Bovine Metabolome Database: Showing metabocard for 8,11,14-Eicosatrienoic acid (BMDB0002925)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:02:10 UTC

Update Date

2020-06-04 20:33:32 UTC

BMDB ID

BMDB0002925

Secondary Accession Numbers

BMDB02925

Metabolite Identification

Common Name

8,11,14-Eicosatrienoic acid

Description

8,11,14-Eicosatrienoic acid, also known as (Z,Z,Z)-8,11,14-icosatrienoate or dihomo-gamma-linolenic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 8,11,14-Eicosatrienoic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. 8,11,14-Eicosatrienoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 8,11,14-Eicosatrienoic acid participates in a number of enzymatic reactions, within cattle. In particular, 8,11,14-Eicosatrienoic acid can be biosynthesized from Gamma-linolenic acid through its interaction with the enzyme elongation OF very long chain fatty acids protein 5. In addition, 8,11,14-Eicosatrienoic acid can be converted into arachidonic acid; which is mediated by the enzyme fatty acid desaturase 1. In cattle, 8,11,14-eicosatrienoic acid is involved in the metabolic pathway called the Alpha linolenic Acid and linoleic Acid metabolism pathway. 8,11,14-Eicosatrienoic acid has been found to be associated with the diseases known as colorectal cancer; also 8,11,14-eicosatrienoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(8Z,11Z,14Z)-Icosatrienoic acid	ChEBI
(Z,Z,Z)-8,11,14-Eicosatrienoic acid	ChEBI
(Z,Z,Z)-8,11,14-Icosatrienoate	ChEBI
(Z,Z,Z)-8,11,14-Icosatrienoic acid	ChEBI
20:3, N-6,9,12 all-cis	ChEBI
8,11,14-Eicosatrienoic acid	ChEBI
8C,11C,14C-Eicosatrienoic acid	ChEBI
8C,11C,14C-Eicosatriensaeure	ChEBI
8Z,11Z,14Z-Eicosatrienoic acid	ChEBI
all-cis-8,11,14-Eicosatrienoic acid	ChEBI
all-cis-8,11,14-Icosatrienoic acid	ChEBI
all-cis-Eicosa-8,11,14-trienoic acid	ChEBI
all-cis-Eicosa-8,11,14-triensaeure	ChEBI
C20:3, N-6,9,12 all-cis	ChEBI
cis,cis,cis-8,11,14-Eicosatrienoic acid	ChEBI
DGLA	ChEBI
Eicosa-8Z,11Z,14Z-trienoic acid	ChEBI
gamma-Homolinolenic acid	ChEBI
Homo-gamma-linolenic acid	ChEBI
Homo-gamma-linolensaeure	ChEBI
(Z,Z,Z)-8,11,14-Eicosatrienoate	Kegg
8,11,14-Eicosatrienoate	Kegg
8,11,14-Icosatrienoate	Kegg
(8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid	Kegg
(8Z,11Z,14Z)-Icosatrienoate	Generator
8C,11C,14C-Eicosatrienoate	Generator
8Z,11Z,14Z-Eicosatrienoate	Generator
all-cis-8,11,14-Eicosatrienoate	Generator
all-cis-8,11,14-Icosatrienoate	Generator
all-cis-Eicosa-8,11,14-trienoate	Generator
cis,cis,cis-8,11,14-Eicosatrienoate	Generator
Eicosa-8Z,11Z,14Z-trienoate	Generator
g-Homolinolenate	Generator
g-Homolinolenic acid	Generator
gamma-Homolinolenate	Generator
Γ-homolinolenate	Generator
Γ-homolinolenic acid	Generator
Homo-g-linolenate	Generator
Homo-g-linolenic acid	Generator
Homo-gamma-linolenate	Generator
Homo-γ-linolenate	Generator
Homo-γ-linolenic acid	Generator
Homo-g-linolensaeure	Generator
Homo-γ-linolensaeure	Generator
8,11,14-Icosatrienoic acid	Generator
(8Z,11Z,14Z)-Icosa-8,11,14-trienoate	Generator
Dihomo-g-linolenate	Generator
Dihomo-g-linolenic acid	Generator
Dihomo-gamma-linolenate	Generator
Dihomo-γ-linolenate	Generator
Dihomo-γ-linolenic acid	Generator
Dihomogammalinolenic acid	HMDB
Dihomo gamma linolenic acid	HMDB
Homo-gamma linolenic acid	HMDB
Homo gamma linolenic acid	HMDB
Linolenic acid, homo-gamma	HMDB
8,11,14 Eicosatrienoic acid	HMDB
(Z,Z,Z)-Icosatri-8,11,14-enoate	HMDB
(Z,Z,Z)-Icosatri-8,11,14-enoic acid	HMDB
8,11,14-all-cis-Eicosatrienoate	HMDB
8,11,14-all-cis-Eicosatrienoic acid	HMDB
Bishomo-gamma-linolenate	HMDB
Bishomo-gamma-linolenic acid	HMDB
cis-8,11,14-Eicosatrienoate	HMDB
cis-8,11,14-Eicosatrienoic acid	HMDB
cis-8,cis-11,cis-14-Eicosatrienoate	HMDB
cis-8,cis-11,cis-14-Eicosatrienoic acid	HMDB
Eicosatrienoate	HMDB
Eicosatrienoic acid	HMDB
Acid, dihomo-gamma-linolenic	HMDB
DHLA	HMDB
Acid, dihomogammalinolenic	HMDB
Acid, homo-gamma linolenic	HMDB
Dihomolinolenate	HMDB
Dihomolinolenic acid	HMDB
FA(20:3(8Z,11Z,14Z))	HMDB
Dihomo-linolenate	HMDB
Dihomo-linolenic acid	HMDB
FA(20:3n6)	HMDB
dihomo-gamma-Linolenic acid	ChEBI

Chemical Formula

C₂₀H₃₄O₂

Average Molecular Weight

306.4828

Monoisotopic Molecular Weight

306.255880332

IUPAC Name

(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid

Traditional Name

dihomo-gamma-linolenic acid

CAS Registry Number

1783-84-2

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-

InChI Key

HOBAELRKJCKHQD-QNEBEIHSSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain 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

long-chain fatty acid (CHEBI:53486 )
icosatrienoic acid (CHEBI:53486 )
Polyunsaturated fatty acids (C03242 )
Unsaturated fatty acids (LMFA01030158 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.24	ALOGPS
logP	6.95	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.89	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	15	ChemAxon
Refractivity	98.84 m³·mol⁻¹	ChemAxon
Polarizability	39.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9570000000-cd036d3430a12b16dfb6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-022i-9542000000-c2f35f73d1bcbb0128a3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
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, Positive (Annotated)	splash10-0a4i-0019000000-38de24f5141b8fd24471	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-066v-9700000000-ea3e83fc76a5e8bf96a0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0k96-9200000000-2b1245d775cb6a9290a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0090000000-8151054828665541898d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-05e9-0491000000-a09d13fe83820b375121	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-052e-0692000000-aba537ad7f934032649f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0adj-0920000000-14556c974d2f5a8357cd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-059i-0791000000-db1fa7d2bf17ecf40820	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0910000000-23e553ce4de5f9a92f32	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0196000000-0cb348afdbc2bfa250ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-5891000000-413e3aa407f0e1cb6465	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052g-9760000000-b7aed55f7d8853fa6cf7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0029000000-d1aef216444b744a8339	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1079000000-1eb636eb88d281beeffe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9230000000-c1354a863e0181f2b709	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-4496000000-d2c86b500de1b25b89bd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5i-8920000000-c9e205f0c9bc159b6e85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o4-9300000000-6f4b5c73d4ea8dd6ce7c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-a547ddaba8c204ad4b7f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-2069000000-bf269de6180612c37971	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9220000000-00dffbb43465bcaae37f	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Epidermis
Milk
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Alpha Linolenic Acid and Linoleic Acid Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	2577.631 +/- 619.937 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Milk	Detected and Quantified	2447.118 +/- 522.0518 uM	Not Specified	Not Specified	Normal	M. Ferrand et al....	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002925

DrugBank ID

DB00154

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023082

KNApSAcK ID

Not Available

Chemspider ID

4444199

KEGG Compound ID

C03242

BioCyc ID

Not Available

BiGG ID

41475

Wikipedia Link

Dihomo-γ-linolenic acid

METLIN ID

259

PubChem Compound

5280581

PDB ID

Not Available

ChEBI ID

53486

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]
Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987. [PubMed:19038946 ]
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.

Enzymes

Enzyme Details

1. Acyl-CoA 6-desaturase

General function:: Lipid transport and metabolism
Specific function:: Acts as a fatty acyl-coenzyme A (CoA) desaturase that introduces a cis double bond at carbon 6 of the fatty acyl chain. Involved in biosynthesis of highly unsaturated fatty acids (HUFA) from the essential polyunsaturated fatty acids (PUFA) linoleic acid (LA) (18:2n-6) and alpha-linolenic acid (ALA) (18:3n-3) precursors. Catalyzes the first and rate limiting step in this pathway which is the desaturation of LA (18:2n-6) and ALA (18:3n-3) into gamma-linoleate (GLA) (18:3n-6) and stearidonate (18:4n-3), respectively (By similarity). Subsequently, in the biosynthetic pathway of HUFA n-3 series, desaturates tetracosapentaenoate (24:5n-3) to tetracosahexaenoate (24:6n-3), which is then converted to docosahexaenoate (DHA)(22:6n-3), an important lipid for nervous system function (By similarity). Desaturates palmitate to produce the mono-unsaturated fatty acid sapienate, the most abundant fatty acid in sebum (By similarity). Also desaturates (11E)-octadecenoate (trans-vaccenoate)(18:1n-9), a metabolite in the biohydrogenation pathway of LA (18:2n-6) (By similarity).
Gene Name:: FADS2
Uniprot ID:: A4FV48
Molecular weight:: 52533.0

Reactions

8,11,14-Eicosatrienoic acid → Arachidonic acid	details

Enzyme Details

2. Elongation of very long chain fatty acids protein 5

General function:: Not Available
Specific function:: Catalyzes the first and rate-limiting reaction of the four reactions that constitute the long-chain fatty acids elongation cycle. This endoplasmic reticulum-bound enzymatic process allows the addition of 2 carbons to the chain of long- and very long-chain fatty acids (VLCFAs) per cycle. Condensing enzyme that acts specifically toward polyunsaturated acyl-CoA with the higher activity toward C18:3(n-6) acyl-CoA. May participate in the production of monounsaturated and of polyunsaturated VLCFAs of different chain lengths that are involved in multiple biological processes as precursors of membrane lipids and lipid mediators (By similarity). In conditions where the essential linoleic and alpha linoleic fatty acids are lacking it is also involved in the synthesis of Mead acid from oleic acid (By similarity).
Gene Name:: ELOVL5
Uniprot ID:: Q2KJD9
Molecular weight:: 35377.0

Reactions

Gamma-Linolenic acid → 8,11,14-Eicosatrienoic acid	details

Showing metabocard for 8,11,14-Eicosatrienoic acid (BMDB0002925)

Structure for BMDB0002925 (8,11,14-Eicosatrienoic acid)

Enzymes

Reactions

Reactions