Linolenic Acid
| Internal ID | b6a12fcf-a40a-4ca3-961e-3cd0f3093573 |
| Taxonomy | Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives |
| IUPAC Name | (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid |
| SMILES (Canonical) | CCC=CCC=CCC=CCCCCCCCC(=O)O |
| SMILES (Isomeric) | CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O |
| InChI | InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9- |
| InChI Key | DTOSIQBPPRVQHS-PDBXOOCHSA-N |
| Popularity | 18,109 references in papers |
| Molecular Formula | C18H30O2 |
| Molecular Weight | 278.40 g/mol |
| Exact Mass | 278.224580195 g/mol |
| Topological Polar Surface Area (TPSA) | 37.30 Ų |
| XlogP | 5.90 |
| Atomic LogP (AlogP) | 5.66 |
| H-Bond Acceptor | 1 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 13 |
| alpha-Linolenic acid |
| 463-40-1 |
| linolenate |
| (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid |
| a-Linolenic acid |
| cis,cis,cis-9,12,15-Octadecatrienoic acid |
| all-cis-9,12,15-Octadecatrienoic acid |
| (Z,Z,Z)-9,12,15-Octadecatrienoic acid |
| 9-cis,12-cis,15-cis-Octadecatrienoic acid |
| alpha-Lnn |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9923 | 99.23% |
| Caco-2 | + | 0.6071 | 60.71% |
| Blood Brain Barrier | + | 0.8000 | 80.00% |
| Human oral bioavailability | - | 0.5714 | 57.14% |
| Subcellular localzation | Plasma membrane | 0.5044 | 50.44% |
| OATP2B1 inhibitior | - | 0.8530 | 85.30% |
| OATP1B1 inhibitior | - | 0.4580 | 45.80% |
| OATP1B3 inhibitior | - | 0.3406 | 34.06% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | + | 0.5594 | 55.94% |
| P-glycoprotein inhibitior | - | 0.8342 | 83.42% |
| P-glycoprotein substrate | - | 0.9574 | 95.74% |
| CYP3A4 substrate | - | 0.6597 | 65.97% |
| CYP2C9 substrate | + | 0.6276 | 62.76% |
| CYP2D6 substrate | - | 0.8766 | 87.66% |
| CYP3A4 inhibition | - | 0.9465 | 94.65% |
| CYP2C9 inhibition | - | 0.8798 | 87.98% |
| CYP2C19 inhibition | - | 0.9638 | 96.38% |
| CYP2D6 inhibition | - | 0.9631 | 96.31% |
| CYP1A2 inhibition | + | 0.6915 | 69.15% |
| CYP2C8 inhibition | - | 0.9243 | 92.43% |
| CYP inhibitory promiscuity | - | 0.9426 | 94.26% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.6935 | 69.35% |
| Carcinogenicity (trinary) | Non-required | 0.6373 | 63.73% |
| Eye corrosion | + | 0.9371 | 93.71% |
| Eye irritation | + | 0.8357 | 83.57% |
| Skin irritation | + | 0.7676 | 76.76% |
| Skin corrosion | - | 0.6260 | 62.60% |
| Ames mutagenesis | - | 0.8800 | 88.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.3603 | 36.03% |
| Micronuclear | - | 0.9900 | 99.00% |
| Hepatotoxicity | - | 0.6125 | 61.25% |
| skin sensitisation | + | 0.8470 | 84.70% |
| Respiratory toxicity | + | 0.7444 | 74.44% |
| Reproductive toxicity | - | 0.6531 | 65.31% |
| Mitochondrial toxicity | + | 0.7875 | 78.75% |
| Nephrotoxicity | - | 0.8766 | 87.66% |
| Acute Oral Toxicity (c) | IV | 0.6387 | 63.87% |
| Estrogen receptor binding | + | 0.5761 | 57.61% |
| Androgen receptor binding | - | 0.8917 | 89.17% |
| Thyroid receptor binding | + | 0.6398 | 63.98% |
| Glucocorticoid receptor binding | - | 0.7344 | 73.44% |
| Aromatase binding | - | 0.4910 | 49.10% |
| PPAR gamma | + | 0.8890 | 88.90% |
| Honey bee toxicity | - | 0.9918 | 99.18% |
| Biodegradation | + | 0.6750 | 67.50% |
| Crustacea aquatic toxicity | + | 0.5200 | 52.00% |
| Fish aquatic toxicity | + | 0.8175 | 81.75% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
28183.8 nM 28183.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
10000 nM 22387.2 nM 3548.1 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
125.9 nM 125.9 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
1778.3 nM 39810.7 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293237 | P54132 | Bloom syndrome protein |
39810.7 nM |
Potency |
via CMAUP
|
| CHEMBL4081 | P13726 | Coagulation factor III |
30000 nM |
IC50 |
PMID: 9834151
|
| CHEMBL221 | P23219 | Cyclooxygenase-1 |
4000 nM |
Ki |
PMID: 24088053
|
| CHEMBL1978 | P11511 | Cytochrome P450 19A1 |
44200 nM |
IC50 |
PMID: 16643058
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
15848.9 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL4422 | O14842 | Free fatty acid receptor 1 |
2884.03 nM 3162.28 nM 3000 nM |
EC50 EC50 EC50 |
PMID: 22519963
PMID: 26928019 PMID: 26928019 |
| CHEMBL5339 | Q5NUL3 | G-protein coupled receptor 120 |
2600 nM 3235.94 nM |
EC50 EC50 |
PMID: 19007110
PMID: 22519963 |
| CHEMBL1287622 | Q9Y468 | Lethal(3)malignant brain tumor-like protein 1 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
19952.6 nM |
Potency |
via CMAUP
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
28183.8 nM 31622.8 nM 28183.8 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL239 | Q07869 | Peroxisome proliferator-activated receptor alpha |
1200 nM 1200 nM 7.9 nM |
IC50 IC50 Kd |
DOI: 10.1007/s00044-008-9102-7
DOI: 10.1007/s00044-012-0285-6 via Super-PRED |
| CHEMBL3979 | Q03181 | Peroxisome proliferator-activated receptor delta |
16000 nM |
IC50 |
DOI: 10.1007/s00044-012-0285-6
|
| CHEMBL235 | P37231 | Peroxisome proliferator-activated receptor gamma |
6000 nM |
IC50 |
DOI: 10.1007/s00044-012-0285-6
|
| CHEMBL4426 | P04054 | Phospholipase A2 group 1B |
22300 nM |
IC50 |
via CMAUP
|
| CHEMBL3401 | O75469 | Pregnane X receptor |
2500 nM 2 nM |
EC50 EC50 |
PMID: 20966043
PMID: 20966043 |
| CHEMBL1293235 | P02545 | Prelamin-A/C |
22387.2 nM |
Potency |
via CMAUP
|
| CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
8912.5 nM 5011.9 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 | 96.97% | 99.17% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 95.31% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 94.53% | 98.95% |
| CHEMBL1781 | P11387 | DNA topoisomerase I | 90.68% | 97.00% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 89.12% | 90.17% |
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 | 5280934 |
| NPASS | NPC294548 |
| ChEMBL | CHEMBL8739 |
| LOTUS | LTS0275508 |
| wikiData | Q256502 |