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Human Metabolome Database Version 3.5

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Showing metabocard for Dihomo-gamma-Linolenoyl ethanolamide (HMDB13625)

Record Information
Version 3.5
Creation Date 2010-05-20 04:41:07 -0600
Update Date 2013-02-08 17:30:40 -0700
HMDB ID HMDB13625
Secondary Accession Numbers None
Metabolite Identification
Common Name Dihomo-gamma-Linolenoyl ethanolamide
Description Dihomo-gamma-Linolenoyl ethanolamide is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337 Link_out, 12056855 Link_out, 12560208 Link_out, 11997249 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide
  2. 8,11,14-Eicosatrienoylethanolamide
  3. Anandamide (20.3,N-6)
  4. DGLA EA
  5. Dihomo-gamma-linolenoylethanol amide
  6. Hglea
  7. Homo-gamma-linolenylethanolamide
  8. N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide
Chemical Formula C22H39NO2
Average Molecular Weight 349.5506
Monoisotopic Molecular Weight 349.298079497
IUPAC Name (8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide
Traditional IUPAC Name hglea
CAS Registry Number 150314-34-4
SMILES CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO
InChI Identifier InChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-
InChI Key ULQWKETUACYZLI-QNEBEIHSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Amides
Sub Class N-acyl Amines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • N-(long-chain-acyl)ethanolamine(ChEBI)
  • N-acyl ethanolamides (endocannabinoids)(KEGG)
  • N-acyl ethanolamines (endocannabinoids)(Lipidmaps)
Substituents
  • Acyclic Alkene
  • Carboxamide Group
  • N Acylethanolamine
  • Primary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent N-acyl Amines
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
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
Water Solubility 2.340E-04 g/L ALOGPS
LogP 6.28 ALOGPS
LogP 5.68 ChemAxon
LogS -6.17 ALOGPS
pKa (strongest acidic) 15.45 ChemAxon
pKa (strongest basic) -0.33 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 49.33 A2 ChemAxon
Rotatable Bond Count 17 ChemAxon
Refractivity 111.85 ChemAxon
Polarizability 44.39 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
1.01 +/- 0.48 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029602
KNApSAcK ID Not Available
Chemspider ID 4445443 Link_out
KEGG Compound ID C13828 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13625 Link_out
Metagene Link HMDB13625 Link_out
METLIN ID Not Available
PubChem Compound 5282272 Link_out
PDB ID Not Available
ChEBI ID 34488 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available