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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-05-01 17:29:32 UTC
Update Date2022-09-22 17:44:09 UTC
HMDB IDHMDB0060039
Secondary Accession Numbers
  • HMDB60039
Metabolite Identification
Common NameDihomo-alpha-linolenic acid
DescriptionDihomo-alpha-linolenic acid, also known as 11,14,17-eicosatrienoic acid, is a rare polyunsaturated fatty acid of the omega-3 series. In normal humans, it represents less than 0.25% of serum phospholipid fatty acids. However, it is one of the most active essential fatty acids when assayed for the inhibition of fatty acid elongation/desaturation reactions which convert dietary C-18 fatty acids to C-20 eicosanoid precursors. (http://www.caymanchem.com)
Structure
Data?1574702573
Synonyms
ValueSource
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoic acidChEBI
(11Z,14Z,17Z)-Icosa-11,14,17-trienoic acidChEBI
(Z,Z,Z)-11,14,17-Eicosatrienoic acidChEBI
11,14,17-Eicosatrienoic acidChEBI
11,14,17-Icosatrienoic acidChEBI
11C,14C,17C-Eicosatrienoic acidChEBI
11C,14C,17C-EicosatriensaeureChEBI
20:3, N-3,6,9 all-cisChEBI
all-cis-11,14,17-Eicosatrienoic acidChEBI
all-cis-Eicosa-11,14,17-trienoic acidChEBI
all-cis-Eicosa-11,14,17-triensaeureChEBI
C20:3, N-3,6,9 all-cisChEBI
cis,cis,cis-11,14,17-Eicosatrienoic acidChEBI
Eicosa-11Z,14Z,17Z-trienoic acidChEBI
Eicosatrienoic acidChEBI
ETAChEBI
ETEChEBI
(11Z,14Z,17Z)-Eicosa-11,14,17-trienoateGenerator
(11Z,14Z,17Z)-Icosa-11,14,17-trienoateGenerator
(Z,Z,Z)-11,14,17-EicosatrienoateGenerator
11,14,17-EicosatrienoateGenerator
11,14,17-IcosatrienoateGenerator
11C,14C,17C-EicosatrienoateGenerator
all-cis-11,14,17-EicosatrienoateGenerator
all-cis-Eicosa-11,14,17-trienoateGenerator
cis,cis,cis-11,14,17-EicosatrienoateGenerator
Eicosa-11Z,14Z,17Z-trienoateGenerator
EicosatrienoateGenerator
Dihomo-a-linolenateGenerator
Dihomo-a-linolenic acidGenerator
Dihomo-alpha-linolenateGenerator
Dihomo-α-linolenateGenerator
Dihomo-α-linolenic acidGenerator
DihomolinolenateHMDB
11,14,17-Eicosatrienoic acid, (Z,Z,Z)-isomerHMDB
Bishomo-a-linolenateHMDB
Bishomo-a-linolenic acidHMDB
Bishomo-alpha-linolenateHMDB
Bishomo-α-linolenateHMDB
Bishomo-α-linolenic acidHMDB
Bishomo-alpha-linolenic acidHMDB
Dihomo-linolenateHMDB
Dihomo-linolenic acidHMDB
Dihomolinolenic acidHMDB
FA(20:3(11Z,14Z,17Z))HMDB
FA(20:3n3)HMDB
Homo-alpha-linolenic acidHMDB
Homo-α-linolenic acidHMDB
Dihomo-alpha-linolenic acidHMDB
Chemical FormulaC20H34O2
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
IUPAC Name(11Z,14Z,17Z)-icosa-11,14,17-trienoic acid
Traditional Nameeicosatrienoic acid
CAS Registry Number17046-59-2
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(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/h3-4,6-7,9-10H,2,5,8,11-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-
InChI KeyAHANXAKGNAKFSK-PDBXOOCHSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.7e-05 g/LALOGPS
logP7.24ALOGPS
logP6.95ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity98.84 m³·mol⁻¹ChemAxon
Polarizability38.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.68731661259
DarkChem[M-H]-184.65131661259
DeepCCS[M+H]+182.48730932474
DeepCCS[M-H]-180.12930932474
DeepCCS[M-2H]-213.01630932474
DeepCCS[M+Na]+188.5830932474
AllCCS[M+H]+184.532859911
AllCCS[M+H-H2O]+181.632859911
AllCCS[M+NH4]+187.232859911
AllCCS[M+Na]+188.032859911
AllCCS[M-H]-185.132859911
AllCCS[M+Na-2H]-187.032859911
AllCCS[M+HCOO]-189.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihomo-alpha-linolenic acidCC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O3620.0Standard polar33892256
Dihomo-alpha-linolenic acidCC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O2226.4Standard non polar33892256
Dihomo-alpha-linolenic acidCC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O2352.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihomo-alpha-linolenic acid,1TMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C2410.4Semi standard non polar33892256
Dihomo-alpha-linolenic acid,1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\CCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2655.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-alpha-linolenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-4960000000-ee31f077045fbc10d0c62017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-alpha-linolenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-022a-8972000000-11b27d7266369b9ebc182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihomo-alpha-linolenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihomo-alpha-linolenic acid LC-ESI-IT , negative-QTOFsplash10-03dr-0090000000-d8dffe611cf00f7d9e6d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 10V, Positive-QTOFsplash10-0a4r-1196000000-89a04280ae844b3d1c1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 20V, Positive-QTOFsplash10-08g1-5591000000-d0a16956780551b951782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 40V, Positive-QTOFsplash10-052g-8950000000-64dfe5d75f4f453c6c312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 10V, Negative-QTOFsplash10-0a4i-0029000000-d10c7c1b109440c211362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 20V, Negative-QTOFsplash10-0a4i-2089000000-0abcc3d67afb5981b6d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 40V, Negative-QTOFsplash10-0a4i-9130000000-fda7effe116a88cc975f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 10V, Positive-QTOFsplash10-0a4r-4596000000-995657b9029281236c8e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 20V, Positive-QTOFsplash10-0a5a-9820000000-87f7e85d00d036dc52d22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 40V, Positive-QTOFsplash10-05po-9200000000-eea6b43bb6e346821f502021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 10V, Negative-QTOFsplash10-0a4i-0019000000-a547ddaba8c204ad4b7f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 20V, Negative-QTOFsplash10-0a4r-1069000000-c4949e5e0cfdc4b33b862021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihomo-alpha-linolenic acid 40V, Negative-QTOFsplash10-0006-9210000000-30310e4351623257055d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.341 +/- 0.016 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006293
KNApSAcK IDNot Available
Chemspider ID4471954
KEGG Compound IDC16522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312529
PDB IDNot Available
ChEBI ID53460
Food Biomarker OntologyNot Available
VMH IDM00010
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.