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

Classification

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
Pubmed ID: 20019386

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

PubChem CID
Cayman ID

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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