Natural Product (NP) Details

General Information of the NP (ID: NP8924)
Name
Alpha linolenic acid
Synonyms
linolenic acid; 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; 9-cis,12-cis,15-cis-Octadecatrienoic acid; 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-; (Z,Z,Z)-9,12,15-Octadecatrienoic acid; (9,12,15)-linolenic acid; Linolenic acid (8CI); alpha-Lnn; 9Z,12Z,15Z-Octadecatrienoic acid; Industrene 120; 9,12,15-Octadecatrienoic acid; CCRIS 656; (9Z,12Z,15Z)-Octadecatrienoic acid; UNII-0RBV727H71; .alpha.-Linolenic acid; CHEMBL8739; cis-delta9,12,15-Octadecatrienoic acid; AI3-23986; cis-Delta(9,12,15)-octadecatrienoic acid; (Z,Z,Z)-Octadeca-9,12,15-trienoic acid; CHEBI:27432; 0RBV727H71; MFCD00065720; LINOLENIC ACID (18:3 n-3); 9,12,15-all-cis-Octadecatrienoic acid; NCGC00091058-04; Linolenic acid, 99%; DSSTox_CID_5506; cis-9, cis-12, cis-15-octadecatrienoic acid; DSSTox_RID_77815; (9Z,12Z,15Z)octadeca-9,12,15-trienoic acid; DSSTox_GSID_25506; alpha-LA; CAS-463-40-1; SMR000857336; C18:3n-3,6,9; (9Z,12Z,15Z)-Octadecatrienoate; Linolenic acid, crude; cis,cis,cis-9,12,15-octadecatrienoate; a-Linolenate; cis-9,12,15-octadecatrienoic acid; cis,cis-9,12,15-Octadecatrienoic acid; (9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid; NSC 2042; alpha-linolenic-acid; EINECS 207-334-8; C18:3; Linolenic acid, >=99%; SCHEMBL15282; 9,12,15-Octadecatrienoate; BSPBio_001376; 68424-45-3; MLS001336029; MLS001336030; MLS002454413; BML3-B05; GTPL1049; Linolenic acid, ~70% (GC); DTXSID7025506; cid_5280934; cis-9,12,15-octadecatrienoate; NSC2042; FA005; HMS1361E18; HMS1791E18; HMS1989E18; HMS2233C13; HMS3402E18; HMS3649H05; Linolenic acid, analytical standard; CMC_7371; HY-N0728; NSC-2042; ZINC3802189; all-cis-9,15-Octadecatrienoic acid; Tox21_111071; Tox21_201727; Tox21_303322; all-cis-9,12,15-Octadecatrienoate; BDBM50240347; LMFA01030152; SBB069548; AKOS016008598; DB00132; (Z,Z,Z)-9,12,15-Octadecatrienoate; 9-cis,12-cis,15-cis-octadecatrienoate; IDI1_033846; Linolenic acid 10 microg/mL in Methanol; NCGC00091058-01; NCGC00091058-02; NCGC00091058-05; NCGC00091058-06; NCGC00091058-07; NCGC00091058-08; NCGC00091058-09; NCGC00091058-10; NCGC00257192-01; NCGC00259276-01; (all-Z)-9,12,15-Octadecatrienoic acid; 9,15-Octadecatrienoic acid, (Z,Z,Z)-; AS-57338; M621; ST072192; 9(Z),12(Z),15(Z)-Octadecatrienoic acid; cis-9,cis-12,cis-15-Octadecatrienoic acid; CS-0009741; L0050; cis,cis,cis-octadeca-9,12,15-trienoic acid; Octadecatrienoic acid, 9,12,15-(Z,Z,Z)-; A-8311; C06427; Linolenic acid, Vetec(TM) reagent grade, 98%; L000707; Q256502; SR-01000838327; SR-01000838327-2; 2DCD0473-E5CC-47BB-A0A4-95899AFF6C4B; BRD-K33396764-001-02-0; 9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- (9CI); UNII-0JXR8F0V1Q component DTOSIQBPPRVQHS-PDBXOOCHSA-N; UNII-5U9XZ261ER component DTOSIQBPPRVQHS-PDBXOOCHSA-N; UNII-71M78END5S component DTOSIQBPPRVQHS-PDBXOOCHSA-N; UNII-96GS7P39SN component DTOSIQBPPRVQHS-PDBXOOCHSA-N; UNII-F85N2YHE4E component DTOSIQBPPRVQHS-PDBXOOCHSA-N; UNII-HBA528N3PW component DTOSIQBPPRVQHS-PDBXOOCHSA-N; alpha-Linolenic acid, 1.0 mg/mL in ethanol, certified reference material
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Species Origin Perilla frutescens ...     Click to Show/Hide
Perilla frutescens
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Perilla
Species: Perilla frutescens
Disease Ulcerative colitis [ICD-11: DD71] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.054
 
MDCK Permeability
 -4.81
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 -0.465
 
PPB
 98.2%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +++
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 +++
CYP2C8 inhibitor
 +++
HLM Stability
 - - -
 
Excretion
CLplasma
 4.648
 
T1/2
 0.354
Toxicity
DILI
 - - -
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - - -
 
Respiratory
 +++
 
Human Hepatotoxicity
 - - -
 
Ototoxicity
 - - -
 
Drug-induced Nephrotoxicity
 -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 - - -
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C18H30O2
PubChem CID
5280934
Canonical SMILES
CCC=CCC=CCC=CCCCCCCCC(=O)O
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
CAS Number
CAS 463-40-1
ChEBI ID
CHEBI:27432
Herb ID
HBIN033339
SymMap ID
SMIT00044
TCMSP ID
MOL000432
TTD Drug ID
D0C5SV
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Riluzole      Motor neuron disease     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression KCNK2  Molecule Info 
Pathway MAP
Up-regulation Expression KCNK4  Molecule Info 
Pathway MAP
                    In-vivo Model Focal ischemia was induced in adult male C57/Bl6 mice by occlusion of the left middle cerebral artery (MCA) using an intraluminal filament technique.
                    Experimental
                    Result(s)		 Alpha-linolenic acid and riluzole treatment confer cerebral protection and improve survival after focal brain ischemia.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Gentamicin      Bacterial infection     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression NOS2  Molecule Info 
Pathway MAP
                    In-vivo Model Eight-week-old balb/c albino male mice were used in this study.
                    Experimental
                    Result(s)		 The gentamicin administration causes nephrotoxicity and the use of alpha-linolenic acid can be helpful against this toxic effect.
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression NOS2  Molecule Info 
Pathway MAP
                    In-vivo Model Male BALB/c albino mice weighing 30 g were used in this study.
                    Experimental
                    Result(s)		 ALA, an n-3 fatty acid, has a protective effect in mice renal tissue.
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
                    In-vivo Model Male Sprague-Dawley rats weighing 220+ 20 were used in this study.
                    Experimental
                    Result(s)		 Alpha-Linolenic acid attenuates doxorubicin-induced cardiotoxicity in rats through suppression of oxidative stress and apoptosis.
Target and Pathway
Target(s) Gprotein coupled receptor 120 (GPR120)  Molecule Info  [6]
Gprotein coupled receptor 40 (GPR40)  Molecule Info  [7]
Prostaglandin G/H synthase 2 (COX-2)  Molecule Info  [8]
BioCyc Aspirin-triggered lipoxin biosynthesis Click to Show/Hide
2 Aspirin triggered resolvin D biosynthesis
3 C20 prostanoid biosynthesis
4 Aspirin triggered resolvin E biosynthesis
KEGG Pathway Insulin secretion Click to Show/Hide
2 Arachidonic acid metabolism
3 Metabolic pathways
4 NF-kappa B signaling pathway
5 VEGF signaling pathway
6 TNF signaling pathway
7 Retrograde endocannabinoid signaling
8 Serotonergic synapse
9 Ovarian steroidogenesis
10 Oxytocin signaling pathway
11 Regulation of lipolysis in adipocytes
12 Leishmaniasis
13 Pathways in cancer
14 Chemical carcinogenesis
15 MicroRNAs in cancer
16 Small cell lung cancer
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TSH Signaling Pathway
3 IL4 Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL5 Signaling Pathway
Panther Pathway Endothelin signaling pathway Click to Show/Hide
2 Inflammation mediated by chemokine and cytokine signaling pathway
3 Toll receptor signaling pathway
4 CCKR signaling map ST
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
Pathway Interaction Database Calcineurin-regulated NFAT-dependent transcription in lymphocytes Click to Show/Hide
2 S1P1 pathway
3 C-MYB transcription factor network
4 Signaling mediated by p38-alpha and p38-beta
5 Calcium signaling in the CD4+ TCR pathway
Reactome G alpha (q) signalling events Click to Show/Hide
2 Fatty Acids bound to GPR40 (FFAR1) regulate insulin secretion
WikiPathways GPCRs, Class A Rhodopsin-like Click to Show/Hide
2 Incretin Synthesis, Secretion, and Inactivation
3 Gastrin-CREB signalling pathway via PKC and MAPK
4 Integration of energy metabolism
5 GPCR ligand binding
6 GPCR downstream signaling
7 Prostaglandin Synthesis and Regulation
8 Arachidonic acid metabolism
9 Aryl Hydrocarbon Receptor
10 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
11 Spinal Cord Injury
12 Integrated Pancreatic Cancer Pathway
13 Eicosanoid Synthesis
14 Selenium Micronutrient Network
References
Reference 1 Alpha-Linolenic Acid Alleviates Dextran Sulfate Sodium-Induced Ulcerative Colitis in Mice. Inflammation. 2020 Oct;43(5):1876-1883.
Reference 2 Alpha-linolenic acid and riluzole treatment confer cerebral protection and improve survival after focal brain ischemia. Neuroscience. 2006;137(1):241-51.
Reference 3 Protective effect of alpha-linolenic acid on gentamicin-induced ototoxicity in mice. Somatosens Mot Res. 2017 Sep;34(3):145-150.
Reference 4 Alpha-linolenic acid confers protection on mice renal cells against cisplatin-induced nephrotoxicity. Cytotechnology. 2019 Oct;71(5):905-914.
Reference 5 Alpha-Linolenic acid attenuates doxorubicin-induced cardiotoxicity in rats through suppression of oxidative stress and apoptosis. Acta Biochim Biophys Sin (Shanghai). 2013 Oct;45(10):817-26.
Reference 6 Cloning and characterization of the rat free fatty acid receptor GPR120: in vivo effect of the natural ligand on GLP-1 secretion and proliferation of pancreatic beta cells. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jun;377(4-6):515-22.
Reference 7 Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. Nature. 2003 Mar 13;422(6928):173-6.
Reference 8 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
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