic acid is a monochlorinated form of palmitic acid . It is produced in a myeloperoxidase (MPO) and time-dependent manner in neutrophils stimulated by phorbol 12-myristate 13-acetate (PMA). 2-chloro Palmitic acid (10 μM) induces neutrophil extracellular trap (NET) formation (NETosis) in human neutrophils, increasing DNA release from neutrophils, colocalization of MPO with extracellular DNA (ecDNA), and trapping of E. coli.1 It increases COX-2 protein levels in human coronary artery endothelial cells (HCAECs) when used at a concentration of 50 μM and increases production of P-selectin, von Willebrand factor, and angiopoietin-2 in HCAECs, as well as neutrophil and platelet adherence, when used at a concentration of 10 μM.2,3 2-chloro Palmitic acid (10-50 μM) also induces apoptosis in THP-1 cells and primary human monocytes and increases caspase-3 activity in THP-1 cells.4
This information has been provided by Cayman Chemical
References
1. Wang, W.Y., Albert, C.J., and Ford, D.A. α-Chlorofatty acid accumulates in activated monocytes and causes apoptosis through reactive oxygen species production and endoplasmic reticulum stress. Arterioscler. Thromb. Vasc. Biol. 34(3), 526-532 (2014).
3. Messner, M.C., Albert, C.J., and Ford, D.A. 2-Chlorohexadecanal and 2-chlorohexadecanoic acid induce COX-2 expression in human coronary artery endothelial cells. Lipids 43(7), 581-588 (2008).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Chlorinated lipid species in activated human neutrophils: lipid metabolites of 2-chlorohexadecanal.,
J Lipid Res, 2010
J Lipid Res, 2010
Pubmed ID:
20019386
DOI:
10.1194/jlr.M003673
String Representations
InChiKey (Click to copy)
LDQUHRSWFMWRNG-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H31ClO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15H,2-14H2,1H3,(H,18,19)
SMILES (Click to copy)
C(Cl)(CCCCCCCCCCCCCC)C(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
315.51
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
6.06
Molar Refractivity
83.48
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Updated at
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