CHEBI:133991 - (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate

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ChEBI Name (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate ChEBI ID CHEBI:133991 ChEBI ASCII Name (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate Definition A hydroperoxyoctadecatrienoate that is the conjugate base of (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoic acid, obtained by deprotonation of the carboxy group. Major microspecies at pH 7.3. Stars This entity has been manually annotated by the ChEBI Team. Submitter Anne Morgat Supplier Information No supplier information found for this compound. Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C18H29O6 Net Charge -1 Average Mass 341.420 Monoisotopic Mass 341.19696 InChI InChI=1S/C18H30O6/c1-2-16(23-21)12-8-6-7-10-14-17(24-22)13-9-4-3-5-11-15-18(19)20/h6-8,10,12,14,16-17,21-22H,2-5,9,11,13,15H2,1H3,(H,19,20)/p-1/b7-6-,12-8+,14-10+/t16-,17-/m0/s1 InChIKey MFVHQYMRUDEPIO-NYOLHIHQSA-M SMILES C(CCCCCCC[C@@H](/C=C/C=C\C=C\[C@H](CC)OO)OO)([O-])=O ChEBI Ontology Outgoing (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate (CHEBI:133991) is a hydroperoxyoctadecatrienoate (CHEBI:133558) (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate (CHEBI:133991) is conjugate base of (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoic acid (CHEBI:133990) Incoming (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoic acid (CHEBI:133990) is conjugate acid of (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadecatrienoate (CHEBI:133991) IUPAC Name (9S,10E,12Z,14E,16S)-9,16-bis(hydroperoxy)octadeca-10,12,14-trienoate Synonyms Sources (10E,12Z,14E)-(9S,16S)-9,16-dihydroperoxyoctadeca-10,12,14-trienoate SUBMITTER (9S,16S)-dihydroperoxy-(10E,12Z,14E)-octadecatrienoate UniProt 9S,16S-DiHPOTrE(1−) SUBMITTER Citation Wennman A, Jernerén F, Magnuson A, Oliw EH (2015) Expression and characterization of manganese lipoxygenase of the rice blast fungus reveals prominent sequential lipoxygenation of α-linolenic acid. Archives of biochemistry and biophysics 583, 87-95 (Source: SUBMITTER) [PubMed:26264916] [show Abstract] Magnaporthe oryzae causes rice blast disease and has become a model organism of fungal infections. M. oryzae can oxygenate fatty acids by 7,8-linoleate diol synthase, 10R-dioxygenase-epoxy alcohol synthase, and by a putative manganese lipoxygenase (Mo-MnLOX). The latter two are transcribed during infection. The open reading frame of Mo-MnLOX was deduced from genome and cDNA analysis. Recombinant Mo-MnLOX was expressed in Pichia pastoris and purified to homogeneity. The enzyme contained protein-bound Mn and oxidized 18:2n-6 and 18:3n-3 to 9S-, 11-, and 13R-hydroperoxy metabolites by suprafacial hydrogen abstraction and oxygenation. The 11-hydroperoxides were subject to β-fragmentation with formation of 9S- and 13R-hydroperoxy fatty acids. Oxygen consumption indicated apparent kcat values of 2.8 s(-1) (18:2n-6) and 3.9 s(-1) (18:3n-3), and UV analysis yielded apparent Km values of 8 and 12 μM, respectively, for biosynthesis of cis-trans conjugated metabolites. 9S-Hydroperoxy-10E,12Z,15Z-octadecatrienoic acid was rapidly further oxidized to a triene, 9S,16S-dihydroperoxy-10E,12Z,14E-octadecatrienoic acid. In conclusion, we have expressed, purified and characterized a new MnLOX from M. oryzae. The pathogen likely secretes Mo-MnLOX and phospholipases to generate oxylipins and to oxidize lipid membranes of rice cells and the cuticle. Last Modified 17 February 2022