CHEBI:137580 - 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion
ChEBI ID CHEBI:137580
ChEBI ASCII Name 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion
Definition A 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion obtained by transfer of a proton from the phosphate to the amino group of 2-(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl-sn-glycero-3-phosphoethanolamine; major species at pH 7.3.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Nevila Nouspikel
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C25H44NO8P
Net Charge 0
Average Mass 517.593
Monoisotopic Mass 517.28045
InChI InChI=1S/C25H44NO8P/c1-2-3-4-5-7-10-13-16-23(28)17-14-11-8-6-9-12-15-18-25(29)34-24(21-27)22-33-35(30,31)32-20-19-26/h6-7,9-11,13-14,16,23-24,27-28H,2-5,8,12,15,17-22,26H2,1H3,(H,30,31)/b9-6-,10-7-,14-11-,16-13+/t23-,24+/m0/s1
InChIKey YYNINOSNLIMLAJ-XQSHPIDZSA-N
SMILES O=C(O[C@H](CO)COP(=O)([O-])OCC[NH3+])CCC/C=C\C/C=C\C[C@H](/C=C/C=C\CCCCC)O
ChEBI Ontology
Outgoing 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:137580) is a 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:65213)
2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:137580) is a oxidized 2-acyl-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:167121)
2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:137580) is tautomer of 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine (CHEBI:138339)
Incoming 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine (CHEBI:138339) is tautomer of 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-icosatetraenoyl]-sn-glycero-3-phosphoethanolamine zwitterion (CHEBI:137580)
IUPAC Name
2-azaniumylethyl (2R)-3-hydroxy-2-{[(5Z,8Z,11R,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoyl]oxy}propyl phosphate
Synonyms Sources
2-(11R)-HETE-LPE zwitterion SUBMITTER
2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphoethanolamine UniProt
Citation
Liu X, Moon SH, Jenkins CM, Sims HF, Gross RW (2016)
Cyclooxygenase-2 Mediated Oxidation of 2-Arachidonoyl-Lysophospholipids Identifies Unknown Lipid Signaling Pathways.
Cell chemical biology 23, 1217-1227 (Source: SUBMITTER) [PubMed:27642067]
[show Abstract]
Last Modified
30 August 2017