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Identification
Name Palmitic Acid
Accession Number DB03796 (EXPT01393, EXPT02607)
Type small molecule
Groups experimental
Description

A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
1-Hexyldecanoic Acid
1-Pentadecanecarboxylic acid
FAT
Hexadecanoate
Hexadecanoic acid
Hexadecoic acid
Hexadecylic acid
Hexaectylic acid
Palmitate
Palmitinic acid
Palmitinsaeure
First Prev Next Last
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Enzyme Inhibitors
CAS number 57-10-3
Weight Average: 256.4241
Monoisotopic: 256.240230268
Chemical Formula C16H32O2
InChI Key InChIKey=IPCSVZSSVZVIGE-UHFFFAOYSA-N
InChI
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)
Plain Text
IUPAC Name
hexadecanoic acid
SMILES
CCCCCCCCCCCCCCCC(O)=O
Plain Text
Mass Spec show (10.5 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Acute oral toxicity (LD50) in rat is >10000 mg/kg
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 61.8 °C PhysProp
boiling point 351.5 °C PhysProp
water solubility 0.04 mg/L (at 25 °C) ROBB.ID (1966)
logP 7.17 SANGSTER (1993)
logS -6.81 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 4.07e-04 g/l ALOGPS
logP 7.23 ALOGPS
logP 6.26 ChemAxon
logS -5.8 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 37.3 ChemAxon
rotatable bond count 14 ChemAxon
refractivity 77.08 ChemAxon
polarizability 34.36 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D05341 Link_out
KEGG Compound C00249 Link_out
PubChem Compound 985 Link_out
PubChem Substance 46506400 Link_out
ChEBI 15756 Link_out
ChEMBL 15756 Link_out
IUPHAR 1055 Link_out
Guide to Pharmacology 1055 Link_out
HET PLM Link_out
Wikipedia http://en.wikipedia.org/wiki/Palmitic_Acid Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (73 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Glycodelin

Pharmacological action: unknown

This protein is, quantitatively, the main protein synthesized and secreted in the endometrium from mid-luteal phase of the menstrual cycle and during the first semester of pregnancy

Organism class: human
UniProt ID: P09466 Link_out
Gene: PAEP Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Hepatocyte nuclear factor 4-gamma

Pharmacological action: unknown

Transcription factor. Has a lower transcription activation potential than HNF4-alpha

Organism class: human
UniProt ID: Q14541 Link_out
Gene: HNF4G
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

3. Lipid binding protein

Pharmacological action: unknown
Organism class: bacterial
UniProt ID: P83812 Link_out
Protein Sequence: FASTA

4. Cytochrome P450 2C8

Pharmacological action: unknown

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti- cancer drug paclitaxel (taxol)

Organism class: human
UniProt ID: P10632 Link_out
Gene: CYP2C8
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Schoch GA, Yano JK, Wester MR, Griffin KJ, Stout CD, Johnson EF: Structure of human microsomal cytochrome P450 2C8. Evidence for a peripheral fatty acid binding site. J Biol Chem. 2004 Mar 5;279(10):9497-503. Epub 2003 Dec 15. Pubmed

5. Trafficking protein particle complex subunit 3

Pharmacological action: unknown

May play a role in vesicular transport from endoplasmic reticulum to Golgi

Organism class: human
UniProt ID: O43617 Link_out
Gene: TRAPPC3
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

6. UPF0230 protein TM_1468

Pharmacological action: unknown
Organism class: bacterial
UniProt ID: Q9X1H9 Link_out
Gene: TM_1468
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

7. Rhodopsin

Pharmacological action: unknown

Visual pigments are the light-absorbing molecules that mediate vision. They consist of an apoprotein, opsin, covalently linked to cis-retinal

Organism class: human
UniProt ID: P08100 Link_out
Gene: RHO Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

8. SEC14-like protein 2

Pharmacological action: unknown

Carrier protein. Binds to some hydrophobic molecules and promotes their transfer between the different cellular sites. Binds with high affinity to alpha-tocopherol. Also binds with a weaker affinity to other tocopherols and to tocotrienols. May have a transcriptional activatory activity via its association with alpha-tocopherol. Probably recognizes and binds some squalene structure, suggesting that it may regulate cholesterol biosynthesis by increasing the transfer of squalene to a metabolic active pool in the cell

Organism class: human
UniProt ID: O76054 Link_out
Gene: SEC14L2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

9. Palmitoyl-protein thioesterase 1

Pharmacological action: unknown
Organism class: human
UniProt ID: P50897 Link_out
Gene: PPT1
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

10. Myelin P2 protein

Pharmacological action: unknown

May play a role in lipid transport protein in Schwann cells

Organism class: human
UniProt ID: P02689 Link_out
Gene: PMP2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

11. Alpha-lactalbumin

Pharmacological action: unknown
Organism class: human
UniProt ID: P00709 Link_out
Gene: LALBA
SNPs: SNPJam Report Link_out

References:
  1. Barbana C, Perez MD, Pocovi C, Sanchez L, Wehbi Z: Interaction of human alpha-lactalbumin with fatty acids: determination of binding parameters. Biochemistry (Mosc). 2008 Jun;73(6):711-6. Pubmed
Transporters

1. Multidrug resistance protein 1

Actions: inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Konishi T, Satsu H, Hatsugai Y, Aizawa K, Inakuma T, Nagata S, Sakuda SH, Nagasawa H, Shimizu M: Inhibitory effect of a bitter melon extract on the P-glycoprotein activity in intestinal Caco-2 cells. Br J Pharmacol. 2004 Oct;143(3):379-87. Epub 2004 Sep 6. Pubmed
Carriers

1. Fatty acid-binding protein, adipocyte

Lipid transport protein in adipocytes. Binds both long chain fatty acid and retinoic acid

UniProt ID: P15090 Link_out
Gene: FABP4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Fatty acid-binding protein, epidermal

High specificity for fatty acids. Highest affinity for C18 chain length. Decreasing the chain length or introducing double bonds reduces the affinity. May be involved in keratinocyte differentiation

UniProt ID: Q01469 Link_out
Gene: FABP5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Fatty acid-binding protein, heart

FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters

UniProt ID: P05413 Link_out
Gene: FABP3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Zanotti G, Scapin G, Spadon P, Veerkamp JH, Sacchettini JC: Three-dimensional structure of recombinant human muscle fatty acid-binding protein. J Biol Chem. 1992 Sep 15;267(26):18541-50. Pubmed

4. Fatty acid-binding protein, intestinal

FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to unsaturated long- chain fatty acids. FABP2 may also help maintain energy homeostasis by functioning as a lipid sensor

UniProt ID: P12104 Link_out
Gene: FABP2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

5. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Simard JR, Zunszain PA, Hamilton JA, Curry S: Location of high and low affinity fatty acid binding sites on human serum albumin revealed by NMR drug-competition analysis. J Mol Biol. 2006 Aug 11;361(2):336-51. Epub 2006 Jun 30. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:22