Relevant Data

Food Additives Approved by WHO:

Flavouring Substances Approved by European Union:

  • Oleic acid [show]

General Information

MaintermOLEIC ACID
Doc TypeASP
CAS Reg.No.(or other ID)112-80-1
Regnum 175.105
176.180
177.1200
177.2600
173.315
182.90
172.210
172.860
182.70

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID445639
IUPAC Name(Z)-octadec-9-enoic acid
InChIInChI=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 KeyZQPPMHVWECSIRJ-KTKRTIGZSA-N
Canonical SMILESCCCCCCCCC=CCCCCCCCC(=O)O
Molecular FormulaC18H34O2
Wikipediaoctadec-9-enoic acid

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight282.468
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count15
Complexity234.0
CACTVS Substructure Key Fingerprint A A A D c f B 4 M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A G g A A C A A A C A C A g A A C C A A A A g C I A C D S C A A A A A A g A A A I C A E A A A g A A B I A A Q A A Q A A E g A A I A A O I y K C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = =
Topological Polar Surface Area37.3
Monoisotopic Mass282.256
Exact Mass282.256
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count20
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


Food Additives Biosynthesis/Degradation


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9539
Human Intestinal AbsorptionHIA+0.9945
Caco-2 PermeabilityCaco2+0.8371
P-glycoprotein SubstrateNon-substrate0.5962
P-glycoprotein InhibitorNon-inhibitor0.9487
Non-inhibitor0.8964
Renal Organic Cation TransporterNon-inhibitor0.9272
Distribution
Subcellular localizationPlasma membrane0.5465
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7643
CYP450 2D6 SubstrateNon-substrate0.8954
CYP450 3A4 SubstrateNon-substrate0.6678
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.8972
CYP450 2D6 InhibitorNon-inhibitor0.9545
CYP450 2C19 InhibitorNon-inhibitor0.9467
CYP450 3A4 InhibitorNon-inhibitor0.9295
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9349
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9133
Non-inhibitor0.9103
AMES ToxicityNon AMES toxic0.9674
CarcinogensNon-carcinogens0.6568
Fish ToxicityHigh FHMT0.9712
Tetrahymena Pyriformis ToxicityHigh TPT0.9999
Honey Bee ToxicityHigh HBT0.7123
BiodegradationReady biodegradable0.8110
Acute Oral ToxicityIV0.8289
Carcinogenicity (Three-class)Non-required0.7021

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-4.0398LogS
Caco-2 Permeability1.3956LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.3991LD50, mol/kg
Fish Toxicity1.3809pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7121pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. 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 ]
  2. 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 ]
  3. 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 ]
  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. 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 ]
  6. Jensen MD: Gender differences in regional fatty acid metabolism before and after meal ingestion. J Clin Invest. 1995 Nov;96(5):2297-303.[7593616 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. Andersen TC, Pedersen JF, Nordentoft T, Olsen O: Fat and mesenteric blood flow. Scand J Gastroenterol. 1999 Sep;34(9):894-7.[10522608 ]
  21. 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 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassFatty Acyls
SubclassFatty acids and conjugates
Intermediate Tree NodesNot available
Direct ParentLong-chain fatty acids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsLong-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
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.

From ClassyFire


Targets

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. 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. 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. 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
References
  1. 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 ]
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 ]
General Function:
Transporter activity
Specific Function:
May play a role in the transport of fatty acids. Binds various fatty acids, such as arachidonic, oleic, palmitic and linolenic acid (in vitro).
Uniprot ID:
P29498
Molecular Weight:
14847.73 Da
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) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da

From T3DB