Identification

Name
Stearic acid
Accession Number
DB03193  (EXPT02965)
Type
Small Molecule
Groups
Experimental
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
  • 1-Heptadecanecarboxylic acid
  • Cetylacetic acid
  • Fatty acids C16-18
  • Isooctadecanoic acid
  • Isostearic acid
  • N-octadecanoic acidd
  • Octadecanoic acid
  • Octadecansaeure
  • Octadecoic acid
  • OLA
  • Stearate
  • Stearinsaeure
External IDs
Caswell No. 801D / FEMA No. 3035 / NSC-25956 / NSC-261168
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cellbn First Care CleanserCream16 g/100mLTopicalWorldcostec.co.,ltd2017-05-26Not applicableUs
Dr. G Pore Deep Clearing FoamCream15 g/10mLTopicalGOWOONSESANG COSMETICS CO., LTD.2016-03-01Not applicableUs
Dr.g A-clear FoamCream20 g/100mLTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-05Not applicableUs
Dr.g Hyper Brightening Cleansing FoamCream8 g/100mLTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-05Not applicableUs
Dr.g Red-blemish Moisture Cleansing FoamCream25 g/100mLTopicalGOWOONSESANG COSMETICS CO., LTD.2015-07-05Not applicableUs
Jinhwagwangsu BubbleSoap120 mg/gTopicalC Pbio Co., Ltd2015-06-01Not applicableUs
Jinhwagwangsu HairSoap12 g/100gTopicalC Pbio Co., Ltd2016-01-25Not applicableUs
K Oxiderm OP Post Procedure skin care bruiseCream1 g/100mLTopicalEzekielcosmetic Co., Ltd2017-08-172017-08-29Us
Obeo Baby BubbleSoap120 mg/gTopicalC Pbio Co., Ltd2015-05-29Not applicableUs
W Lab Black Kill Pore CleanerGel.4 g/20mLTopicalWow Ventures2016-02-012017-08-30Us
International/Other Brands
Bonderlube 235 / C-Lube 10 / Dermarone / Emersol 153NF / Flexichem B / Hystrene / Industrene / Lunac / Prifac 2918 / Prodhygine
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
For SopeStearic acid (1.5 %) + Sodium lauryl sulfate (97 %)LiquidTopicalRougier Pharma Division Of Ratiopharm Inc1960-12-311999-09-27Canada
Isa Knox Ageless Serum Makeup Base 10Stearic acid (.18 mL/100mL) + Aluminum hydroxide (.18 mL/100mL) + Dimethicone (.08 mL/100mL) + Hydroxyproline (.53 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (3.38 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2010-07-04Not applicableUs
Isaknox Ageless Serum Moist Pearl BaseStearic acid (.18 mL/100mL) + Aluminum hydroxide (.18 mL/100mL) + Dimethicone (.08 mL/100mL) + Hydroxyproline (.53 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (3.38 mL/100mL)LiquidTopicalLg Household & Health Care Ltd.2010-08-31Not applicableUs
Medi Hydro DP BB CreamStearic acid (.05 mg/100mL) + Adenosine (.00004 mg/100mL) + Aluminum hydroxide (.07 mg/100mL) + Nicotinamide (.02 mg/100mL) + Titanium dioxide (.05 mg/100mL)CreamTopicalMbg Inc (Korea Institute of Science Development)2016-08-082017-08-08Us
Sha-lemStearic acid (7.25 g/30mL) + Bismuth Subcarbonate (1.89 g/30mL) + Boric acid (.95 g/30mL) + Oleic Acid (14.5 g/30mL) + Palmitic Acid (7.25 g/30mL)OintmentTopicalShalem Products, Inc.1992-05-08Not applicableUs
Sooryehan Onbit Essence Foundation 21Stearic acid (.1 mL/100mL) + Aluminum hydroxide (.1 mL/100mL) + Hydroxyproline (.5 mL/100mL) + Octinoxate (3 mL/100mL) + Titanium dioxide (.8 mL/100mL)CreamTopicalLg Household & Health Care Ltd.2011-08-25Not applicableUs
Categories
UNII
4ELV7Z65AP
CAS number
57-11-4
Weight
Average: 284.4772
Monoisotopic: 284.271530396
Chemical Formula
C18H36O2
InChI Key
QIQXTHQIDYTFRH-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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGroup IID secretory phospholipase A2Not AvailableHuman
UPeroxisome proliferator-activated receptor alphaNot AvailableHuman
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): 4640 mg/kg [Rat]. Acute dermal toxicity (LD50): >5000 mg/kg [Rabbit].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Plasmalogen SynthesisMetabolic
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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 References
Not Available
External Links
Human Metabolome Database
HMDB00827
KEGG Drug
D00119
KEGG Compound
C01530
PubChem Compound
5281
PubChem Substance
46508522
ChemSpider
5091
BindingDB
50240485
ChEBI
28842
ChEMBL
CHEMBL46403
HET
STE
Wikipedia
Stearic_acid
PDB Entries
1e7i / 1fk4 / 1hmt / 1k4w / 1lif / 1uvc / 1xxs / 2fva / 2wh5 / 2zyi
show 21 more
MSDS
Download (73.6 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CreamTopical16 g/100mL
CreamTopical15 g/10mL
CreamTopical20 g/100mL
CreamTopical8 g/100mL
CreamTopical25 g/100mL
CreamTopical
LiquidTopical
SoapTopical120 mg/g
SoapTopical12 g/100g
CreamTopical1 g/100mL
OintmentTopical
GelTopical.4 g/20mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)68.8 °CPhysProp
boiling point (°C)383 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.8808
CYP450 2D6 inhibitorNon-inhibitor0.9554
CYP450 2C19 inhibitorNon-inhibitor0.9578
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-0159-1900000000-9cc966384906cd35537d
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0159-0900000000-b87a9955374d11966ba6
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-0100-9700000000-979da356343fa0697993
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0159-2901000000-16194c704b7abd193647
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-06yo-9110000000-6f345827577cdc861aca
GC-MS Spectrum - EI-BGC-MSsplash10-075c-9220000000-207b53a511763954eb66
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-1900000000-9cc966384906cd35537d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0159-0900000000-b87a9955374d11966ba6
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0100-9700000000-979da356343fa0697993
GC-MS Spectrum - GC-MSGC-MSsplash10-0159-2901000000-16194c704b7abd193647
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-1900000000-d34fc01a79cc27a32080
Mass Spectrum (Electron Ionization)MSsplash10-0c03-9200000000-5dd52f837d56d80fa968
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-001i-0090000000-1368043827a20e28c172
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-001i-0090000000-5c3fa1d38cf3d0a38d74
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0090000000-34a309d09cb2def46a19
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-4690000000-f68e827f7ebccd80d5bf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-8920000000-2e865f09d760af582c07
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0090000000-34a309d09cb2def46a19
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-4690000000-f68e827f7ebccd80d5bf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-8920000000-2e865f09d760af582c07
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-b3ce35f839a30b41c718
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00m0-1090000000-bbb339a3dbe1b9ba0d54
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9240000000-1b84b49819fa37fce1ae
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-b3ce35f839a30b41c718
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00m0-1090000000-bbb339a3dbe1b9ba0d54
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9240000000-1b84b49819fa37fce1ae
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-00lr-0090000000-a702a9f469dbb513856a
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-9441e6362046ae198384
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-fbf3f8e91badb0ec251d
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-001i-0090000000-55efcdc9c7bfd521ef5a
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Long-chain fatty acids
Alternative Parents
Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Long-chain fatty acid / Straight chain fatty acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
long-chain fatty acid, saturated fatty acid, straight-chain saturated fatty acid (CHEBI:28842) / Straight chain fatty acids, Saturated fatty acids (C01530) / Straight chain fatty acids (LMFA01010018)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other...
Gene Name
PLA2G2D
Uniprot ID
Q9UNK4
Uniprot Name
Group IID secretory phospholipase A2
Molecular Weight
16546.1 Da
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:17139284]
  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:17016423]
  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:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Murakami K, Ide T, Suzuki M, Mochizuki T, Kadowaki T: Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. Biochem Biophys Res Commun. 1999 Jul 14;260(3):609-13. [PubMed:10403814]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oleic acid binding
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters.
Gene Name
FABP3
Uniprot ID
P05413
Uniprot Name
Fatty acid-binding protein, heart
Molecular Weight
14857.93 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
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:17139284]
  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:17016423]
  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:5773785]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:19