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CHEBI:138565 - (5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosapentaenoic acid

ChEBI IDCHEBI:138565
ChEBI Name(5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosapentaenoic acid
Stars
ASCII Name(5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosapentaenoic acid
DefinitionA hydroperoxyicosapentaenoic acid that is (5Z,8Z,11Z,14Z,16E)-icosapentaenoic acid in which the pro-R hydrogen at position 18 has been replaced by a hydroperoxy group. One of the two stereoisomers formed when acetylated COX2 oxidises the ω-3 fatty acid EPA.
Last Modified6 December 2017
SubmitterBijay
DownloadsMolfile
FormulaC20H30O4
Net Charge0
Average Mass334.456
Monoisotopic Mass334.21441
SMILESCC[C@H](/C=C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)OO
InChIInChI=1S/C20H30O4/c1-2-19(24-23)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(21)22/h4-7,10-13,15,17,19,23H,2-3,8-9,14,16,18H2,1H3,(H,21,22)/b6-4-,7-5-,12-10-,13-11-,17-15+/t19-/m1/s1
InChIKeyZNUBMQUXCKZUTC-UAAZXLHOSA-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)
(5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosapentaenoic acid (CHEBI:138565) has functional parent all-cis-5,8,11,14,17-icosapentaenoic acid (CHEBI:28364)
(5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosapentaenoic acid (CHEBI:138565) is a hydroperoxyicosapentaenoic acid (CHEBI:138392)
IUPAC Names 
(5Z,8Z,11Z,14Z,16E,18R)-18-hydroperoxyicosa-5,8,11,14,16-pentaenoic acid
(18R)-HpEPE
18(R)-HpEPE
Registry NumbersSources
Reaxys:14535261Reaxys