PALMITIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H32O2
Molecular Weight	256.4241
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCCCCCC(O)=O

InChI

InChIKey=IPCSVZSSVZVIGE-UHFFFAOYSA-N

InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26393565
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12496284 | https://www.ncbi.nlm.nih.gov/pubmed/14717706 | https://www.ncbi.nlm.nih.gov/pubmed/18511927 | https://www.ncbi.nlm.nih.gov/pubmed/23406428

Palmitic acid is a saturated fatty acid, the principal constituent of refined palm oil, present in the diet and synthesized endogenously. Palmitic acid is able to activate the orphan G protein-coupled receptor GPR40. Palmitic acid was also a weak ligand of peroxisome proliferator-activated receptor gamma. Palmitic acid is a ligand of lipid chaperones - the fatty acid-binding proteins (FABPs). Dietary palm oil and palmitic acid may play a role in the development of obesity, type 2 diabetes mellitus, cardiovascular diseases and cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Free fatty acid receptor 1 10 Target ID: CHEMBL4422 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12496284	Agonist 2678	5.3 null [pEC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14717706	Binding Agent 1064	156.0 µM [Kd]
Fatty acid binding protein muscle 4 Target ID: CHEMBL3344 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18511927 \| https://www.ncbi.nlm.nih.gov/pubmed/2751678	Binding Agent 1064
Fatty acid binding protein adipocyte 12 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18511927 \| https://www.ncbi.nlm.nih.gov/pubmed/2751678	Binding Agent 1064
Fatty acid binding protein epidermal 4 Target ID: CHEMBL3674 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18511927 \| https://www.ncbi.nlm.nih.gov/pubmed/2751678	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Respiratory distress syndrome in premature infants 5 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021746s000lbl.pdf	Preventing		Approved 8429	SURFAXIN Approved Use SURFAXIN is indicated for the prevention of respiratory distress syndrome (RDS) in premature infants at high risk for RDS. Launch Date 2012

PubMed

Title	Date	PubMed
Fatty acid and triglyceride composition of milk fat from lactating Holstein cows in response to supplemental canola oil.	2001 Apr	11352169
Effect of gamma-butyrobetaine on fatty liver in juvenile visceral steatosis mice.	2001 Apr	11341370
Identification of fatty acid molecules in a Fasciola hepatica immunoprophylactic fatty acid-binding protein.	2001 Apr	11318577
Effects of authentic and VLDL hydrolysis-derived fatty acids on vascular smooth muscle cell growth.	2001 Apr	11309244
Carotenoid esters in vegetables and fruits: a screening with emphasis on beta-cryptoxanthin esters.	2001 Apr	11308368
Uncoupling protein 2: a possible link between fatty acid excess and impaired glucose-induced insulin secretion?	2001 Apr	11289045
Pulmonary surfactant protein SP-B is significantly more immunoreactive in anionic than in zwitterionic bilayers.	2001 Apr 13	11311247
Thioacylation is required for targeting G-protein subunit G(o1alpha) to detergent-insoluble caveolin-containing membrane domains.	2001 Apr 15	11284718
Regulation of surfactant-like particle secretion by Caco-2 cells.	2001 Apr 2	11286980
Tolerance induction by acylated peptides: suppression of EAE in the mouse with palmitoylated PLP peptides.	2001 Apr 2	11282157
Kinetics of the lipase-catalyzed synthesis of glucose esters in acetone.	2001 Apr 20	11255158
Plasma membrane localization of palmitoylated tubulin.	2001 Apr 27	11322765
Induction of apoptosis through B-cell receptor cross-linking occurs via de novo generated C16-ceramide and involves mitochondria.	2001 Apr 27	11278517
Participation of carnitine palmitoyltransferase in the synthesis of dipalmitoylphosphatidylcholine in rat alveolar type II cells.	2001 Feb	11330841
A stearic acid-rich diet improves thrombogenic and atherogenic risk factor profiles in healthy males.	2001 Feb	11305631
Fatty acid-induced apoptosis in neonatal cardiomyocytes: redox signaling.	2001 Feb	11291600
Lipotoxicity of the pancreatic beta-cell is associated with glucose-dependent esterification of fatty acids into neutral lipids.	2001 Feb	11272142
Myocardial fatty acid oxidation in patients with impaired glucose tolerance.	2001 Feb	11270674
Effect of fatty acids on phase behavior of hydrated dipalmitoylphosphatidylcholine bilayer: saturated versus unsaturated fatty acids.	2001 Feb	11269932
L-carnitine reduces malondialdehyde concentrations in isolated rat hearts in dependence on perfusion conditions.	2001 Jan	11269669
Insulin inhibits peroxisomal fatty acid oxidation in isolated rat hepatocytes.	2001 Jun	11356722
Systemic and regional free fatty acid metabolism in type 2 diabetes.	2001 Jun	11350782
Demonstration of direct effects of growth hormone on neonatal cardiomyocytes.	2001 Jun 22	11303022
Gbeta gamma isoforms selectively rescue plasma membrane localization and palmitoylation of mutant Galphas and Galphaq.	2001 Jun 29	11294873
Anaerobic biodegradation of alkanes by enriched consortia under four different reducing conditions.	2001 Mar	11349845
Optimization of methods and treatment conditions for studying effects of fatty acids on cell growth.	2001 Mar	11337987
Effects of diets enriched in n-6 or n-3 fatty acids on cholesterol metabolism in older rats chronically fed a cholesterol-enriched diet.	2001 Mar	11337981
Brain and hippocampus fatty acid composition in phospholipid classes of aged-relative cognitive deficit rats.	2001 Mar	11334555
Gas chromatographic analysis of total fatty acids in cider.	2001 Mar	11312846
Modelling of hexadecane degradation in continuous-flow cultures.	2001 Mar	11311466
Effects of antiinflammatory triterpenes isolated from Leptadenia hastata latex on keratinocyte proliferation.	2001 Mar	11268112
Expression of rat liver long-chain acyl-CoA synthetase and characterization of its role in the metabolism of R-ibuprofen and other fatty acid-like xenobiotics.	2001 Mar 15	11266649
Regulation of G proteins by covalent modification.	2001 Mar 26	11313912
Continuous fatty acid oxidation and reduced fat storage in mice lacking acetyl-CoA carboxylase 2.	2001 Mar 30	11283375
[Branched alkanes and other apolar compounds produced by the cyanobacterium Microcoleus vaginatus from the Negev desert].	2001 Mar-Apr	11357397
Thiazolidinediones increase plasma-adipose tissue FFA exchange capacity and enhance insulin-mediated control of systemic FFA availability.	2001 May	11334421
Chronic valproate treatment decreases the in vivo turnover of arachidonic acid in brain phospholipids: a possible common effect of mood stabilizers.	2001 May	11331408
Heparin-induced release of protein-bound solutes during hemodialysis is an in vitro artifact.	2001 May	11325895
Effects of lung surfactant proteins, SP-B and SP-C, and palmitic acid on monolayer stability.	2001 May	11325728
Effects of free fatty acids on beta-cell functions: a possible involvement of peroxisome proliferator-activated receptors alpha or pancreatic/duodenal homeobox.	2001 May	11319727
Imaging of monolayers composed of palmitic acid and lung surfactant protein B.	2001 May	11309099
The sites for fatty acylation, phosphorylation and intermolecular disulphide bond formation of influenza C virus CM2 protein.	2001 May	11297683
A high-sucrose diet increases gluconeogenic capacity in isolated periportal and perivenous rat hepatocytes.	2001 May	11287351
n-6 and n-3 polyunsaturated fatty acids differentially modulate oncogenic Ras activation in colonocytes.	2001 May	11287318
Palmitoylation of caveolin-1 in endothelial cells is post-translational but irreversible.	2001 May 11	11278313
Identification and quantitation of unique fatty acid oxidation products in human atherosclerotic plaque using high-performance liquid chromatography.	2001 May 15	11355856
Differential palmitoylation of two mouse glutamate receptor interacting protein 1 forms with different N-terminal sequences.	2001 May 18	11335060
Biochemical characterization of the reverse activity of rat brain ceramidase. A CoA-independent and fumonisin B1-insensitive ceramide synthase.	2001 May 18	11278489
Physiological levels of mammalian uncoupling protein 2 do not uncouple yeast mitochondria.	2001 May 25	11278935
Palmitate-induced apoptosis can occur through a ceramide-independent pathway.	2001 May 4	11278654

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The conditioned media from palmitic acid (0.2 mM) treated rat cortical astroglia, but not the cerebellar astroglia, significantly elevated levels of phosphorylated tau and BACE1 in cortical neurons as compared to controls

Name

Type

Language

PALMITIC ACID

Official Name

English

SURFAXIN COMPONENT PALMITIC ACID

Brand Name

English

HYDROFOL ACID 1690

Code

English

PALMITIC ACID [USAN]

Common Name

English

KORTACID 1698

Code

English

PALMITATE

Common Name

English

N-HEXADECANOIC ACID

Common Name

English

PALMITIC ACID [FHFI]

Common Name

English

PALMITIC ACID [FCC]

Common Name

English

PALMITIC ACID [USP-RS]

Common Name

English

1-PENTADECANECARBOXYLIC ACID

Systematic Name

English

PALMITIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]

Common Name

English

PALMITIC ACID (CONSTITUENT OF SPIRULINA) [DSC]

Common Name

English

HEXADECANOIC ACID

Systematic Name

English

CETYL ACID [VANDF]

Common Name

English

PALMITIC ACID [EP MONOGRAPH]

Common Name

English

CETYLIC ACID

Common Name

English

PALMITIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL) [DSC]

Common Name

English

IMEX C 1498

Code

English

PALMITIC ACID [INCI]

Common Name

English

PALMITIC ACID [DSC]

Common Name

English

LOXIOL EP 278

Code

English

FEMA NO. 2832

Code

English

NSC-5030

Code

English

PALMITIC ACID [MI]

Common Name

English

CETYL ACID

Common Name

English

PALMITIC ACID [HSDB]

Common Name

English

PRIFAC-2960

Common Name

English

PALMITIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]

Common Name

English

PRISTERENE-4934

Common Name

English

PALMITIC ACID [MART.]

Common Name

English

PALMITIC ACID [II]

Common Name

English

PALMITIC ACID [VANDF]

Common Name

English

Palmitic acid [WHO-DD]

Common Name

English

EDENOR C 16-98-100

Code

English

PALMITIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]

Common Name

English

LUCINACTANT COMPONENT PALMITIC ACID

Common Name

English

Classification Tree Code System Code

LOINC

47641-6