CAS 463-40-1|Alpha-Linolenic Acid|alpha-Linolenate|α-linolenic acid|9,12,15-Octadecatrienoic acid|(9Z,12Z,15Z)-Octadecatrienoic acid|linolenate|(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid|ALA|Linol...

General Information

Structure

Molecular Formula

C₁₈H₃₀O₂

Molecular Mass

278.4296

Exact Mass

278.2245802

Charge

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

Canonic Smiles

CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O

Isomeric Smiles

OC(=O)CCCCCCC/C=C\C/C=C\C/C=C\CC

Calculated Properties

JChem

LogD (pH = 7.4)

3.68

LogD (pH = 5.5)

5.43

Log P

6.06

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

4.99

Polar Surface Area

37.30

Polarizability

35.00

Molar Refractivity

89.64

LOG S

-7.17

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

linolenateAlpha-Linolenic Acidalpha-Linolenate9,12,15-Octadecatrienoic acidALA(9Z,12Z,15Z)-Octadecatrienoic acid(Z,Z,Z)-Octadeca-9,12,15-trienoic Acid9,12,15-all-cis-Octadecatrienoic AcidLinolenic Acidcis-Δ9,12,15-Octadecatrienoic acid(all-Z)-9,12,15-Octadecatrienoic Acidα-Linolenic Acidall-cis-9,12,15-Octadecatrienoic Acid(9Z,12Z,15Z)-9,12,15-Octadecatrienoic Acid(9Z,12Z,15Z)-Octadecatrienoic acidalpha-linolenic acidALAcis-Delta(9,12,15)-octadecatrienoic acidall-cis-9,12,15-octadecatrienoic acidalpha-linolenic acidALPHA-LINOLENIC ACIDlinolenic acid9-cis,12-cis,15-cis-octadecatrienoic acidalpha-Linolenic acid9,12,15-Octadecatrienoic acid(Z,Z,Z)-9,12,15-octadecatrienoic acidcis,cis,cis-9,12,15-octadecatrienoic acid(9,12,15)-linolenic acid

IUPAC Traditional name

α-linolenic acid α linolenic acid

IUPAC name

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

Names and Identifiers

Registration numbers

PubChem CID

5280934

CAS Number

463-40-1

PubChem SID

465076201609634818144514

BRENDA Ligand Database

69761018674260743291413439305522669642620901462632287204393545938

PubMed Citation Links

113041271023262519269799243200562485565524639012

BKMS React Database

90146426074593866964453132287204393026204893461145522

MetaboLights Database

MTBLS3769MTBLS363MTBLS1796MTBLS699MTBLS1217MTBLS2397MTBLS750MTBLS334MTBLS399MTBLS2633MTBLS93MTBLS2096MTBLS3927MTBLS1693MTBLS2597

UniProt Database

B9GBM3Q90508Q9J5D0Q894B9A4L9J0A4YZK6Q9H8G2P25152P32639Q9PI72C0RE73Q0J5F8Q5PBK2Q5HUZ4Q92043

Protein Data Bank

4e1g1fk62byo

SABIO-RK Database

161641496398501358314688

CompTox Database

KNApSAcK Database

MetaCyc Database

KEGG ID

SureChEMBL Database

CHEMBL

Reaxys Registry

LIPID MAPS Instance

Reactom Database

R-HSA-1989753R-HSA-1989746R-HSA-1989750R-HSA-1989765R-HSA-1989778R-HSA-1592238R-HSA-1801587R-HSA-383313R-HSA-1989777R-HSA-560517R-HSA-1989756R-HSA-1989751R-HSA-1989747R-HSA-1989767R-HSA-1989764

PDBeChem Database

LNL

Patent number

US2008166781EP1685834EP1676488EP1961311US2007196445US2008176956US2007265341US2008058418EP1854462US2005014826US2006035350US2004131648

CHEBI ID

CHEBI:27432CHEBI:43891CHEBI:22462CHEBI:10298

EnzymePortal Database

Q84K11

Golm Database

9c8cfa58-38c1-48a2-87c4-219bbe2863d681c9c091-4174-424d-a7c7-cd2077aab955034f849b-18a4-4a6a-97e3-1d03df4704e6bc4ee730-9980-4c61-8608-0b60886eafe7381c4fb1-00a1-45b4-af41-56c94f9b40ea

HMDB Database

DrugBank ID

Beilstein Number

Wikipedia Title

Drug Central Database

4,618

Gmelin ID

57558

BindingDB Database

50240347

Registration numbers

Properties

Physical Property

Solubility

0.000124 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]

Methanol

Chloroform

Hydrophobicity(logP)

5.8

Apperance

Colorless Oil

Product Information

Certificate of Analysis

Download link

Safety Information

Storage Condition

Refrigerator

MSDS Link

Download link

Properties

Related Proteins

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00132

Drug Groups

approved; nutraceutical

Description

Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. [Wikipedia]

Indication

For nutritional supplementation and for treating dietary shortage or imbalance.

Pharmacology

Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds. It is also called an omega-3 fatty acid, and is essential for all mammals. Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by 1) preventing arrhythmias that can lead to sudden cardiac death, 2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke, 3) decreasing serum triglyceride levels, 4) slowing the growth of atherosclerotic plaque, 5) improving vascular endothelial function, 6) lowering blood pressure slightly, and 7) decreasing inflammation. ALA deficiencies can lead to visual problems and sensory neuropathy. Scaly and hemorrhagic skin or scalp inflammations may also develop.

Affected Organisms

Humans and other mammals

References

• Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. [Pubmed]

• Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. [Pubmed]

• Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. [Pubmed]

• Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. [Pubmed]

• Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. [Pubmed]

External Links

• [Wikipedia]

TRC

L467650

An essential fatty acid. Occurs as the glyceride in most drying oils. Nutrient.

ChEBI

CHEBI:27432

A linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect.

Molecule Details

References

PubChem Literature

From Data Sources

• Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. Pubmed

• Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. Pubmed

• Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. Pubmed

• Tritt, K., et al.: J. Agric. Food Chem., 53, 5304 (1957)

• Orban, E., et al.: J. Food Sci., 68, 128 (1957)

• Folch, J., et al.: J. Biol. Chem., 226, 497 (1957)

References

Bioactivity

PubChem BioAssay

Bioactivity

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Calculated Properties

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