U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H31BrO2
Molecular Weight 335.32
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-BROMOPALMITIC ACID

SMILES

CCCCCCCCCCCCCCC(Br)C(O)=O

InChI

InChIKey=DPRAYRYQQAXQPE-UHFFFAOYSA-N
InChI=1S/C16H31BrO2/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)

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
In Vitro and In Vivo Characterizations of Chiglitazar, a Newly Identified PPAR Pan-Agonist.
2012
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.
2011-08
Acyl-protein thioesterase 2 catalyzes the deacylation of peripheral membrane-associated GAP-43.
2010-11-30
Palmitate and insulin synergistically induce IL-6 expression in human monocytes.
2010-11-05
Palmitoylation of the S0-S1 linker regulates cell surface expression of voltage- and calcium-activated potassium (BK) channels.
2010-10-22
Palmitoylation of human FasL modulates its cell death-inducing function.
2010-10-21
Palmitoylation and function of glial glutamate transporter-1 is reduced in the YAC128 mouse model of Huntington disease.
2010-10
Palmitic acid analogs exhibit nanomolar binding affinity for the HIV-1 CD4 receptor and nanomolar inhibition of gp120-to-CD4 fusion.
2010-08-13
Localized fetomaternal hyperglycemia: spatial and kinetic definition by positron emission tomography.
2010-08-06
Multiple palmitoyltransferases are required for palmitoylation-dependent regulation of large conductance calcium- and voltage-activated potassium channels.
2010-07-30
Eicosapentaenoic acid inhibits endothelial cell migration in vitro.
2010-07-09
Interplay of palmitoylation and phosphorylation in the trafficking and localization of phosphodiesterase 10A: implications for the treatment of schizophrenia.
2010-07-07
Mice with alopecia, osteoporosis, and systemic amyloidosis due to mutation in Zdhhc13, a gene coding for palmitoyl acyltransferase.
2010-06-10
Rapid and selective detection of fatty acylated proteins using omega-alkynyl-fatty acids and click chemistry.
2010-06
Golgi-specific DHHC zinc finger protein GODZ mediates membrane Ca2+ transport.
2010-02-12
Palmitoylation supports the association of tetraspanin CD63 with CD9 and integrin alphaIIbbeta3 in activated platelets.
2010-02
Role of GD3-CLIPR-59 association in lymphoblastoid T cell apoptosis triggered by CD95/Fas.
2010-01-05
Membrane-initiated estradiol signaling increases tyrosine hydroxylase promoter activity with ER alpha in PC12 cells.
2010-01
The C-terminal sequence of RhoB directs protein degradation through an endo-lysosomal pathway.
2009-12-02
Reversible, temperature-dependent supramolecular assembly of aquaporin-4 orthogonal arrays in live cell membranes.
2009-12-02
Molecular mechanism of recombinant liver fatty acid binding protein's antioxidant activity.
2009-12
Role of PSD95 in membrane association and catalytic activity of nNOSalpha in nitrergic varicosities in mice gut.
2009-10
Neuroligin1: a cell adhesion molecule that recruits PSD-95 and NMDA receptors by distinct mechanisms during synaptogenesis.
2009-05-18
Fatty acid acylation regulates trafficking of the unusual Plasmodium falciparum calpain to the nucleolus.
2009-04
The effects of 2-bromopalmitate on the fatty acid composition in differentiating adipocytes of red sea bream (Pagrus major).
2009-04
2-Bromopalmitate and 2-(2-hydroxy-5-nitro-benzylidene)-benzo[b]thiophen-3-one inhibit DHHC-mediated palmitoylation in vitro.
2009-02
PPAR/RXR Regulation of Fatty Acid Metabolism and Fatty Acid omega-Hydroxylase (CYP4) Isozymes: Implications for Prevention of Lipotoxicity in Fatty Liver Disease.
2009
Protein palmitoylation regulates osteoblast differentiation through BMP-induced osterix expression.
2009
Huntingtin-interacting proteins, HIP14 and HIP14L, mediate dual functions, palmitoyl acyltransferase and Mg2+ transport.
2008-11-28
Molecular characterization of peroxisome proliferator-activated receptors (PPARs) and their gene expression in the differentiating adipocytes of red sea bream Pagrus major.
2008-11
Endogenous peroxisome proliferator-activated receptor-gamma augments fatty acid uptake in oxidative muscle.
2008-11
Mesodermal fate decisions of a stem cell: the Wnt switch.
2008-09
Long chain fatty acid uptake in vivo: comparison of [125I]-BMIPP and [3H]-bromopalmitate.
2008-08
Polyunsaturated fatty acids block platelet-activating factor-induced phosphatidylinositol 3 kinase/Akt-mediated apoptosis in intestinal epithelial cells.
2008-05
Excitotoxic loss of post-synaptic sites is distinct temporally and mechanistically from neuronal death.
2008-01
Palmitoylation of POTE family proteins for plasma membrane targeting.
2007-11-23
R7-binding protein targets the G protein beta 5/R7-regulator of G protein signaling complex to lipid rafts in neuronal cells and brain.
2007-09-19
The role of an intracellular cysteine stretch in the sorting of the type II Na/phosphate cotransporter.
2007-09
Structural and functional analysis of the apoptosis-associated tyrosine kinase (AATYK) family.
2007-08-24
Shuttling of G protein subunits between the plasma membrane and intracellular membranes.
2007-08-17
Mechanisms involved in the cytotoxic and cytoprotective actions of saturated versus monounsaturated long-chain fatty acids in pancreatic beta-cells.
2007-08
Role of LRAT on the retinoid isomerase activity and membrane association of Rpe65.
2007-07-20
Regulation of FAT/CD36 mRNA gene expression by long chain fatty acids in the differentiated 3T3-L1 cells.
2007-07
S-acylation regulates Kv1.5 channel surface expression.
2007-07
Activation of protein phosphatase 2A by palmitate inhibits AMP-activated protein kinase.
2007-03-30
Multiple peroxisome proliferator-activated receptor beta subtypes from Atlantic salmon (Salmo salar).
2007-03
Malonyl coenzyme A affects insulin-stimulated glucose transport in myotubes.
2007-02
Metabolic Functions of Peroxisome Proliferator-Activated Receptor beta/delta in Skeletal Muscle.
2007
Homeostatic plasticity during alcohol exposure promotes enlargement of dendritic spines.
2006-12
Regulation of rat liver apolipoprotein A-I, apolipoprotein A-II and acyl-coenzyme A oxidase gene expression by fibrates and dietary fatty acids.
1995-08-15
Patents
Name Type Language
2-BROMOPALMITIC ACID
Systematic Name English
NSC-58378
Preferred Name English
2-BROMO-N-HEXADECANOIC ACID
Common Name English
2-BROMOHEXADECANOIC ACID
Systematic Name English
.ALPHA.-BROMOPALMITIC ACID
Systematic Name English
HEXADECANOIC ACID, 2-BROMO-
Systematic Name English
1-BROMOPENTADECANECARBOXYLIC ACID
Systematic Name English
DL-2-BROMOPALMITATE
Common Name English
2-BROMOPALMITATE
Systematic Name English
Code System Code Type Description
CAS
18263-25-7
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY
FDA UNII
7EI4G5X28Z
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY
CHEBI
133152
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY
PUBCHEM
82145
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID0037734
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY
NSC
58378
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY
ECHA (EC/EINECS)
242-137-0
Created by admin on Mon Mar 31 22:20:50 GMT 2025 , Edited by admin on Mon Mar 31 22:20:50 GMT 2025
PRIMARY