CHEBI:138101 - 2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine

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ChEBI Name 2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine
ChEBI ID CHEBI:138101
ChEBI ASCII Name 2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine
Definition A prostanoid-LPC that is the ammonium betaine of a 2-(prostaglandin H2)-sn-glycero-3-phosphocholine arising from deprotonation of the phosphate OH group; major species at pH 7.3.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Nevila Nouspikel
Supplier Information
Download Molfile XML SDF
Formula C28H50NO10P
Net Charge 0
Average Mass 591.672
Monoisotopic Mass 591.31723
InChI InChI=1S/C28H50NO10P/c1-5-6-9-12-22(31)15-16-25-24(26-19-27(25)39-38-26)13-10-7-8-11-14-28(32)37-23(20-30)21-36-40(33,34)35-18-17-29(2,3)4/h7,10,15-16,22-27,30-31H,5-6,8-9,11-14,17-21H2,1-4H3/b10-7-,16-15+/t22-,23+,24+,25+,26-,27+/m0/s1
InChIKey QNEYMHCJQNZTAZ-BWEJQOJRSA-N
SMILES P(=O)([O-])(OCC[N+](C)(C)C)OC[C@@H](CO)OC(CCC/C=C\C[C@H]1[C@@H]2C[C@H]([C@@H]1/C=C/[C@H](CCCCC)O)OO2)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Biological Role(s): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via lysophosphatidylcholine )
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ChEBI Ontology
Outgoing 2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine (CHEBI:138101) has functional parent prostaglandin H2 (CHEBI:15554)
2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine (CHEBI:138101) has role human xenobiotic metabolite (CHEBI:76967)
2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine (CHEBI:138101) has role mouse metabolite (CHEBI:75771)
2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine (CHEBI:138101) is a 2-acyl-sn-glycero-3-phosphocholine (CHEBI:57875)
2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine (CHEBI:138101) is a prostanoid (CHEBI:26347)
2-[(9S,11R)-epidioxy-(15S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3- phosphocholine (CHEBI:138101) is a secondary allylic alcohol (CHEBI:134396)
IUPAC Name
(2R)-3-hydroxy-2-{[(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl}hept-5-enoyl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphate
Synonyms Sources
2-(prostaglandin H2)-sn-glycero-3-phosphocholine UniProt
2-[(9S,11R)-epidioxy-15(S)-hydroxy-(5Z,13E)-prostadienoyl]-sn-glycero-3-phosphocholine SUBMITTER
Citation Waiting for Citations Type Source
27642067 PubMed citation SUBMITTER
Last Modified
23 October 2017