13,14-dihydro-15-keto-PGE2

HCID 5280711CAS 363-23-5

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Grundinformationen

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

Namen und Bezeichner

Bevorzugter Name: 13,14-dihydro-15-keto-PGE2
IUPAC: (Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
Englischer Name: 13,14-DIHYDRO-15-KETO PROSTAGLANDIN E2
Summenformel: C20H32O5
Molmasse: 352.47

Namen und Synonyme

363-23-513,14-Dihydro-15-keto-PGE2PGEM15-Keto-13,14-dihydro-PGE215-keto-13,14-dihydroprostaglandin E2KH(2)PGE(2)9,15-dioxo-11R-hydroxy-5Z-prostenoic acidPGEM (13,14-dihydro-15-keto-PGE2)RefChem:437486prost-5-en-1-oic acid, 11-hydroxy-9,15-dioxo-, (5Z,11 alpha)-13,14-dihydro-15-keto Prostaglandin E213,14-Dihydro-15-ketoprostaglandin E2

Weitere Namen anzeigen

CUJMXIQZWPZMNQ-XYYGWQPLSA-N15-keto-13,14-dihydroprostaglandine213,14-Dihydro-15-ketoprostaglandinE2 solution9,15-DIOXO-11ALPHA-HYDROXY-PROST-5Z-EN-1-OIC ACID(5Z)-11α-Hydroxy-9,15-dioxoprosta-5-ene-1-oic acid(5Z,11α)-11-Hydroxy-9,15-dioxoprost-5-en-1-oic acid

13,14-dihydro-15-oxo-prostaglandin E213,14-Dihydro-15-ketoPGE2(Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid13,14-dihydro-15-keto-Prostaglandin E2PGE2 13,14-dihydroProstaglandin EM(Z)-7-((1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl)hept-5-enoic acidDTXSID30869647

Datenbank-Bezeichner

CAS: 363-23-5
PubChem CID: 5280711
DTXSID: DTXSID30869647
ChEBI: CHEBI:15550
EC Number: 633-709-4
Nikkaji: J264.983G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,4
Polarare Oberfläche (TPSA): 91,7 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 13
Schwere Atome: 25
Formalladung: 0
Komplexität: 469

Experimentelle und physikochemische Eigenschaften

Physical DescriptionSolid

Collision Cross Section184.9 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

Physikochemische Eigenschaften

Siedepunkt: 538.1 · 538.1±45.0 °C(Predicted)
Dichte: 1.086 · 1.086±0.06 g/cm3(Predicted)
storage temp.: 20 °C · −20°C
Löslichkeit: 100 mg/mlDMSO: · DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): >5 mg/ml
Aggregatzustand: Liquid
pka: 4.75 · 4.75±0.10(Predicted)
Farbe: Colorless to light yellow

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Acute Tox. 4 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；Acute Tox. 4 (100%)；STOT SE 3 (100%)

Sicherheitsdaten

wgk: 3
ridadr: UN 1231 3/PG 2
risk_code: 11-20/21/22-36/37/38-67-66-36
hazard_code: F,Xn,Xi
safety_code: 16-26-36

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular；Membrane

Anwendungen · 2 Einträge

Beschreibung13,14-dihydro-15-keto Prostaglandin E2 (13,14-dihydro-15-keto PGE2) is a metabolite of PGE2 and the primary PGE2 metabolite in plasma. It is formed from PGE2 via a 15-keto PGE2 intermediate by 15-oxo-PG Δ13 reductase. Unlike PGE2, 13,14-dihydro-15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 12 and 57 μM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = >18 and >38 μM, respectively). Levels of 13,14-dihydro-15-keto PGE2 are increased in the plasma of women in the third trimester of pregnancy and in women during and immediately after labor and delivery. Levels of 13,14-dihydro-15-keto PGE2 levels are decreased in tumor tissue compared to adjacent non-cancerous tissue isolated from patients with non-small cell lung cancer (NSCLC).

Verwenden13,14-Dihydro-15-ketoPGE2 is a primary metabolite of PGE2 in plasma.