CHEBI:132908 - 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid

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ChEBI Name 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid
ChEBI ID CHEBI:132908
ChEBI ASCII Name 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid
Definition A polyunsaturated fatty acid that is (6E,8Z,11Z,14Z,16E)-icosapentaenoic acid substituted at positions 5 and 18 by hydroperoxy and hydroxy groups respectively (the 5S, 18R-stereoisomer).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H30O5
Net Charge 0
Average Mass 350.450
Monoisotopic Mass 350.20932
InChI InChI=1S/C20H30O5/c1-2-18(21)14-11-9-7-5-3-4-6-8-10-12-15-19(25-24)16-13-17-20(22)23/h3-4,7-12,14-15,18-19,21,24H,2,5-6,13,16-17H2,1H3,(H,22,23)/b4-3-,9-7-,10-8-,14-11+,15-12+/t18-,19-/m1/s1
InChIKey JIOJPWROWDJRKM-NNQKPOSRSA-N
SMILES [C@H](CCCC(O)=O)(/C=C/C=C\C/C=C\C\C=C/C=C/[C@@H](CC)O)OO
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound.
(via hydroperoxy(hydroxy)icosapentaenoic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:132908) has role human blood serum metabolite (CHEBI:85234)
5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:132908) has role human xenobiotic metabolite (CHEBI:76967)
5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:132908) is a hydroperoxy(hydroxy)icosapentaenoic acid (CHEBI:134645)
5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:132908) is conjugate acid of 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoate (CHEBI:132218)
Incoming 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoate (CHEBI:132218) is conjugate base of 5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid (CHEBI:132908)
IUPAC Name
(5S,6E,8Z,11Z,14Z,16E,18R)-5-hydroperoxy-18-hydroxyicosa-6,8,11,14,16-pentaenoic acid
Synonyms Sources
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoic acid ChEBI
(5S)-hydroperoxy-(18R)-hydroxy-(6E,8Z,11Z,14Z,16E)-icosapentaenoic acid ChEBI
18(R)-hydroxy-5(S)-HpEPE ChEBI
5(S)-Hp-18(R)-HEPE ChEBI
5(S)-hydroperoxy-18(R)-hydroxy-(6E,8Z,11Z,14Z,16E)-eicosapentaenoic acid ChEBI
Registry Number Type Source
14535272 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21206090 PubMed citation Europe PMC
Last Modified
21 February 2017