13,14-Dihydro-15-keto-pgd2
Basic information
- CAS
59894-07-4- Standard SMILES
CCCCCC(=O)CC[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O- InChIKey
VSRXYLYXIXYEST-KZTWKYQFSA-N- Molecular formula
- C20H32O5
- Average molar mass
- 352.5 g/mol
- Monoisotopic mass
- 352.22497412
Overview
13,14-dihydro-15-ketoprostaglandin D2 is a prostaglandin D that is prostaglandin D2 with a keto substituent replacing a hydroxy at position 15. It has a role as a metabolite. It is functionally related to a prostaglandin D2.
Names & identifiers
- Preferred name
- 13,14-Dihydro-15-keto-pgd2
- IUPAC
- (Z)-7-[(1R,2R,5S)-5-hydroxy-3-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid
- English name
- 13,14-Dihydro-15-keto prostaglandin d2
- Molecular formula
- C20H32O5
- Molecular weight
- 352.47
Names & synonyms
13,14-Dihydro-15-keto-pgd259894-07-413,14-Dihydro-15-ketoprostaglandin D213,14-Dihydro-15-keto-prostaglandin D2(Z)-7-[(1R,2R,5S)-5-hydroxy-3-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid11,15-dioxo-9S-hydroxy-5Z-prostenoic acidULX4SW2MF7Prost-5-en-1-oic acid, 9-hydroxy-11,15-dioxo-, (5Z,9alpha)-(Z)-7-((1R,2R,5S)-5-hydroxy-3-oxo-2-(3-oxooctyl)cyclopentyl)hept-5-enoic acidRefChem:7836713,14-DIHYDRO-15-KETO PROSTAGLANDIN D2MFCD00885499
Show more names
13,14-Dihydro-15-ketoprostadlandin D213,14-dihydro-15-keto Prostaglandin D9ALPHA-HYDROXY-11,15-DIOXO-PROST-5Z-EN-1-OIC ACID(5Z,9α)-9-Hydroxy-11,15-dioxoprost-5-en-1-oic acid13,14-dihydro-15-keto Prostaglandin D2 MaxSpecStandardProst-5-en-1-oic acid, 9-hydroxy-11,15-dioxo-, (5Z,9α)-
15-Oxo-13,14-dihydro-PGD2(5Z,9alpha)-9-Hydroxy-11,15-dioxoprost-5-en-1-oic acid13,14-dihydro-15-keto Prostaglandin D2 Lipid Maps(R) MS StandardDK-PGD213,14-dihydro-15-oxo PGD2DTXSID901357883DhkPGD2LMFA03010022
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 91.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 13
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 469
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Collision Cross Section186.8 Ų [M-H2O-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]
Physicochemical properties
- Boiling point
- 542.1 · 542.1±40.0 °C(Predicted)
- Density
- 1.086 · 1.086±0.06 g/cm3(Predicted)
- solubility
- 50 mg/mlDMSO: · DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 2.5 mg/ml
- pka
- 4.76 · 4.76±0.10(Predicted)
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319-H336
- Precautionary statements
- 210 · P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Hazard statements
- H225-H319-H336
- Precautionary statements
- P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
Description13,14-dihydro-15-keto Prostaglandin D2 (13,14-dihydro-15-keto PGD2) is a metabolite of PGD2 which is formed through the 15-hydroxy PGDH pathway. 13,14-dihydro-15-keto PGD2 was recently identified as a selective agonist for the CRTH2/DP2 receptor. It also inhibits ion flux in a canine colonic mucosa preparation. In humans, 13,14-dihydro-15-keto PGD2 is further metabolized to give 11β-hydroxy compounds which have also undergone β-oxidation of one or both side chains. Virtually no 13,14-dihydro-15-keto PGD2 survives intact in the urine.
Uses13,14-Dihydro-15-keto-PGD2 is a metabolite of Prostaglandin D2 (CAT# P838575) and a selective CRTh2/DP2 receptor agonist. CRTh2/DP2 receptors play crucial roles in atopic dermatitis, asthma, and other inflammatory diseases.
Additional notes
DefinitionChEBI: 13,14-dihydro-15-ketoprostaglandin D2 is a prostaglandins D. It has a role as a metabolite. It is functionally related to a prostaglandin D2.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
3 records
Compound notes
Loading…