Linolenic acid - Compound Card

Linolenic acid

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Linolenic acid

Structure
Zoomed Structure
  • Family: Plantae - Myrsinaceae
  • Kingdom: Plantae
  • Class: Lipid
    • Subclass: Fatty Acid
Canonical Smiles 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-
InChIKey DTOSIQBPPRVQHS-PDBXOOCHSA-N
Formula C18H30O2
HBA 1
HBD 1
MW 278.44
Rotatable Bonds 13
TPSA 37.3
LogP 5.66
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 278.22
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Apium graveolens Apiaceae Plantae 4045
2 Juniperus phoenicea Cupressaceae Plantae 61308
3 Cynara cardunculus Asteraceae Plantae 4265
4 Embelia schimperi Myrsinaceae Plantae 2595069

Showing of synonyms

  • Tessema EN, Neubert R, et al. (2018). Anthelmintic activity-guided fractionation and GC-MS analysis of extracts from Embelia schimperi fruits. International Journal of Applied Research in Natural Products,2018,11(1),11-16.. [View] [PubMed]
  • Nasri N, Tlili N, et al. (2011). Chemical compounds from Phoenician juniper berries (Juniperus phoenicea). Natural Product Research,2011,25(18),1733-1742. [View]
  • Farag MA, El-Ahmady SH, et al. (2013). Metabolomics driven analysis of artichoke leaf and its commercial products via UHPLC–q-TOF-MS and chemometrics. Phytochemistry,2013,95,177-187. [View] [PubMed]
  • MacLeod AJ, MacLeod G, et al. (1988). Volatile aroma constituents of celery. Phytochemistry,1988,27(2),373-375. [View]
Pubchem: 5280934
Kegg Ligand: C06427
Chebi: 27432
Nmrshiftdb2: 60018784
Metabolights: MTBLC27432
Chembl: CHEMBL8739
Drugbank: DB00132
Pdb Ligand: LNL
Bindingdb: 50240347
CPRiL: 1042

No scaffolds available.

Anthelmintic

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.35
Plasma Protein Binding
64.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-1.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.28
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.0
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.03
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Toxic
NR-TR
Safe
T. Pyriformis
0.88
Rat (Acute)
1.31
Rat (Chronic Oral)
2.35
Fathead Minnow
4.08
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
350.96
Hydration Free Energy
-4.89
Log(D) at pH=7.4
2.61
Log(P)
6.29
Log S
-3.75
Log(Vapor Pressure)
-5.87
Melting Point
-10.23
pKa Acid
5.87
pKa Basic
7.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.9913
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.9913
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.9023
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.9023
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8506
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8506
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8297
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8297
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7794
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7794
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7749
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 2 0.7749
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7584
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7584
12-oxophytodienoate reductase 1 Q9XG54 OPR1_SOLLC Solanum lycopersicum 2 0.7547
12-oxophytodienoate reductase 1 Q9XG54 OPR1_SOLLC Solanum lycopersicum 2 0.7547
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7238
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7238
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7189
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7189
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7185
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7185
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7185
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7185
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7111
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7111
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7109
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7109
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7089
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7089
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7028
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7028
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7021
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7021
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7019
Isopenicillin N synthase P05326 IPNS_EMENI Emericella nidulans 2 0.7019
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7018
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7018

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