Linoleic Acid
| Internal ID | 70d4a767-4a6b-4267-9fa6-267a6bbbb0ff |
| Taxonomy | Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives |
| IUPAC Name | (9Z,12Z)-octadeca-9,12-dienoic acid |
| SMILES (Canonical) | CCCCCC=CCC=CCCCCCCCC(=O)O |
| SMILES (Isomeric) | CCCCC/C=C\C/C=C\CCCCCCCC(=O)O |
| InChI | InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- |
| InChI Key | OYHQOLUKZRVURQ-HZJYTTRNSA-N |
| Popularity | 35,520 references in papers |
| Molecular Formula | C18H32O2 |
| Molecular Weight | 280.40 g/mol |
| Exact Mass | 280.240230259 g/mol |
| Topological Polar Surface Area (TPSA) | 37.30 Ų |
| XlogP | 6.80 |
| Atomic LogP (AlogP) | 5.88 |
| H-Bond Acceptor | 1 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 14 |
| 60-33-3 |
| Linolic acid |
| (9Z,12Z)-octadeca-9,12-dienoic acid |
| Telfairic acid |
| cis,cis-Linoleic acid |
| Linoleate |
| 9,12-Linoleic acid |
| Emersol 315 |
| cis,cis-9,12-Octadecadienoic acid |
| Unifac 6550 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9947 | 99.47% |
| Caco-2 | + | 0.6201 | 62.01% |
| Blood Brain Barrier | + | 0.8250 | 82.50% |
| Human oral bioavailability | - | 0.6000 | 60.00% |
| Subcellular localzation | Plasma membrane | 0.5465 | 54.65% |
| OATP2B1 inhibitior | - | 0.8511 | 85.11% |
| OATP1B1 inhibitior | - | 0.6267 | 62.67% |
| OATP1B3 inhibitior | - | 0.5698 | 56.98% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.9000 | 90.00% |
| BSEP inhibitior | - | 0.5686 | 56.86% |
| P-glycoprotein inhibitior | - | 0.8702 | 87.02% |
| P-glycoprotein substrate | - | 0.9531 | 95.31% |
| CYP3A4 substrate | - | 0.6641 | 66.41% |
| CYP2C9 substrate | + | 0.6276 | 62.76% |
| CYP2D6 substrate | - | 0.8766 | 87.66% |
| CYP3A4 inhibition | - | 0.9295 | 92.95% |
| CYP2C9 inhibition | - | 0.8972 | 89.72% |
| CYP2C19 inhibition | - | 0.9467 | 94.67% |
| CYP2D6 inhibition | - | 0.9545 | 95.45% |
| CYP1A2 inhibition | + | 0.9107 | 91.07% |
| CYP2C8 inhibition | - | 0.8932 | 89.32% |
| CYP inhibitory promiscuity | - | 0.9349 | 93.49% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.7035 | 70.35% |
| Carcinogenicity (trinary) | Non-required | 0.7021 | 70.21% |
| Eye corrosion | + | 0.9611 | 96.11% |
| Eye irritation | + | 0.9075 | 90.75% |
| Skin irritation | + | 0.8622 | 86.22% |
| Skin corrosion | + | 0.6450 | 64.50% |
| Ames mutagenesis | - | 0.9900 | 99.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4609 | 46.09% |
| Micronuclear | - | 1.0000 | 100.00% |
| Hepatotoxicity | + | 0.6125 | 61.25% |
| skin sensitisation | + | 0.8676 | 86.76% |
| Respiratory toxicity | - | 0.6222 | 62.22% |
| Reproductive toxicity | - | 0.7866 | 78.66% |
| Mitochondrial toxicity | + | 0.5625 | 56.25% |
| Nephrotoxicity | - | 0.7711 | 77.11% |
| Acute Oral Toxicity (c) | IV | 0.8289 | 82.89% |
| Estrogen receptor binding | - | 0.4798 | 47.98% |
| Androgen receptor binding | - | 0.8509 | 85.09% |
| Thyroid receptor binding | + | 0.6327 | 63.27% |
| Glucocorticoid receptor binding | - | 0.7922 | 79.22% |
| Aromatase binding | - | 0.7229 | 72.29% |
| PPAR gamma | + | 0.8956 | 89.56% |
| Honey bee toxicity | - | 0.9963 | 99.63% |
| Biodegradation | + | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | + | 0.8400 | 84.00% |
| Fish aquatic toxicity | + | 0.9649 | 96.49% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
8912.5 nM |
Potency |
via CMAUP
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
17782.8 nM |
Potency |
via CMAUP
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
158.5 nM 158.5 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL4081 | P13726 | Coagulation factor III |
41000 nM |
IC50 |
PMID: 9834151
|
| CHEMBL221 | P23219 | Cyclooxygenase-1 |
13000 nM |
IC50 |
PMID: 16038536
|
| CHEMBL1978 | P11511 | Cytochrome P450 19A1 |
48000 nM |
IC50 |
PMID: 16643058
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL2083 | P15090 | Fatty acid binding protein adipocyte |
17700 nM 13600 nM |
IC50 IC50 |
PMID: 25461324
PMID: 20471252 |
| CHEMBL3344 | P05413 | Fatty acid binding protein muscle |
1000 nM 1000 nM 1000 nM |
IC50 IC50 IC50 |
PMID: 25461324
PMID: 20471252 PMID: 25461324 |
| CHEMBL4422 | O14842 | Free fatty acid receptor 1 |
540 nM 540 nM 540 nM 549.54 nM |
EC50 EC50 EC50 EC50 |
PMID: 18993064
PMID: 18993064 via Super-PRED PMID: 18993064 |
| CHEMBL5339 | Q5NUL3 | G-protein coupled receptor 120 |
316.23 nM 316.23 nM |
EC50 EC50 |
PMID: 24881566
via Super-PRED |
| CHEMBL239 | Q07869 | Peroxisome proliferator-activated receptor alpha |
1100 nM 4.8 nM 1100 nM |
IC50 Kd IC50 |
DOI: 10.1007/s00044-012-0285-6
via Super-PRED DOI: 10.1007/s00044-008-9102-7 |
| CHEMBL3979 | Q03181 | Peroxisome proliferator-activated receptor delta |
10000 nM |
IC50 |
DOI: 10.1007/s00044-012-0285-6
|
| CHEMBL235 | P37231 | Peroxisome proliferator-activated receptor gamma |
6200 nM |
IC50 |
DOI: 10.1007/s00044-012-0285-6
|
| CHEMBL1293235 | P02545 | Prelamin-A/C |
177.8 nM 177.8 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 98.02% | 99.17% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.79% | 98.95% |
| CHEMBL4769 | O95749 | Geranylgeranyl pyrophosphate synthetase | 95.05% | 92.08% |
| CHEMBL230 | P35354 | Cyclooxygenase-2 | 94.84% | 89.63% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 94.03% | 96.09% |
| CHEMBL1781 | P11387 | DNA topoisomerase I | 92.92% | 97.00% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 90.48% | 90.17% |
| CHEMBL2265 | P23141 | Acyl coenzyme A:cholesterol acyltransferase | 88.44% | 85.94% |
| CHEMBL3359 | P21462 | Formyl peptide receptor 1 | 82.54% | 93.56% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 81.76% | 96.95% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
To see more specific details click the taxa you are interested in.
To see more specific details click the taxa you are interested in.
| PubChem | 5280450 |
| NPASS | NPC85813 |
| ChEMBL | CHEMBL267476 |
| LOTUS | LTS0013198 |
| wikiData | Q407426 |