OLEIC ACID
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
Mainterm | OLEIC ACID |
Doc Type | ASP |
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 SDF2D Structure | |
CID | 445639 |
IUPAC Name | (Z)-octadec-9-enoic acid |
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- |
InChI Key | ZQPPMHVWECSIRJ-KTKRTIGZSA-N |
Canonical SMILES | CCCCCCCCC=CCCCCCCCC(=O)O |
Molecular Formula | C18H34O2 |
Wikipedia | octadec-9-enoic acid |
From Pubchem
Computed Properties
Property Name | Property Value |
---|---|
Molecular Weight | 282.468 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 15 |
Complexity | 234.0 |
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 Area | 37.3 |
Monoisotopic Mass | 282.256 |
Exact Mass | 282.256 |
Compound Is Canonicalized | True |
Formal Charge | 0 |
Heavy Atom Count | 20 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 1 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9539 |
Human Intestinal Absorption | HIA+ | 0.9945 |
Caco-2 Permeability | Caco2+ | 0.8371 |
P-glycoprotein Substrate | Non-substrate | 0.5962 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9487 |
Non-inhibitor | 0.8964 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9272 |
Distribution | ||
Subcellular localization | Plasma membrane | 0.5465 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7643 |
CYP450 2D6 Substrate | Non-substrate | 0.8954 |
CYP450 3A4 Substrate | Non-substrate | 0.6678 |
CYP450 1A2 Inhibitor | 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 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9349 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9133 |
Non-inhibitor | 0.9103 | |
AMES Toxicity | Non AMES toxic | 0.9674 |
Carcinogens | Non-carcinogens | 0.6568 |
Fish Toxicity | High FHMT | 0.9712 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9999 |
Honey Bee Toxicity | High HBT | 0.7123 |
Biodegradation | Ready biodegradable | 0.8110 |
Acute Oral Toxicity | IV | 0.8289 |
Carcinogenicity (Three-class) | Non-required | 0.7021 |
From admetSAR
ADMET Predicted Profile --- Regression
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -4.0398 | LogS |
Caco-2 Permeability | 1.3956 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.3991 | LD50, mol/kg |
Fish Toxicity | 1.3809 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.7121 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
Route of Exposure | None |
---|---|
Mechanism of Toxicity | None |
Metabolism | None |
Toxicity Values | None |
Lethal Dose | None |
Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
Minimum Risk Level | None |
Health Effects | None |
Treatment | None |
Reference |
|
From T3DB
Taxonomic Classification
Kingdom | Organic compounds |
---|---|
Superclass | Lipids and lipid-like molecules |
Class | Fatty Acyls |
Subclass | Fatty acids and conjugates |
Intermediate Tree Nodes | Not available |
Direct Parent | Long-chain fatty acids |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
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 |
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. |
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
- 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
- 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
- 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
- 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
- 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