16,16-Dimethyl-PGA2
Basic information
- CAS
41691-92-3- Standard SMILES
CCCCC(C)(C)[C@H](O)/C=C/[C@H]1C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O- InChIKey
MOTPSJUHMGPRFZ-QEJIITRLSA-N- Molecular formula
- C22H34O4
- Average molar mass
- 362.5 g/mol
- Monoisotopic mass
- 362.24570956
Overview
16,16-dimethyl-PGA2 is a prostanoid.
Names & identifiers
- Preferred name
- 16,16-Dimethyl-PGA2
- IUPAC
- (Z)-7-[(1R,2S)-2-[(E,3R)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
- English name
- 16,16-Dimethyl prostaglandin A2
- Molecular formula
- C22H34O4
- Molecular weight
- 362.5
Names & synonyms
41691-92-316,16-dimethyl-PGA216,16-Dimethylprostagladin A2C181YIS8NPUNII-C181YIS8NP16,16-dimethyl-Prostaglandin A2(5Z,13E,15R)-15-Hydroxy-16,16-dimethyl-9-oxoprosta-5,10,13-trien-1-oic acidProsta-5,10,13-trien-1-oic acid, 15-hydroxy-16,16-dimethyl-9-oxo-, (5Z,13E,15R)-9oxo-15R-hydroxy-16,16-dimethyl-5Z,10Z,13E-prostatrienoic acidRefChem:19714916,16-dimethyl PGA216,16-dimethyl Prostaglandin A2
Show more names
MOTPSJUHMGPRFZ-QEJIITRLSA-N9-OXO-15R-HYDROXY-16,16-DIMETHYL-PROSTA-5Z,10,13E-TRIEN-1-OIC ACID
(Z)-7-[(1R,2S)-2-[(E,3R)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acidLMFA03010086orb1694089SCHEMBL5700545CHEBI:178528HMS3648K07Prosta-5,10,13-trien-1-oicacid, 15-hydroxy-16,16-dimethyl-9-oxo-, (5Z,13E,15R)- (9CI)MFCD00065727
Database identifiers
- CAS
41691-92-3
Properties
Computed structural properties
- XLogP
- 4.4
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 12
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 542
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physicochemical properties
- Boiling point
- 526.9 · 526.9±50.0 °C(Predicted)
- Density
- 1.078 · 1.078±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 75 mg/ml · DMF: >75 mg/ml (from PGA1); DMSO: >50 mg/ml (from PGA1); Ethanol: >100 mg/ml (from PGA1); PBS pH 7.2: >2.4 mg/ml (from PGA1)
- pka
- 4.75 · 4.75±0.10(Predicted)
- FDA UNII
- 181 YIS8NP · C181YIS8NP
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H302-H319-H336
- Precautionary statements
- 210 · P210-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312-P330-P303+P361+P353-P304+P340-P305+P351+P338-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-H302-H319-H336
- Precautionary statements
- P210-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312-P330-P303+P361+P353-P304+P340-P305+P351+P338-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Chemistry & industry
Applications
Description16,16-dimethyl PGA2 is a metabolism-resistant analog of PGA2 with a prolonged in vivo half-life. It inhibits the proliferation of Sendai virus in cultured African green monkey kidney cells by >90% at a concentration of 4 μg/ml. Daily infusion of 10 μg of 16,16-dimethyl PGA2 methyl ester into mice infected with influenza A virus increased survival by 40%. Similar treatment of mice inoculated with erythroleukemia cells delayed tumor growth and increased survival time.
Uses16,16-dimethyl Prostaglandin A2 is a PGA2 analog studied for its antiproliferative properties.
Additional notes
DefinitionChEBI: 16,16-dimethyl-PGA2 is a prostanoid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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