Showing Compound alpha-Linolenic acid (FDB012462)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:11 UTC

Update date

2020-09-17 15:31:13 UTC

Primary ID

FDB012462

Secondary Accession Numbers

FDB031277

Chemical Information

FooDB Name

alpha-Linolenic acid

Description

alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Omega-3 fatty acids get their name based on the location of one of their first double bonds. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are rich in alpha-linolenic acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of several genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Patients with isovaleric acidemia have a defect in leucine catabolism resulting from a deficiency in the enzyme isovaleryl-CoA dehydrogenase. These patients do well on a low protein/low leucine diet but a low protein diet can lead to deficiencies in essential fatty acids, such as alpha-linolenic acid ( https://doi.org/10.1038/ejcn.2016.100).

CAS Number

463-40-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(9,12,15)-Linolenic acid	ChEBI
(9Z,12Z,15Z)-Octadecatrienoic acid	ChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acid	ChEBI
9,12,15-Octadecatrienoic acid	ChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acid	ChEBI
ALA	ChEBI
all-cis-9,12,15-Octadecatrienoic acid	ChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acid	ChEBI
cis-Delta(9,12,15)-Octadecatrienoic acid	ChEBI
Linolenic acid	ChEBI
Linolenate	Kegg
alpha-Linolenate	Kegg
(9,12,15)-Linolenate	Generator
(9Z,12Z,15Z)-Octadecatrienoate	Generator
(Z,Z,Z)-9,12,15-Octadecatrienoate	Generator
9,12,15-Octadecatrienoate	Generator
9-cis,12-cis,15-cis-Octadecatrienoate	Generator
all-cis-9,12,15-Octadecatrienoate	Generator
cis,cis,cis-9,12,15-Octadecatrienoate	Generator
cis-delta(9,12,15)-Octadecatrienoate	Generator
cis-Δ(9,12,15)-octadecatrienoate	Generator
cis-Δ(9,12,15)-octadecatrienoic acid	Generator
a-Linolenate	Generator
a-Linolenic acid	Generator
Α-linolenate	Generator
Α-linolenic acid	Generator
alpha Linolenic acid	MeSH
cis-9,12,15-Octadecatrienoate	HMDB
cis-9,12,15-Octadecatrienoic acid	HMDB
Industrene 120	HMDB
FA(18:3(9Z,12Z,15Z))	HMDB
FA(18:3n3)	HMDB
α-Linolenic acid	biospider
9,12,15-Octadecatrienoic acid, (Z,Z,Z)-	biospider
9Z,12Z,15Z-Octadecatrienoate	biospider
9Z,12Z,15Z-Octadecatrienoic acid	biospider
alpha-Linolenic acid	biospider
cis-δ(9,12,15)-octadecatrienoate	Generator
cis-δ(9,12,15)-octadecatrienoic acid	Generator
α-linolenate	Generator
α-linolenic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.62	ALOGPS
logP	6.06	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	89.64 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H30O2

IUPAC name

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

InChI Identifier

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

Isomeric SMILES

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

Average Molecular Weight

278.4296

Monoisotopic Molecular Weight

278.224580204

Classification

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

omega-3 fatty acid (CHEBI:27432 )
linolenic acid (CHEBI:27432 )
Unsaturated fatty acids (C06427 )
Polyunsaturated fatty acids (C06427 )
Unsaturated fatty acids (LMFA01030152 )

Ontology

Physiological effect

Health effect:

Health condition:

Essential hypertension

Vascular disorders:

Hypertension

Cancer:

Thyroid cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Foods

Nuts and legumes:

Nuts

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 77.65%; H 10.86%; O 11.49%	DFC
Melting Point	Mp -11.3°	DFC
Boiling Point	Bp0.05 125°	DFC
Experimental Water Solubility	Not Available
Experimental logP	6.46	SANGSTER (1993)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 0.92	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	alpha-Linolenic acid, 1 TMS, GC-MS Spectrum	splash10-052f-7900000000-8765cf82603feb1b448f	Spectrum
GC-MS	alpha-Linolenic acid, 1 TMS, GC-MS Spectrum	splash10-004i-9300000000-302519a616eaed5fcc59	Spectrum
GC-MS	alpha-Linolenic acid, 1 TMS, GC-MS Spectrum	splash10-005c-9800000000-2d44b3c70e2992b9a812	Spectrum
GC-MS	alpha-Linolenic acid, non-derivatized, GC-MS Spectrum	splash10-052f-7900000000-8765cf82603feb1b448f	Spectrum
GC-MS	alpha-Linolenic acid, non-derivatized, GC-MS Spectrum	splash10-004i-9300000000-302519a616eaed5fcc59	Spectrum
GC-MS	alpha-Linolenic acid, non-derivatized, GC-MS Spectrum	splash10-005c-9800000000-2d44b3c70e2992b9a812	Spectrum
GC-MS	alpha-Linolenic acid, non-derivatized, GC-MS Spectrum	splash10-052f-5900000000-28710ea35f196c595e03	Spectrum
Predicted GC-MS	alpha-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052e-6950000000-27037263e74c8119ead0	Spectrum
Predicted GC-MS	alpha-Linolenic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00ds-6931000000-657fa0cc66a206a36409	Spectrum
Predicted GC-MS	alpha-Linolenic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-004i-0190000000-aee97e9ea2c7f0783adf	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05nb-9500000000-fb92aefc701027239359	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aru-9100000000-a5dddfe6f629d1371fac	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-2b7bea03a685454dd135	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-53ddfaed6ce13c37d957	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-e5350a66361bc63d1071	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-5731aa5e301022c06813	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-a18b573ad888d048efa6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-2b7bea03a685454dd135	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-e5350a66361bc63d1071	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-5731aa5e301022c06813	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-004i-0090000000-1d391027db3704d71cb9	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-00lr-9210000000-41acd8a55f52afec6d79	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-014i-9000000000-a976b4a80a07eb2c4641	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-497eddf5d738a45f83fb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0c00ca98901526cb2e26	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-1090000000-35ffce9343fe0d15ea0d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0090000000-373584fbab950d6676cc	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0090000000-ae1f482177d0e208165e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00o0-5690000000-20804c8382f14ff0ccf4	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-8930000000-9d5e342b1351adc71c20	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-4d3e8d1180800a7b4ed5	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1090000000-67ab14c068a142dd3c30	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-403c610d63380e63109a	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

27432

Phenol-Explorer ID

Not Available

DrugBank ID

DB00132

HMDB ID

HMDB01388

CRC / DFC (Dictionary of Food Compounds) ID

CPM16-L:HHB80-W

EAFUS ID

Not Available

Dr. Duke ID

CIS-LINOLEIC-ACID|ALPHA-LINOLENIC-ACID|LINOLENIC-ACID

BIGG ID

48237

KNApSAcK ID

C00007247

HET ID

LNL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1045911

SuperScent ID

Not Available

Wikipedia ID

Alpha-Linolenic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
5-alpha-reductase inhibitor	50781	An agent that blocks the conversion of testosterone to dihydrotestosterone, reducing androgenic effects. Therapeutically, it treats benign prostatic hyperplasia, androgenetic alopecia, and acne, by decreasing prostate size, promoting hair growth, and minimizing sebaceous gland activity.	DUKE
Anti-aggregant		An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.	DUKE
Anti hypertensive	52217	An agent that lowers blood pressure, reducing the risk of cardiovascular disease. It plays a biological role in relaxing blood vessels, decreasing cardiac workload, and improving blood flow. Therapeutically, it's used to manage hypertension, heart failure, and stroke, with key medical applications in preventing organ damage and improving overall cardiovascular health.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti leukotriene-D4	35222	An agent that blocks the action of leukotriene D4, reducing inflammation and bronchoconstriction. Therapeutically, it's used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting leukotriene-mediated responses, providing relief from symptoms such as wheezing, coughing, and shortness of breath.	DUKE
Anti-menorrhagic	52217	An agent that reduces heavy menstrual bleeding, playing a biological role in regulating menstrual flow. Therapeutically, it is used to treat menorrhagia, with key medical applications including managing excessive uterine bleeding, dysmenorrhea, and menstrual disorders.	DUKE
Anti metastatic	35610	An agent that inhibits cancer cell spread, reducing tumor metastasis. It plays a biological role in blocking cell migration and invasion, and has therapeutic applications in cancer treatment. Key medical uses include preventing cancer recurrence and improving survival rates in patients with various types of cancer.	DUKE
Anti-prostatitic		An agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Immunostimulant	50847	An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.	DUKE
Lymphocytogenic		An agent that stimulates production of lymphocytes, enhancing immune response. Therapeutically, it promotes lymphocyte growth, aiding in cancer treatment and immune system disorders. Key medical uses include immunotherapy and treating lymphopenia, or low lymphocyte count, to boost the body's natural defense mechanisms.	DUKE
Tyrosine kinase inhibitor		An agent that blocks the enzymatic activity of tyrosine kinases, enzymes responsible for the activation of many proteins involved in signal transduction pathways regulating cell growth and survival. Therapeutically, tyrosine kinase inhibitors are widely used in the treatment of various cancers and proliferative diseases, by halting aberrant signaling that drives tumor progression and pathological tissue remodeling.	DUKE
Prostaglandin synthesis inhibitor	35222	An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).	DUKE
Vasodilator	35620	An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2
Elongation of very long chain fatty acids protein 4	ELOVL4	Q9GZR5

Pathways

Name	SMPDB Link	KEGG Link
Alpha Linolenic Acid and Linoleic Acid Metabolism	SMP00018	map00592

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
faint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755