CAS 27415-25-4 8-Isoprostaglandin E2 (HCID 5283213)

Substructure search Find similar structures

Basic information

CAS: 27415-25-4
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
Molecular formula: C20H32O5
Average molar mass: 352.5 g/mol
Monoisotopic mass: 352.22497412

Overview

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.

Names & identifiers

Preferred 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
English name: 8-ISO prostaglandin E2
Molecular formula: C20H32O5
Molecular weight: 352.47

Names & synonyms

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

Show more names

(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

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 94.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 12
Heavy atoms: 25
Formal charge: 0
Complexity: 469

Experimental & physicochemical properties

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]

Physicochemical properties

Boiling point: 530.1 · 530.1±50.0 °C(Predicted)
Density: 1.148 · 1.148±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
solubility: 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)
form: A crystalline solid
pka: 4.75 · 4.75±0.10(Predicted)
color: White to off-white
FDA UNII: 1 ANC8Q5NW · W1ANC8Q5NW

Safety & regulation

Safety data

Signal word: Danger
Symbol(GHS): GHS07,GHS08
Hazard statements: H302-H360
Precautionary statements: P201-P202-P264-P270-P280-P301+P312-P330-P308+P313-P405-P501

Chemistry & industry

Pharmacology

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

Cellular LocationsExtracellular

Applications

Uses8-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.