CHEBI:140263 - 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid

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ChEBI Name 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid
ChEBI ID CHEBI:140263
ChEBI ASCII Name 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid
Definition A docosanoid that is 17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid in which a cysteinylglycinyl group is attached at position 16S via a sulfide linkage. An intermediate of specialized proresolving mediators
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Supplier Information
Download Molfile XML SDF
Formula C27H40N2O6S
Net Charge 0
Average Mass 520.683
Monoisotopic Mass 520.26071
InChI InChI=1S/C27H40N2O6S/c1-2-3-14-17-23(30)24(36-21-22(28)27(35)29-20-26(33)34)18-15-12-10-8-6-4-5-7-9-11-13-16-19-25(31)32/h3,5-8,10-15,18,22-24,30H,2,4,9,16-17,19-21,28H2,1H3,(H,29,35)(H,31,32)(H,33,34)/b7-5-,8-6?,12-10?,13-11-,14-3-,18-15?/t22-,23+,24-/m0/s1
InChIKey WUKLNYKELYBPSU-XFTLILIKSA-N
SMILES C(\CC=CC=CC=C[C@@H]([C@@H](C/C=C\CC)O)SC[C@H](N)C(=O)NCC(=O)O)=C\C/C=C\CCC(O)=O
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 )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): specialised pro-resolving mediator
A class of cell signaling molecules enzymatically derived from n-3 long chain polyunsaturated fatty acids that have important roles in orchestrating the resolution of tissue inflammation.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
Application(s): specialised pro-resolving mediator
A class of cell signaling molecules enzymatically derived from n-3 long chain polyunsaturated fatty acids that have important roles in orchestrating the resolution of tissue inflammation.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) has role human xenobiotic metabolite (CHEBI:76967)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) has role specialised pro-resolving mediator (CHEBI:140399)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) is a dicarboxylic acid (CHEBI:35692)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) is a dipeptide (CHEBI:46761)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) is a docosanoid (CHEBI:131863)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) is a organic sulfide (CHEBI:16385)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) is a secondary alcohol (CHEBI:35681)
16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263) is conjugate acid of 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoate(1−) (CHEBI:140397)
Incoming 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoate(1−) (CHEBI:140397) is conjugate base of 16(S)-glycinylcystein-S-yl-17(R)-hydroxy-(4Z,7Z,10,12,14,19Z)-docosahexaenoic acid (CHEBI:140263)
IUPAC Name
S-[(3Z,6R,7S,15Z,18Z)-21-carboxy-6-hydroxyhenicosa-3,8,10,12,15,18-hexaen-7-yl]-L-cysteinylglycine
Synonyms Sources
16-cysteinylglycinyl,17-hydroxy-4Z,7Z,10,12,14,19Z-docosahexaenoic acid ChEBI
PCTR2 SUBMITTER
protectin conjugate in tissue regeneration 2 SUBMITTER
Citation Waiting for Citations Type Source
25713027 PubMed citation Europe PMC
Last Modified
12 March 2018