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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
Pathways
PathwayCategorySMPDB ID
Fatty Acid Elongation In MitochondriaMetabolicSMP00054
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)DiseaseSMP00544
Glycerol Kinase DeficiencyDiseaseSMP00187
Familial lipoprotein lipase deficiencyDiseaseSMP00530
Glycerolipid MetabolismMetabolicSMP00039
D-glyceric aciduraDiseaseSMP00529
Long chain acyl-CoA dehydrogenase deficiency (LCAD)DiseaseSMP00539
Fatty acid MetabolismMetabolicSMP00051
Very-long-chain acyl coa dehydrogenase deficiency (VLCAD)DiseaseSMP00540
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)DiseaseSMP00235
Carnitine palmitoyl transferase deficiency (I)DiseaseSMP00538
Trifunctional protein deficiencyDiseaseSMP00545
Glutaric Aciduria Type IDiseaseSMP00185
Medium chain acyl-coa dehydrogenase deficiency (MCAD)DiseaseSMP00542
Ethylmalonic EncephalopathyDiseaseSMP00181
Carnitine palmitoyl transferase deficiency (II)DiseaseSMP00541
CHILD SyndromeDiseaseSMP00387
Congenital Bile Acid Synthesis Defect Type IIDiseaseSMP00314
Fluvastatin Action PathwayDrug actionSMP00119
27-Hydroxylase DeficiencyDiseaseSMP00720
DesmosterolosisDiseaseSMP00386
Fatty Acid BiosynthesisMetabolicSMP00456
Congenital Bile Acid Synthesis Defect Type IIIDiseaseSMP00318
Zoledronate Action PathwayDrug actionSMP00107
Atorvastatin Action PathwayDrug actionSMP00131
Cholesteryl ester storage diseaseDiseaseSMP00508
Smith-Lemli-Opitz Syndrome (SLOS)DiseaseSMP00389
Simvastatin Action PathwayDrug actionSMP00082
Rosuvastatin Action PathwayDrug actionSMP00092
Cerebrotendinous Xanthomatosis (CTX)DiseaseSMP00315
Pamidronate Action PathwayDrug actionSMP00117
Wolman diseaseDiseaseSMP00511
Lysosomal Acid Lipase Deficiency (Wolman Disease)DiseaseSMP00319
Ibandronate Action PathwayDrug actionSMP00079
Pravastatin Action PathwayDrug actionSMP00089
Bile Acid BiosynthesisMetabolicSMP00035
Zellweger SyndromeDiseaseSMP00316
Risedronate Action PathwayDrug actionSMP00112
Mevalonic aciduriaDiseaseSMP00510
Steroid BiosynthesisMetabolicSMP00023
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)DiseaseSMP00388
Alendronate Action PathwayDrug actionSMP00095
Familial Hypercholanemia (FHCA)DiseaseSMP00317
HypercholesterolemiaDiseaseSMP00209
Lovastatin Action PathwayDrug actionSMP00099
Cerivastatin Action PathwayDrug actionSMP00111
Hyper-IgD syndromeDiseaseSMP00509
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9888
Blood Brain Barrier+0.9488
Caco-2 permeable+0.8326
P-glycoprotein substrateNon-substrate0.6321
P-glycoprotein inhibitor INon-inhibitor0.9598
P-glycoprotein inhibitor IINon-inhibitor0.9277
Renal organic cation transporterNon-inhibitor0.9266
CYP450 2C9 substrateNon-substrate0.7886
CYP450 2D6 substrateNon-substrate0.8956
CYP450 3A4 substrateNon-substrate0.6982
CYP450 1A2 substrateInhibitor0.8326
CYP450 2C9 substrateNon-inhibitor0.8808
CYP450 2D6 substrateNon-inhibitor0.9554
CYP450 2C19 substrateNon-inhibitor0.9578
CYP450 3A4 substrateNon-inhibitor0.9484
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9865
CarcinogenicityNon-carcinogens0.6452
BiodegradationReady biodegradable0.8795
Rat acute toxicity1.3275 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9322
hERG inhibition (predictor II)Non-inhibitor0.8868
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 Solubility0.000407 mg/mLALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.5 KB)
SpectraGC-MSMS/MSMS1D 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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 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

2. 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

3. 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

4. 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

5. 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

6. Hepatocyte nuclear factor 4-gamma

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

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

7. Lipid binding protein

Kind: protein

Organism: Geobacillus stearothermophilus

Pharmacological action: unknown

Components

Name UniProt ID Details
Lipid binding protein P83812 Details

8. 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

9. 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

10. 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

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. 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

2. 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

3. 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

4. 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

5. 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

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