Oleic Acid

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
Weight
Average: 282.4614
Monoisotopic: 282.255880332
Chemical Formula
C18H34O2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor alphaNot AvailableHumans
UPeroxisome proliferator-activated receptor deltaNot AvailableHumans
URetinoic acid receptor RXR-alphaNot AvailableHumans
UPeroxisome proliferator-activated receptor gamma
ligand
Humans
UMyelin P2 proteinNot AvailableHumans
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
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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
Not Available

Interactions

Drug Interactions
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

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Product Ingredients
IngredientUNIICASInChI Key
Calcium oleate4K5QQP44TZ142-17-6ZCZLQYAECBEUBH-CVBJKYQLSA-L
Oleate sodium399SL044HN143-19-1BCKXLBQYZLBQEK-KVVVOXFISA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Borage Oil CapsulesOleic Acid (148 mg) + Gamolenic acid (258 mg) + Linoleic acid (375 mg) + Palmitic Acid (96 mg)CapsuleOralGeneral Nutrition Canada Inc.2001-10-152009-08-05Canada flag
Flaxseed Oil CapsulesOleic Acid (165 mg) + Linoleic acid (144 mg) + Palmitic Acid (54 mg) + alpha-Linolenic acid (594 mg)CapsuleOralGeneral Nutrition Canada Inc.1998-05-272007-08-01Canada flag
Gla 130 Primrose OilOleic Acid (100 mg / cap) + Gamolenic acid (130 mg / cap) + Linoleic acid (900 mg / cap)CapsuleOralSeroyal International Inc.1996-01-312007-08-02Canada flag
Huile D'onagre Vitamin EOleic Acid (9 %) + Linoleic acid (72 %) + Palmitic Acid (7 %) + Stearic acid (1 %) + Vitamin E (15 %) + alpha-Linolenic acid (11 %)CapsuleOralLe Naturiste J.M.B. Inc.1987-12-312000-08-23Canada flag
Nuprimol CapOleic Acid (45 mg) + D-alpha-Tocopherol acetate (13.6 unit) + Gamolenic acid (45 mg) + Linoleic acid (340 mg)CapsuleOralNu Life Nutrition Ltd.1997-09-152005-03-15Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Sha-lemOleic 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)OintmentTopicalShalem Products, Inc.1992-05-08Not applicableUS flag

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
  1. 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]
  2. OLEIC ACID - National Library of Medicine HSDB Database - Toxnet [Link]
Human Metabolome Database
HMDB0000573
KEGG Drug
D02315
KEGG Compound
C01712
PubChem Compound
637517
PubChem Substance
46506835
ChemSpider
553123
BindingDB
50250904
RxNav
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
PhaseStatusPurposeConditionsCount
2CompletedPreventionColorectal Adenomatous Polyps1
1TerminatedTreatmentMultiple Sclerosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral
OintmentTopical
Suspension
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)13.4 °CPhysProp
boiling point (°C)360 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000121 mg/mLALOGPS
logP7.68ALOGPS
logP6.78Chemaxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.99Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity87.4 m3·mol-1Chemaxon
Polarizability37.64 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9945
Blood Brain Barrier+0.9539
Caco-2 permeable+0.8371
P-glycoprotein substrateNon-substrate0.5962
P-glycoprotein inhibitor INon-inhibitor0.9487
P-glycoprotein inhibitor IINon-inhibitor0.8964
Renal organic cation transporterNon-inhibitor0.9272
CYP450 2C9 substrateNon-substrate0.7643
CYP450 2D6 substrateNon-substrate0.8954
CYP450 3A4 substrateNon-substrate0.6678
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.8972
CYP450 2D6 inhibitorNon-inhibitor0.9545
CYP450 2C19 inhibitorNon-inhibitor0.9467
CYP450 3A4 inhibitorNon-inhibitor0.9295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9349
Ames testNon AMES toxic0.9674
CarcinogenicityNon-carcinogens0.6568
BiodegradationReady biodegradable0.811
Rat acute toxicity1.3991 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9133
hERG inhibition (predictor II)Non-inhibitor0.9103
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-MS (1 TMS)GC-MSsplash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0f6x-9640000000-29b5681d79890854ef2b
GC-MS Spectrum - GC-MSGC-MSsplash10-00nb-5900000000-3ba79fbe1b1b3b18c0ff
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00mk-3900000000-26468e9cc1331164ac25
Mass Spectrum (Electron Ionization)MSsplash10-052f-9100000000-350dc6d7ac541a3c5b67
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-e712519165236e43dfe0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-015a-9480000000-903782f1a1c0cfff8bc5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1090000000-1c66079b1eadcd36bf4a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0apj-9410000000-f17550b08ee2a5b40882
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06r6-9530000000-1a5d95fb40fb814bfdae
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0537-9000000000-e9763642b75960df6844
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.2052893
predicted
DarkChem Lite v0.1.0
[M-H]-207.5113893
predicted
DarkChem Lite v0.1.0
[M-H]-207.3648893
predicted
DarkChem Lite v0.1.0
[M-H]-182.34645
predicted
DeepCCS 1.0 (2019)
[M+H]+184.70445
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.79759
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights 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
  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. [Article]
  2. 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]
  3. 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
  1. 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
  1. 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
  1. 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
  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. [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
  1. 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]
  2. 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]
  3. 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]
  4. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [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
  1. 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
  1. 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]
  2. 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]
  3. 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
  1. 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]
  2. 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]
  3. 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54