Tmic
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Record Information
Version2.0
Creation Date2014-09-11 05:17:15 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4802
Identification
Common NameOleic acid
ClassSmall Molecule
DescriptionOleic acid is an unsaturated fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colourless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid. Oleic acid 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. Oleic acid is a major constituent of plant oils e.g. olive oil (about 80%), almond oil (about 80%) and many others, mainly as glyceride. It is also a constituent of tall oil and present in fruits. Oleic acid is a food additive and is used in manufacturing of surfactants, soaps, plasticizers. It is also an emulsifying agent in foods and pharmaceuticals. Oleic acid is a known skin penetrant and may also be used as an herbicide, insecticide, and fungicide.
Compound Type
  • Animal Toxin
  • Food Additive
  • Food Toxin
  • Fungicide
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pesticide
  • Plant Toxin
  • Plasticizer
  • Solvent
Chemical Structure
Thumb
Synonyms
Synonym
(9Z)-9-Octadecenoate
(9Z)-9-Octadecenoic acid
(9Z)-Octadecenoate
(9Z)-Octadecenoic acid
(Z)-9-Octadecanoate
(Z)-9-Octadecanoic acid
(Z)-Octadec-9-enoate
(Z)-Octadec-9-enoic acid
9,10-Octadecenoate
9,10-Octadecenoic acid
9-(Z)-Octadecenoate
9-(Z)-Octadecenoic acid
9-Octadecenoate
9-Octadecenoic acid
Century cd fatty acid
cis-9-Octadecenoate
cis-9-Octadecenoic acid
cis-Octadec-9-enoate
cis-Octadec-9-enoic acid
cis-Oleate
cis-Oleic acid
Distoline
Emersol 210
Emersol 211
Emersol 213
Emersol 220 White Oleate
Emersol 220 White Oleic acid
Emersol 221 Low Titer White Oleate
Emersol 221 Low Titer White Oleic acid
Emersol 233ll
Emersol 6321
Emersol 6333 NF
Emersol 7021
Glycon ro
Glycon wo
Groco 2
Groco 4
Groco 5L
Groco 6
Industrene 104
Industrene 105
Industrene 205
Industrene 206
L'acide oleique
Metaupon
Oelsauere
Oleate
Oleic acid extra pure
Oleinate
Oleinic acid
Pamolyn
Pamolyn 100
Pamolyn 100 FG
Pamolyn 100 FGK
Pamolyn 125
Priolene 6900
Red oil
Tego-oleic 130
Vopcolene 27
Wecoline OO
Z-9-Octadecenoate
Z-9-Octadecenoic acid
Chemical FormulaC18H34O2
Average Molecular Mass282.461 g/mol
Monoisotopic Mass282.256 g/mol
CAS Registry Number112-80-1
IUPAC Name(9Z)-octadec-9-enoic acid
Traditional Nameoleic acid
SMILES[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(O)=O
InChI IdentifierInChI=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-
InChI KeyInChIKey=ZQPPMHVWECSIRJ-KTKRTIGZSA-N
Chemical Taxonomy
Description 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
  • Unsaturated 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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Intestine
  • Liver
  • Muscle
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Skin
  • Stratum Corneum
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point13.4°C
Boiling Point360°C
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-00vi-9500000000-cdb5366d3ece43c3e166View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-fc03835c9c8fddb27970View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9100000000-7618883a87bd14687fd5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00vi-9500000000-cdb5366d3ece43c3e166View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00nb-5900000000-fc03835c9c8fddb27970View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-9640000000-29b5681d79890854ef2bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fe0-9431000000-1879934642ac672cb401View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ls-4790000000-d753b2905852ca2a8cbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aou-9000000000-64594906d693e8a08650View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-00l2-4790000000-aefa66e9f83fcb24ead6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0apm-9100000000-a71c58b95cb65487eeedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0aou-9000000000-5889cbe3dd606123df50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negativesplash10-001i-0090000000-89531b488fbe899c09e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-052f-9100000000-de078efada08e691dbb8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac359View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0090000000-92096c6b229762c5295fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-5fe8495a19b387bf702cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-5d40399b1c736b476445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0090000000-45785aeb659bd8a09240View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-001i-0091000000-3946ac7663105c7c2700View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-001i-0090000000-ce1372cb3b5e84122349View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0090000000-92096c6b229762c5295fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0090000000-755e8d1537818580a2fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00y0-4690000000-ca39c5846217fe093227View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9830000000-fcb2923d448d11c54559View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-e809fd7222cf63431b77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1090000000-9c340e3d19cbe7013ccdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9230000000-6e517cda629fcd4df07dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9100000000-350dc6d7ac541a3c5b67View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB04224
HMDB IDHMDB00207
PubChem Compound ID445639
ChEMBL IDCHEMBL8659
ChemSpider ID393217
KEGG IDC00712
UniProt IDNot Available
OMIM ID
ChEBI ID16196
BioCyc IDOLEATE-CPD
CTD IDD019301
Stitch IDNot Available
PDB IDOLA
ACToR IDNot Available
Wikipedia LinkOleic acid
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.

MSDSLink
General References
  1. Takahashi K, Rytting JH: Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. J Pharm Pharmacol. 2001 Jun;53(6):789-94. [11428654 ]
  2. Jensen MD: Gender differences in regional fatty acid metabolism before and after meal ingestion. J Clin Invest. 1995 Nov;96(5):2297-303. [7593616 ]
  3. Russell AP, Somm E, Debigare R, Hartley O, Richard D, Gastaldi G, Melotti A, Michaud A, Giacobino JP, Muzzin P, LeBlanc P, Maltais F: COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers. J Cardiopulm Rehabil. 2004 Sep-Oct;24(5):332-9. [15602154 ]
  4. Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [10391868 ]
  5. Colette C, Percheron C, Pares-Herbute N, Michel F, Pham TC, Brillant L, Descomps B, Monnier L: Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors. Int J Obes Relat Metab Disord. 2003 Jun;27(6):648-56. [12833107 ]
  6. Christophe AB, De Greyt WF, Delanghe JR, Huyghebaert AD: Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man. Ann Nutr Metab. 2000;44(2):61-7. [10970994 ]
  7. de la Maza MP, Hirsch S, Nieto S, Petermann M, Bunout D: Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage. Alcohol Clin Exp Res. 1996 Nov;20(8):1418-22. [8947319 ]
  8. Droke EA, Briske-Anderson M, Lukaski HC: Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells. Biol Trace Elem Res. 2003 Dec;95(3):219-32. [14665727 ]
  9. Valjakka-Koskela R, Hirvonen J, Monkkonen J, Kiesvaara J, Antila S, Lehtonen L, Urtti A: Transdermal delivery of levosimendan. Eur J Pharm Sci. 2000 Oct;11(4):343-50. [11033078 ]
  10. Jones AE, Stolinski M, Smith RD, Murphy JL, Wootton SA: Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women. Br J Nutr. 1999 Jan;81(1):37-43. [10341674 ]
  11. Thielitz A, Helmdach M, Ropke EM, Gollnick H: Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. Br J Dermatol. 2001 Jul;145(1):19-27. [11453902 ]
  12. Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30. [7929039 ]
  13. Lima WP, Carnevali LC Jr, Eder R, Costa Rosa LF, Bacchi EM, Seelaender MC: Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. Clin Nutr. 2005 Dec;24(6):1019-28. Epub 2005 Sep 22. [16182414 ]
  14. Vinggaard AM, Provost JJ, Exton JH, Hansen HS: Arf and RhoA regulate both the cytosolic and the membrane-bound phospholipase D from human placenta. Cell Signal. 1997 Feb;9(2):189-96. [9113419 ]
  15. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [8412012 ]
  16. Mittendorfer B, Liem O, Patterson BW, Miles JM, Klein S: What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean? Diabetes. 2003 Jul;52(7):1641-8. [12829627 ]
  17. Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [11124748 ]
  18. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [16249438 ]
  19. Andersen TC, Pedersen JF, Nordentoft T, Olsen O: Fat and mesenteric blood flow. Scand J Gastroenterol. 1999 Sep;34(9):894-7. [10522608 ]
  20. Ayala-Bravo HA, Quintanar-Guerrero D, Naik A, Kalia YN, Cornejo-Bravo JM, Ganem-Quintanar A: Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability. Pharm Res. 2003 Aug;20(8):1267-73. [12948025 ]
  21. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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 oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC508.87 uMNVS_NR_hPPARaNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
  2. 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. [10403814 ]
  3. 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. [15491415 ]
  4. 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. [16731579 ]
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
Molecular Weight:
14909.305 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. [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. [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. [10592235 ]
General Function:
Lipid binding
Specific Function:
Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides.
Gene Name:
GLTP
Uniprot ID:
Q9NZD2
Molecular Weight:
23849.6 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. [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. [17016423 ]
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-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand.
Gene Name:
PPARD
Uniprot ID:
Q03181
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. [16731579 ]
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 expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXRs is 9-cis retinoic acid. RXRA serves as a common heterodimeric partner for a number of nuclear receptors. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. The RXRA/PPARA heterodimer is required for PPARA transcriptional activity on fatty acid oxidation genes such as ACOX1 and the P450 system genes.
Gene Name:
RXRA
Uniprot ID:
P19793
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. [16731579 ]