You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameStearic acid
Accession NumberDB03193  (EXPT02965)
TypeSmall Molecule
GroupsExperimental
Description

Stearic acid (IUPAC systematic name: octadecanoic acid) is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Heptadecanecarboxylic acidNot AvailableNot Available
Cetylacetic acidNot AvailableNot Available
Fatty acids C16-18Not AvailableNot Available
Isooctadecanoic acidNot AvailableNot Available
Isostearic acidNot AvailableNot Available
N-octadecanoic aciddNot AvailableNot Available
Octadecanoic acidNot AvailableNot Available
OctadecansaeureNot AvailableNot Available
Octadecoic acidNot AvailableNot Available
OLANot AvailableNot Available
StearateNot AvailableNot Available
StearinsaeureNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Bonderlube 235Not Available
C-Lube 10Not Available
DermaroneNot Available
Emersol 153NFNot Available
Flexichem BNot Available
HystreneNot Available
IndustreneNot Available
LunacNot Available
Prifac 2918Not Available
ProdhygineNot Available
Brand mixtures
Brand NameIngredients
Borage OilCis-Linoleic Acid + Gamma-Linolenic Acid + Oleic Acid + Palmitic Acid + Stearic Acid
SaltsNot Available
Categories
CAS number57-11-4
WeightAverage: 284.4772
Monoisotopic: 284.271530396
Chemical FormulaC18H36O2
InChI KeyQIQXTHQIDYTFRH-UHFFFAOYSA-N
InChI
InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
IUPAC Name
octadecanoic acid
SMILES
CCCCCCCCCCCCCCCCCC(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
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAcute oral toxicity (LD50): 4640 mg/kg [Rat]. Acute dermal toxicity (LD50): >5000 mg/kg [Rabbit].
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Plasmalogen SynthesisMetabolicSMP00479
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsMetabolicSMP00482
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 point68.8 °CPhysProp
boiling point383 °CPhysProp
water solubility0.597 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP8.23SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility6.61e-05 mg/mLALOGPS
logP8.02ALOGPS
logP7.15ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity86.29 m3·mol-1ChemAxon
Polarizability38.64 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraGC-MSMS/MSMS1D NMR2D NMR
References
Synthesis Reference

Arnold W. Fogel, “12-hydroxy stearic acid esters, compositions based upon same and methods of using and making such compositions.” U.S. Patent US5993861, issued July, 1998.

US5993861
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Group IID secretory phospholipase A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Group IID secretory phospholipase A2 Q9UNK4 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

Carriers

1. 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. 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

2. 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. Spector AA, John K, Fletcher JE: Binding of long-chain fatty acids to bovine serum albumin. J Lipid Res. 1969 Jan;10(1):56-67. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:20