ECMDB: alpha-Linolenic acid (ECMDB01388) (M2MDB000365)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (57)

Record Information

Version

2.0

Creation Date

2012-05-31 13:51:24 -0600

Update Date

2015-10-02 02:25:49 -0600

Secondary Accession Numbers

ECMDB01388

Identification

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. Omega-3 fatty acids get their name based on the location of one of their first double bond. 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). Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism. Alpha linolenic acid and other omega 3 fatty acids may regulate gene expression by interacting with specific transcription factors. ALA is an intermediate in alpha-Linolenic acid metabolism and biosynthesis of unsaturated fatty acids pathway in E. coli (KEGG compound: C06427).

Structure

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

Synonyms:

(9,12,15)-linolenate
(9,12,15)-linolenic acid
(9E,12E,15E)-9,12,15-Octadecatrienoate
(9E,12E,15E)-9,12,15-Octadecatrienoic acid
(9Z,12Z,15Z)-Octadecatrienoate
(9Z,12Z,15Z)-Octadecatrienoic acid
(Z,Z,Z)-9,12,15-Octadecatrienoate
(Z,Z,Z)-9,12,15-Octadecatrienoic acid
9,12,15-Octadecatrienoate
9,12,15-Octadecatrienoic acid
9-cis,12-cis,15-cis-Octadecatrienoate
9-cis,12-cis,15-cis-Octadecatrienoic acid
9Z,12Z,15Z-octadecatrienoate
9Z,12Z,15Z-octadecatrienoic acid
A-Linolenate
A-Linolenic acid
All-cis-9,12,15-Octadecatrienoate
All-cis-9,12,15-Octadecatrienoic acid
alpha-Linolenate
Alpha-Linolenic acid
Cis,cis,cis-9,12,15-Octadecatrienoate
Cis,cis,cis-9,12,15-Octadecatrienoic acid
Cis-9,12,15-Octadecatrienoate
Cis-9,12,15-Octadecatrienoic acid
Industrene 120
Linolenate
Linolenic acid
α-Linolenate
α-Linolenic acid

Chemical Formula:

C₁₈H₃₀O₂

Weight:

Average: 278.4296
Monoisotopic: 278.224580204

InChI Key:

DTOSIQBPPRVQHS-UHFFFAOYSA-N

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)

CAS number:

463-40-1

IUPAC Name:

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

Traditional IUPAC Name:

α linolenic acid

SMILES:

CCC=CCC=CCC=CCCCCCCCC(O)=O

Chemical Taxonomy

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 )

Physical Properties

State:

Liquid

Charge:

-1

Melting point:

-16.5 °C

Experimental Properties:

Property	Value	Source
LogP:	6.46 [SANGSTER (1993)]	PhysProp

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	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Phosphatidylcholine + Water <> 2-Acyl-sn-glycero-3-phosphocholine + alpha-Linolenic acid
phosphatidylcholine(1+) > alpha-Linolenic acid + Alpha-Linolenic acid

SMPDB Pathways:

Not Available

KEGG Pathways:

Biosynthesis of unsaturated fatty acids ec01040
alpha-Linolenic acid metabolism ec00592

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-052f-7900000000-8765cf82603feb1b448f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-004i-9300000000-302519a616eaed5fcc59	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-005c-9800000000-2d44b3c70e2992b9a812	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-7900000000-8765cf82603feb1b448f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-9300000000-302519a616eaed5fcc59	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-005c-9800000000-2d44b3c70e2992b9a812	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052f-5900000000-28710ea35f196c595e03	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052e-6950000000-27037263e74c8119ead0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ds-6931000000-657fa0cc66a206a36409	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-004i-0190000000-aee97e9ea2c7f0783adf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-05nb-9500000000-fb92aefc701027239359	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aru-9100000000-a5dddfe6f629d1371fac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-2b7bea03a685454dd135	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0090000000-53ddfaed6ce13c37d957	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-e5350a66361bc63d1071	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-5731aa5e301022c06813	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0091010000-6922411e48d747e592b5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-a18b573ad888d048efa6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-2b7bea03a685454dd135	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-e5350a66361bc63d1071	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-5731aa5e301022c06813	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-004i-0090000000-1d391027db3704d71cb9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-00lr-9210000000-41acd8a55f52afec6d79	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive	splash10-014i-9000000000-a976b4a80a07eb2c4641	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-497eddf5d738a45f83fb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-0c00ca98901526cb2e26	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-1090000000-35ffce9343fe0d15ea0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-004i-0090000000-373584fbab950d6676cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0090000000-ae1f482177d0e208165e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00o0-5690000000-20804c8382f14ff0ccf4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-8930000000-9d5e342b1351adc71c20	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-4d3e8d1180800a7b4ed5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1090000000-67ab14c068a142dd3c30	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-403c610d63380e63109a	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi. Preparation of a-linolenic acid from linseed oil. Zhengzhou Gongcheng Xueyuan Xuebao (2004), 25(3), 13-15.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	27432
HMDB ID	HMDB01388
Pubchem Compound ID	860
Kegg ID	C06427
ChemSpider ID	4445949
Wikipedia	Linolenic acid
BioCyc ID	LINOLENIC_ACID
EcoCyc ID	LINOLENIC_ACID

Enzymes

Protein Details

1. Phospholipase A1

General function:: Involved in phospholipase activity
Specific function:: Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:: pldA
Uniprot ID:: P0A921
Molecular weight:: 33163

Reactions

Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.

alpha-Linolenic acid (ECMDB01388) (M2MDB000365)

Structure for #<Compound:0xa18444b8>

Enzymes

Reactions