Identification
- Summary
Oleic Acid is a naturally occurring fatty acid with antibacterial properties added to a variety of drug products.
- Generic Name
- Oleic Acid
- DrugBank Accession Number
- DB04224
- Background
An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed)
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Oleic Acid (DB04224)
- Weight
- Average: 282.4614
Monoisotopic: 282.255880332 - Chemical Formula
- C18H34O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPeroxisome proliferator-activated receptor alpha Not Available Humans UPeroxisome proliferator-activated receptor delta Not Available Humans URetinoic acid receptor RXR-alpha Not Available Humans UPeroxisome proliferator-activated receptor gamma ligandHumans UMyelin P2 protein Not Available Humans - Absorption
Fatty acid uptake by different tissues may be mediated via passive diffusion to facilitated diffusion or a combination of both 2. Fatty acids taken up by tissues are then stored in the form of triglycerides or oxidized 2. Oleic acid was shown to penetrate rat skin 2. Following oral administration of Brucea javanica oil emulsion in rats, the time of oleic acid to reach peak plasma concentration was approximately 15.6 hours 1.
- Volume of distribution
Radio-labelled oleic acid was detected in the heart, liver, lung, spleen, kidney, muscle, intestine, adrenal, blood, and lymph, and adipose, mucosal, and dental tissues 2. Oleic acid is primarily transported via the lymphatic system 2.
- Protein binding
As with other fatty acids originating from adipose tissue stores, oleic acid may bind to serum albumin or remain unesterified in the blood 2.
- Metabolism
Like most fatty acids, oleic acid may undergo oxidation via beta-oxidation and tricarboxylic acid cycle pathways of catabolism, where an additional isomerization reaction is required for the complete catabolism of oleic acid. Via a series of elongation and desaturation steps, oleic acid may be converted into longer chain eicosatrienoic and nervonic acid 2.
- Route of elimination
Following oral administration of trace amounts of oleic acid, less than 10% of total oleic acid was found to be eliminated via fecal excretion 2.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
In rat, oral LD50 74 g/kg and intravenous LD50 is 2.4 mg/kg 2. Dermal LD50 in guinea pig was >3000 mg/kg 2.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Calcium oleate 4K5QQP44TZ 142-17-6 ZCZLQYAECBEUBH-CVBJKYQLSA-L Oleate sodium 399SL044HN 143-19-1 BCKXLBQYZLBQEK-KVVVOXFISA-M - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Borage Oil Capsules Oleic Acid (148 mg) + Gamolenic acid (258 mg) + Linoleic acid (375 mg) + Palmitic Acid (96 mg) Capsule Oral General Nutrition Canada Inc. 2001-10-15 2009-08-05 Canada 
Flaxseed Oil Capsules Oleic Acid (165 mg) + Linoleic acid (144 mg) + Palmitic Acid (54 mg) + alpha-Linolenic acid (594 mg) Capsule Oral General Nutrition Canada Inc. 1998-05-27 2007-08-01 Canada Gla 130 Primrose Oil Oleic Acid (100 mg / cap) + Gamolenic acid (130 mg / cap) + Linoleic acid (900 mg / cap) Capsule Oral Seroyal International Inc. 1996-01-31 2007-08-02 Canada Huile D'onagre Vitamin E Oleic Acid (9 %) + Linoleic acid (72 %) + Palmitic Acid (7 %) + Stearic acid (1 %) + Vitamin E (15 %) + alpha-Linolenic acid (11 %) Capsule Oral Le Naturiste J.M.B. Inc. 1987-12-31 2000-08-23 Canada Nuprimol Cap Oleic Acid (45 mg) + D-alpha-Tocopherol acetate (13.6 unit) + Gamolenic acid (45 mg) + Linoleic acid (340 mg) Capsule Oral Nu Life Nutrition Ltd. 1997-09-15 2005-03-15 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Sha-lem Oleic Acid (14.5 g/30mL) + Bismuth subcarbonate (1.89 g/30mL) + Boric acid (0.95 g/30mL) + Palmitic Acid (7.25 g/30mL) + Stearic acid (7.25 g/30mL) Ointment Topical Shalem Products, Inc. 1992-05-08 Not applicable US 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Unsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Long-chain fatty acid / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- octadec-9-enoic acid (CHEBI:27997) / Unsaturated fatty acids, Monounsaturated fatty acids (C01712) / Unsaturated fatty acids (LMFA01030073)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4837010H8C
- CAS number
- 112-80-1
- InChI Key
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N
- InChI
- InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
- IUPAC Name
- (9E)-octadec-9-enoic acid
- SMILES
- CCCCCCCC\C=C\CCCCCCCC(O)=O
References
- Synthesis Reference
Ansgar Behler, Hermann Anzinger, Michael Vogt, "Process for the preparation of light-colored oleic acid sulfonates." U.S. Patent US5294726, issued June, 1972.
US5294726- General References
- Su H, Zhang Y, Huang W, Wen L, Zhuang Z, Chen G: Pharmacokinetics and Tissue Distribution of Oleic and Linoleic Acids Following Oral and Rectal Administration of Brucea javanica Oil in Rats International Journal of Pharmacology. 2016 January 1;12(5):461-482. [Article]
- OLEIC ACID - National Library of Medicine HSDB Database - Toxnet [Link]
- External Links
- Human Metabolome Database
- HMDB0000573
- KEGG Drug
- D02315
- KEGG Compound
- C01712
- PubChem Compound
- 637517
- PubChem Substance
- 46506835
- ChemSpider
- 553123
- BindingDB
- 50250904
- 7631
- ChEBI
- 27997
- ChEMBL
- CHEMBL460657
- ZINC
- ZINC000008217338
- PDBe Ligand
- ELA
- Wikipedia
- Oleic_acid
- PDB Entries
- 1hmr / 3lup / 4jiv / 4jj2 / 4ku0 / 4osd / 6p1z / 6p20 / 6p22 / 6p2a … show 3 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Prevention Colorectal Adenomatous Polyps 1 1 Terminated Treatment Multiple Sclerosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Ointment Topical Suspension - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 13.4 °C PhysProp boiling point (°C) 360 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.000121 mg/mL ALOGPS logP 7.68 ALOGPS logP 6.78 Chemaxon logS -6.4 ALOGPS pKa (Strongest Acidic) 4.99 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 15 Chemaxon Refractivity 87.4 m3·mol-1 Chemaxon Polarizability 37.64 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9945 Blood Brain Barrier + 0.9539 Caco-2 permeable + 0.8371 P-glycoprotein substrate Non-substrate 0.5962 P-glycoprotein inhibitor I Non-inhibitor 0.9487 P-glycoprotein inhibitor II Non-inhibitor 0.8964 Renal organic cation transporter Non-inhibitor 0.9272 CYP450 2C9 substrate Non-substrate 0.7643 CYP450 2D6 substrate Non-substrate 0.8954 CYP450 3A4 substrate Non-substrate 0.6678 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.8972 CYP450 2D6 inhibitor Non-inhibitor 0.9545 CYP450 2C19 inhibitor Non-inhibitor 0.9467 CYP450 3A4 inhibitor Non-inhibitor 0.9295 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9349 Ames test Non AMES toxic 0.9674 Carcinogenicity Non-carcinogens 0.6568 Biodegradation Ready biodegradable 0.811 Rat acute toxicity 1.3991 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9133 hERG inhibition (predictor II) Non-inhibitor 0.9103
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 207.2052893 predictedDarkChem Lite v0.1.0 [M-H]- 207.5113893 predictedDarkChem Lite v0.1.0 [M-H]- 207.3648893 predictedDarkChem Lite v0.1.0 [M-H]- 182.34645 predictedDeepCCS 1.0 (2019) [M+H]+ 184.70445 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.79759 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Downie MM, Sanders DA, Maier LM, Stock DM, Kealey T: Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. Br J Dermatol. 2004 Oct;151(4):766-75. [Article]
- Vanden Heuvel JP, Thompson JT, Frame SR, Gillies PJ: Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci. 2006 Aug;92(2):476-89. Epub 2006 May 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-lin...
- Gene Name
- PPARD
- Uniprot ID
- Q03181
- Uniprot Name
- Peroxisome proliferator-activated receptor delta
- Molecular Weight
- 49902.99 Da
References
- Vanden Heuvel JP, Thompson JT, Frame SR, Gillies PJ: Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci. 2006 Aug;92(2):476-89. Epub 2006 May 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 Da
References
- Vanden Heuvel JP, Thompson JT, Frame SR, Gillies PJ: Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci. 2006 Aug;92(2):476-89. Epub 2006 May 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Ligand
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 Da
References
- Zhang L, Ren XM, Wan B, Guo LH: Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor gamma. Toxicol Appl Pharmacol. 2014 Sep 15;279(3):275-83. doi: 10.1016/j.taap.2014.06.020. Epub 2014 Jul 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transporter activity
- Specific Function
- May play a role in lipid transport protein in Schwann cells. May bind cholesterol.
- Gene Name
- PMP2
- Uniprot ID
- P02689
- Uniprot Name
- Myelin P2 protein
- Molecular Weight
- 14909.305 Da
References
- 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. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- 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
- Veerkamp JH, van Moerkerk HT, Prinsen CF, van Kuppevelt TH: Structural and functional studies on different human FABP types. Mol Cell Biochem. 1999 Feb;192(1-2):137-42. [Article]
- Unterberg C, Heidl G, von Bassewitz DB, Spener F: Isolation and characterization of the fatty acid binding protein from human heart. J Lipid Res. 1986 Dec;27(12):1287-93. [Article]
- Paulussen RJ, van der Logt CP, Veerkamp JH: Characterization and binding properties of fatty acid-binding proteins from human, pig, and rat heart. Arch Biochem Biophys. 1988 Aug 1;264(2):533-45. doi: 10.1016/0003-9861(88)90319-0. [Article]
- Said B, Schulz H: Fatty acid binding protein from rat heart. The fatty acid binding proteins from rat heart and liver are different proteins. J Biol Chem. 1984 Jan 25;259(2):1155-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Phospholipid binding
- Specific Function
- Plays a role in lipoprotein-mediated cholesterol uptake in hepatocytes (PubMed:25732850). Binds cholesterol (PubMed:25732850). Binds free fatty acids and their coenzyme A derivatives, bilirubin, an...
- Gene Name
- FABP1
- Uniprot ID
- P07148
- Uniprot Name
- Fatty acid-binding protein, liver
- Molecular Weight
- 14208.34 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Petitpas I, Grune T, Bhattacharya AA, Curry S: Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. J Mol Biol. 2001 Dec 14;314(5):955-60. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vitamin transporter activity
- Specific Function
- Involved in vitamin D transport and storage, scavenging of extracellular G-actin, enhancement of the chemotactic activity of C5 alpha for neutrophils in inflammation and macrophage activation.
- Gene Name
- GC
- Uniprot ID
- P02774
- Uniprot Name
- Vitamin D-binding protein
- Molecular Weight
- 52963.025 Da
References
- Ena JM, Esteban C, Perez MD, Uriel J, Calvo M: Fatty acids bound to vitamin D-binding protein (DBP) from human and bovine sera. Biochem Int. 1989 Jul;19(1):1-7. [Article]
- Morucci G, Branca JJ, Gulisano M, Ruggiero M, Paternostro F, Pacini A, Di Cesare Mannelli L, Pacini S: Gc-protein-derived macrophage activating factor counteracts the neuronal damage induced by oxaliplatin. Anticancer Drugs. 2015 Feb;26(2):197-209. doi: 10.1097/CAD.0000000000000177. [Article]
- Ruggiero M, Ward E, Smith R, Branca JJ, Noakes D, Morucci G, Taubmann M, Thyer L, Pacini S: Oleic Acid, deglycosylated vitamin D-binding protein, nitric oxide: a molecular triad made lethal to cancer. Anticancer Res. 2014 Jul;34(7):3569-78. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transporter activity
- Specific Function
- B-FABP could be involved in the transport of a so far unknown hydrophobic ligand with potential morphogenic activity during CNS development. It is required for the establishment of the radial glial...
- Gene Name
- FABP7
- Uniprot ID
- O15540
- Uniprot Name
- Fatty acid-binding protein, brain
- Molecular Weight
- 14888.855 Da
References
- Balendiran GK, Schnutgen F, Scapin G, Borchers T, Xhong N, Lim K, Godbout R, Spener F, Sacchettini JC: Crystal structure and thermodynamic analysis of human brain fatty acid-binding protein. J Biol Chem. 2000 Sep 1;275(35):27045-54. [Article]
- Xu LZ, Sanchez R, Sali A, Heintz N: Ligand specificity of brain lipid-binding protein. J Biol Chem. 1996 Oct 4;271(40):24711-9. doi: 10.1074/jbc.271.40.24711. [Article]
- Veerkamp JH, van Moerkerk HT, Prinsen CF, van Kuppevelt TH: Structural and functional studies on different human FABP types. Mol Cell Biochem. 1999 Feb;192(1-2):137-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transporter activity
- Specific Function
- Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
- Gene Name
- FABP4
- Uniprot ID
- P15090
- Uniprot Name
- Fatty acid-binding protein, adipocyte
- Molecular Weight
- 14718.815 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54