8-Isoprostaglandin E2

HCID 5283213CAS 27415-25-4

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Grundinformationen

Standard-SMILES: CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@H]1C/C=C\CCCC(=O)O
InChIKey: XEYBRNLFEZDVAW-CLQOMRTCSA-N
Summenformel: C20H32O5
Durchschnittliche Molmasse: 352,5 g/mol
Monoisotopische Masse: 352,22497412

Überblick

8-epi-prostaglandin E2 is a prostanoid that is prostaglandin E2 having inverted stereochemistry at the 8-position. It has a role as a bronchoconstrictor agent, a vasoconstrictor agent, a human metabolite and a rat metabolite. It is a diol, a prostanoid, a secondary alcohol and a cyclic ketone. It is functionally related to a prostaglandin E2.

Namen und Bezeichner

Bevorzugter Name: 8-Isoprostaglandin E2
IUPAC: (Z)-7-[(1S,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid
Englischer Name: 8-ISO prostaglandin E2
Summenformel: C20H32O5
Molmasse: 352.47

Namen und Synonyme

8-isoprostaglandin E28-Iso-PGE227415-25-4W1ANC8Q5NWDTXSID701024826Prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,8beta,11alpha,13E,15S)-9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid-cyclo(8S,12R)RefChem:107216DTXCID001509011(Z)-7-[(1S,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid8-ISOPROSTAGLANDINE2

Weitere Namen anzeigen

(8S)-PGE2)8-ISO prostaglandin E2Dinoprostone EP Impurity B8-iso Prostaglandin E2 ExclusiveAlprostadil (Prostaglandin E1) Impurity 8 (8S)-PGE2Alprostadil (prostaglandin E1) Impurity 16 (8S) -PGE29-OXO-11ALPHA,15S-DIHYDROXY-(8BETA)-PROSTA-5Z,13E-DIEN-1-OIC ACIDProsta-5,13-dien-1-oic acid, 11,15-dihydroxy-9-oxo-, (5Z,8β,11α,13E,15S)-

(Z)-7-((1S,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)hept-5-enoic acid8-epi-prostaglandin E2UNII-W1ANC8Q5NWXEYBRNLFEZDVAW-CLQOMRTCSA-N8-epi-PGE28-ISODINOPROSTONE15-E2t-IsoPProstaglandin Impurity 11

Datenbank-Bezeichner

CAS: 27415-25-4
PubChem CID: 5283213
DTXSID: DTXSID701024826
ChEBI: CHEBI:131888
UNII: W1ANC8Q5NW
Nikkaji: J838.387A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,8
Polarare Oberfläche (TPSA): 94,8 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 12
Schwere Atome: 25
Formalladung: 0
Komplexität: 469

Experimentelle und physikochemische Eigenschaften

LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Isoprostanes [FA0311]

Physical DescriptionSolid

Collision Cross Section188.6 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

Physikochemische Eigenschaften

Siedepunkt: 530.1 · 530.1±50.0 °C(Predicted)
Dichte: 1.148 · 1.148±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
Löslichkeit: 100 mg/ml · DMF: >100 mg/ml (from PGE2); DMSO: >100 mg/ml (from PGE2); Ethanol: >100 mg/ml (from PGE2); PBS pH 7.2: >5 mg/ml (from PGE2)
Aggregatzustand: A crystalline solid
pka: 4.75 · 4.75±0.10(Predicted)
Farbe: White to off-white

Sicherheit und Regulatorisches

Sicherheitsdaten

Alarmwort: Achtung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationDrugs used to cause constriction of the blood vessels.

Cellular LocationsExtracellular

Anwendungen

Verwenden8-iso Prostaglandin E2 is a Prostaglandin formed from arachidonic acid. 8-iso Prostaglandin E2 is an inhibitor of endogenous amino acid neurotransmitter levels in bovine retina.