Structure Database (LMSD)

OH O
Common Name
EPA
Systematic Name
5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms
  • (5Z,8Z,11Z,14Z,17Z)-Icosapentaenoic acid
  • Timnodonic acid
  • C20:5n-3,6,9,12,15
LM ID
LMFA01030759
Formula
C20H30O2
Exact Mass
Calculate m/z
302.22458
Sum Composition
FA 20:5
Status
Active
Show lipids differing only in stereochemistry/bond geometry
View ion mobility data
View lipid standard

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

String Representations

InChiKey (Click to copy)
JAZBEHYOTPTENJ-JLNKQSITSA-N
InChi (Click to copy)
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
SMILES (Click to copy)
OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

Other Databases

Wikipedia
Eicosapentaenoic_acid
KEGG ID
C06428
HMDB ID
HMDB0001999
CHEBI ID
28364
PubChem CID
446284
PlantFA ID
10412
SwissLipids ID
SLM:000000409
Cayman ID
26415
PDB ID
EPA
GuidePharm ID
3362

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 356.30
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.99
Molar Refractivity 95.95

Reactions

Filter by species:
ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

Admin

Created at
-
Updated at
25th Apr 2022