(Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-3-methyloct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
Basic information
- CAS
210978-26-0- Standard SMILES
CCCCC[C@@](C)(O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O- InChIKey
CTXLUMAOXBULOZ-BKVRKCTKSA-N- Molecular formula
- C21H34O5
- Average molar mass
- 366.5 g/mol
- Monoisotopic mass
- 366.24062418
Overview
15-methyl-15R-PGD2 is a prostanoid.
Names & identifiers
- Preferred name
- (Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-3-methyloct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
- IUPAC
- (Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-3-methyloct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
- English name
- 15(R)-15-Methyl prostaglandin d2
- Molecular formula
- C21H34O5
- Molecular weight
- 366.49
Names & synonyms
210978-26-015(R)-15-methyl Prostaglandin D215-methyl-15R-PGD215(R)-15-methyl-PGD2(Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3R)-3-hydroxy-3-methyloct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid15R-methyl-prostaglandin D215-methyl-15R-Prostaglandin D215(R)?-?15-?Methyl prostaglandin D29S,15R-dihydroxy-11-oxo-15-methyl-5Z,13E-prostadienoic acid15(R)-15-methyl PGD215R-15-methyl PGD2GTPL1902
Show more names
CTXLUMAOXBULOZ-BKVRKCTKSA-N15(R)-15-methyl Prostaglandin D2 Exclusive9a,15R-Dihydroxy-11-oxo-15-methylprosta-5Z,13E-dien-1-oic acid9ALPHA,15R-DIHYDROXY-11-OXO-15-METHYL-PROSTA-5Z,13E-DIEN-1-OIC ACIDProsta-5,13-dien-1-oic acid, 9,15-dihydroxy-15-methyl-11-oxo-, (5Z,9α,13E,15R)-
orb1693033SCHEMBL26834196CHEBI:185064HMS3648O07LMFA03010105MFCD00216045AKOS040755720PD021334
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 12
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 511
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physicochemical properties
- storage temp.
- 20 °C · −20°C
- solubility
- 100 mg/ml; · DMF: >100 mg/ml; DMSO: >50 mg/ml; Ethanol: >75 mg/ml; PBS (pH 7.2): >5 mg/ml
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Danger
- Hazard Codes
- T
- Risk Statements
- 60 · 60-22
- Safety Statements
- 53 · 53-22-26-36
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
- risk_code
- 60-22
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07,GHS08
- hazard_code
- T
- safety_code
- 53-22-26-36
Chemistry & industry
Applications
Uses15(R)-15-Methyl prostaglandin D2 (15(R)-15-methyl PGD2) is a metabolically stable synthetic analog of PGD2. The physiological actions of PGD2 include regulation of sleep, lowering of body temperature, inhibition of platelet aggregation and relaxation of vascular smooth muscle. PGD2 mediates its effects by 2 distinct G-protein-coupled receptors, DP1and CRTH2/DP2. 15(R)-15-Methyl prostaglandin D2 is a potent, selective agonist for the CRTH2/DP2 receptor. The EC50 values for eosinophil CD11b expression, actin polymerization, and chemotaxis are 1.4, 3.8, and 1.7 nM, respectively, each of which is approximately 3-5 fold lower than those for PGD2. In contrast the EC50 for the DP1-mediated increase in platelet cAMP by 15(R)-15-methyl PGD2 is >10 μM.
Additional notes
DefinitionChEBI: 15-methyl-15R-PGD2 is a prostanoid.
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