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Identification
NamePalmitic Acid
Accession NumberDB03796  (EXPT01393, EXPT02607)
TypeSmall Molecule
GroupsExperimental
Description

A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Hexyldecanoic AcidNot AvailableNot Available
1-Pentadecanecarboxylic acidNot AvailableNot Available
FATNot AvailableNot Available
HexadecanoateNot AvailableNot Available
Hexadecanoic acidNot AvailableNot Available
Hexadecoic acidNot AvailableNot Available
Hexadecylic acidNot AvailableNot Available
Hexaectylic acidNot AvailableNot Available
PalmitateNot AvailableNot Available
Palmitinic acidNot AvailableNot Available
PalmitinsaeureNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number57-10-3
WeightAverage: 256.4241
Monoisotopic: 256.240230268
Chemical FormulaC16H32O2
InChI KeyIPCSVZSSVZVIGE-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)
IUPAC Name
hexadecanoic acid
SMILES
CCCCCCCCCCCCCCCC(O)=O
Mass Specshow(10.5 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassFatty Acids and Conjugates
SubclassStraight Chain Fatty Acids
Direct parentStraight Chain Fatty Acids
Alternative parentsPolyamines; Enolates; Carboxylic Acids
Substituentsenolate; polyamine; carboxylic acid; carboxylic acid derivative
Classification descriptionThis compound belongs to the straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
Pharmacology
IndicationNot Available
PharmacodynamicsPalmitic 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 actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAcute oral toxicity (LD50) in rat is >10000 mg/kg
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9888
Blood Brain Barrier + 0.9488
Caco-2 permeable + 0.8326
P-glycoprotein substrate Non-substrate 0.6321
P-glycoprotein inhibitor I Non-inhibitor 0.9598
P-glycoprotein inhibitor II Non-inhibitor 0.9277
Renal organic cation transporter Non-inhibitor 0.9266
CYP450 2C9 substrate Non-substrate 0.7886
CYP450 2D6 substrate Non-substrate 0.8956
CYP450 3A4 substrate Non-substrate 0.6982
CYP450 1A2 substrate Inhibitor 0.8326
CYP450 2C9 substrate Non-inhibitor 0.8808
CYP450 2D6 substrate Non-inhibitor 0.9554
CYP450 2C19 substrate Non-inhibitor 0.9578
CYP450 3A4 substrate Non-inhibitor 0.9484
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9647
Ames test Non AMES toxic 0.9865
Carcinogenicity Non-carcinogens 0.6452
Biodegradation Ready biodegradable 0.8795
Rat acute toxicity 1.3275 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9322
hERG inhibition (predictor II) Non-inhibitor 0.8868
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point61.8 °CPhysProp
boiling point351.5 °CPhysProp
water solubility0.04 mg/L (at 25 °C)ROBB.ID (1966)
logP7.17SANGSTER (1993)
logS-6.81ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.000407ALOGPS
logP7.23ALOGPS
logP6.26ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.08 m3·mol-1ChemAxon
Polarizability34.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
References
Synthesis Reference

Walter R. Fehr, Earl G. Hammond, “Elevated palmitic acid production in soybeans.” U.S. Patent US5750846, issued February, 1997.

US5750846
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD05341
KEGG CompoundC00249
PubChem Compound985
PubChem Substance46506400
ChEBI15756
ChEMBL
IUPHAR1055
Guide to Pharmacology1055
HETPLM
WikipediaPalmitic_Acid
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(73 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glycodelin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Glycodelin P09466 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Hepatocyte nuclear factor 4-gamma Q14541 Details

3. Lipid binding protein

Kind: protein

Organism: Geobacillus stearothermophilus

Pharmacological action: unknown

Components

Name UniProt ID Details
Lipid binding protein P83812 Details

4. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Trafficking protein particle complex subunit 3 O43617 Details

6. Fatty acid-binding protein TM_1468

Kind: protein

Organism: Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Fatty acid-binding protein TM_1468 Q9X1H9 Details

7. Rhodopsin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Rhodopsin P08100 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
SEC14-like protein 2 O76054 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Palmitoyl-protein thioesterase 1 P50897 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Myelin P2 protein P02689 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-lactalbumin P00709 Details

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

Carriers

1. Fatty acid-binding protein, adipocyte

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Fatty acid-binding protein, adipocyte P15090 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Fatty acid-binding protein, epidermal Q01469 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Fatty acid-binding protein, heart P05413 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Fatty acid-binding protein, intestinal P12104 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

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

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:22