EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:138563 - 5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid

Default Structure
ChEBI IDCHEBI:138563
ChEBI Name5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid
Stars
ASCII Name5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid
DefinitionA polyunsaturated fatty acid consisting of (7E,9E,11Z,14Z,16E)-icosapentaenoic acid carrying additional (18R)-hydroxy and (5S,6)-epoxy groups.
Last Modified27 April 2026
SubmitterBijay
DownloadsMolfile
FormulaC20H28O4
Net Charge0
Average Mass332.440
Monoisotopic Mass332.19876
SMILESCC[C@@H](O)/C=C/C=C\C/C=C\C=C\C=C\C1O[C@H]1CCCC(=O)O
InChIInChI=1S/C20H28O4/c1-2-17(21)13-10-8-6-4-3-5-7-9-11-14-18-19(24-18)15-12-16-20(22)23/h3,5-11,13-14,17-19,21H,2,4,12,15-16H2,1H3,(H,22,23)/b5-3-,8-6-,9-7+,13-10+,14-11+/t17-,18?,19+/m1/s1
InChIKeyZPAJZAMPZXISSE-RHCRZREESA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563) is a epoxy fatty acid (CHEBI:61498)
5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563) is a hydroxy polyunsaturated fatty acid (CHEBI:140345)
5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563) is a icosanoid (CHEBI:23899)
5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563) is a long-chain fatty acid (CHEBI:15904)
5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563) is conjugate acid of 5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoate (CHEBI:747604)
Incoming Relation(s)
5(S),6(S)-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:132909) is a 5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563)
5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoate (CHEBI:747604) is conjugate base of 5(S),6-epoxy-18(R)-hydroxy-(7E,9E,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:138563)
IUPAC Name 
4-{(2S)-3-[(1E,3E,5Z,8Z,10E,12R)-12-hydroxytetradeca-1,3,5,8,10-pentaen-1-yl]oxiran-2-yl}butanoic acid
Synonyms  Source
5S,6-Ep-18R-HEPEChEBI
5S,6-epoxy-18R-HEPEChEBI
5S(6)-epoxy-18R-HEPEChEBI
5S(6)-epoxy-18(R)-HEPEChEBI
5S,6-epoxy,18R-hydroxy-7E,9E,11Z,14Z,16E-eicosapentaenoic acidChEBI
Citations