8-epi-prostaglandin E2 (CHEBI:131888)

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CHEBI:131888 - 8-epi-prostaglandin E₂

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ChEBI ID	CHEBI:131888
ChEBI Name	8-epi-prostaglandin E₂
Stars
ASCII Name	8-epi-prostaglandin E2
Definition	A prostanoid that is prostaglandin E₂ having inverted stereochemistry at the 8-position.
Last Modified	6 December 2016
Submitter	mwilliams
Downloads	Molfile

Formula	C20H32O5
Net Charge	0
Average Mass	352.471
Monoisotopic Mass	352.22497
SMILES	CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@H]1C/C=C\CCCC(=O)O
InChI	InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,19+/m0/s1
InChIKey	XEYBRNLFEZDVAW-CLQOMRTCSA-N

Species of Metabolite	Component	Source	Comments
Rattus norvegicus (ncbitaxon:10116)
	-	PubMed (26654758)
	-	MetaboLights (MTBLS278)
Homo sapiens (ncbitaxon:9606)	-	PubMed (12869634)

Roles Classification

Biological Roles:	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). rat metabolite Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
Applications:	vasoconstrictor agent Drug used to cause constriction of the blood vessels. bronchoconstrictor agent A drug which causes a narrowing of the lumen of a bronchus or bronchiole.

ChEBI Ontology

Outgoing Relation(s)
	8-epi-prostaglandin E₂ (CHEBI:131888) has functional parent prostaglandin E₂ (CHEBI:15551)
	8-epi-prostaglandin E₂ (CHEBI:131888) has role bronchoconstrictor agent (CHEBI:50141)
	8-epi-prostaglandin E₂ (CHEBI:131888) has role human metabolite (CHEBI:77746)
	8-epi-prostaglandin E₂ (CHEBI:131888) has role rat metabolite (CHEBI:86264)
	8-epi-prostaglandin E₂ (CHEBI:131888) has role vasoconstrictor agent (CHEBI:50514)
	8-epi-prostaglandin E₂ (CHEBI:131888) is a cyclic ketone (CHEBI:3992)
	8-epi-prostaglandin E₂ (CHEBI:131888) is a diol (CHEBI:23824)
	8-epi-prostaglandin E₂ (CHEBI:131888) is a prostanoid (CHEBI:26347)
	8-epi-prostaglandin E₂ (CHEBI:131888) is a secondary alcohol (CHEBI:35681)

IUPAC Name
(5Z,8β,11α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid

Synonyms	Source
8-iso-PGE₂	ChEBI
8-isoprostaglandin E₂	ChEBI
8-epi-PGE₂	ChEBI
7-[3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid	HMDB

Manual Xrefs	Databases
4446334	ChemSpider
LMFA03110003	LIPID MAPS
HMDB0005844	HMDB

Registry Numbers	Sources
Reaxys:4709355	Reaxys
CAS:27415-25-4	ChemIDplus

Citations