Ethyl linolenate

Details

• Internal ID: fafcd76f-0489-42c2-b100-a3843c8a99b3
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
• IUPAC Name: ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• SMILES (Canonical): CCC=CCC=CCC=CCCCCCCCC(=O)OCC
• SMILES (Isomeric): CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)OCC
• InChI: InChI=1S/C20H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h5-6,8-9,11-12H,3-4,7,10,13-19H2,1-2H3/b6-5-,9-8-,12-11-
• InChI Key: JYYFMIOPGOFNPK-AGRJPVHOSA-N
• Popularity: 247 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.50 g/mol
• Exact Mass: 306.255880323 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 6.14
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 14

Synonyms

• 1191-41-9
• Linolenic acid ethyl ester
• Linolenic acid, ethyl ester
• (9Z,12Z,15Z)-Ethyl octadeca-9,12,15-trienoate
• ethyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
• Ethyl (Z,Z,Z)-9,12,15-octadecatrienoate
• ethyl alpha-linolenate
• 9,12,15-Octadecatrienoic acid, ethyl ester, (Z,Z,Z)-
• EINECS 214-734-6
• 9,12,15-Octadecatrienoic acid, ethyl ester, (9Z,12Z,15Z)-
• NSC 607760
• Ethyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
• UNII-T54Y8H042V
• DTXSID6025307
• CHEBI:84851
• T54Y8H042V
• Ethyl (9E,12E,15E)-octadeca-9,12,15-trienoate
• NSC-607760
• 9,12,15-Octadecatrienoic acid, ethyl ester
• NSC607760
• Ethyl 9.alpha.-linolenate
• Ethyl linolenate, >=98%
• SCHEMBL122342
• ETHYL LINOLENATE [INCI]
• CHEMBL2005772
• ETHYL LINOLENATE [WHO-DD]
• JYYFMIOPGOFNPK-AGRJPVHOSA-N
• DTXCID801333886
• Ethyl 9,12,15-octadecatrienoate
• HMS3650O11
• LS-90
• HY-N2073
• Tox21_201013
• MFCD07371452
• AKOS016010181
• 1-(3-Chloropiperazin-2-yl)methanamine
• ethyl (9Z,12Z,15Z)-octadecatrienoate
• NCGC00258566-01
• AC-33779
• AS-70359
• CAS-1191-41-9
• CS-0018578
• Ethyl cis,cis,cis-9,12,15-octadecatrienoate
• A892646
• SR-01000946818
• (9Z,12Z,15Z)ethyl octadeca-9,12,15-trienoate
• J-004074
• J-803006
• SR-01000946818-1
• Q27158118
• cis,cis,cis-octadeca-9,12,15-trienoic acid ethyl ester
• (Z,Z,Z)-9,12,15-OCTADECATRIENOIC ACID ETHYL ESTER
• Ethyl (9Z, 12Z, 15Z)- 9, 12, 15- octadecatrienoate
• ETHYL ESTER 9,12,15-OCTADECATRIENOIC ACID (ZZZ)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9966	99.66%
Caco-2	+	0.7371	73.71%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4494	44.94%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.7664	76.64%
OATP1B3 inhibitior	+	0.9307	93.07%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8355	83.55%
P-glycoprotein inhibitior	-	0.6533	65.33%
P-glycoprotein substrate	-	0.9676	96.76%
CYP3A4 substrate	-	0.5256	52.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9476	94.76%
CYP2C9 inhibition	-	0.9392	93.92%
CYP2C19 inhibition	-	0.9562	95.62%
CYP2D6 inhibition	-	0.9277	92.77%
CYP1A2 inhibition	-	0.5469	54.69%
CYP2C8 inhibition	-	0.8399	83.99%
CYP inhibitory promiscuity	-	0.6856	68.56%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6000	60.00%
Carcinogenicity (trinary)	Non-required	0.6347	63.47%
Eye corrosion	+	0.9652	96.52%
Eye irritation	+	0.6077	60.77%
Skin irritation	-	0.6340	63.40%
Skin corrosion	-	0.9971	99.71%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8275	82.75%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.6013	60.13%
skin sensitisation	+	0.8385	83.85%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	-	0.9889	98.89%
Mitochondrial toxicity	-	0.9750	97.50%
Nephrotoxicity	-	0.7859	78.59%
Acute Oral Toxicity (c)	III	0.7762	77.62%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.9227	92.27%
Thyroid receptor binding	-	0.5051	50.51%
Glucocorticoid receptor binding	-	0.4752	47.52%
Aromatase binding	-	0.6293	62.93%
PPAR gamma	+	0.6488	64.88%
Honey bee toxicity	-	0.9603	96.03%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	+	0.6724	67.24%
Fish aquatic toxicity	+	0.8953	89.53%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	63.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	97.53%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.77%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.61%	97.21%
CHEMBL230	P35354	Cyclooxygenase-2	88.47%	89.63%
CHEMBL239	Q07869	Peroxisome proliferator-activated receptor alpha	88.44%	90.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.52%	96.95%
CHEMBL2581	P07339	Cathepsin D	85.21%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.66%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.24%	96.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.47%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.90%	92.50%
CHEMBL221	P23219	Cyclooxygenase-1	80.87%	90.17%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.28%	86.67%

Plants that contains it

• Achillea nana
• Aconitum napellus
• Aglaia odorata
• Aristolochia fontanesii
• Astragalus bisulcatus
• Baccharoides lasiopus
• Bidens pilosa
• Boenninghausenia albiflora
• Bothriocline ripensis
• Brachyglottis bidwillii
• Calea lantanoides
• Chromolaena odorata
• Cibotium barometz
• Coronilla cretica
• Daphne odora
• Drosera indica
• Drummondita hassellii
• Ephedra distachya
• Flindersia xanthoxyla
• Galium mollugo
• Gardenia imperialis
• Glycyrrhiza glabra
• Gomesa radicans
• Grindelia scorzonerifolia
• Lantana ukambensis
• Lepidium graminifolium
• Lonchocarpus atropurpureus
• Pinus flexilis
• Psilotum nudum
• Rydingia limbata
• Senegalia mellifera
• Typha latifolia
• Uncaria sterrophylla
• Vicia amoena

Cross-Links

• PubChem: 5367460
• NPASS: NPC10316
• LOTUS: LTS0134186
• wikiData: Q27158118