9-oxo-11R,15S-dihydroxy-1a,1b-dihomo-13E-prostaenoic acid
Basic information
- CAS
23452-98-4- Standard SMILES
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCCCC(=O)O- InChIKey
YMDDELUTDBQEMT-QZCLESEGSA-N- Molecular formula
- C22H38O5
- Average molar mass
- 382.5 g/mol
- Monoisotopic mass
- 382.27192431
Overview
1a,1b-dihomo-PGE1 is a prostanoid.
Names & identifiers
- Preferred name
- 9-oxo-11R,15S-dihydroxy-1a,1b-dihomo-13E-prostaenoic acid
- IUPAC
- 9-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]nonanoic acid
- English name
- 1A,1B-DIHOMO PROSTAGLANDIN E1
- Molecular formula
- C22H38O5
- Molecular weight
- 382.53
Names & synonyms
1a,1b-dihomo Prostaglandin E123452-98-41a,1b-dihomo-PGE19-oxo-11R,15S-dihydroxy-1a,1b-dihomo-13E-prostaenoic acid9-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]nonanoic acid1a,1b-dihomo-Prostaglandin E11a,1b-dihomo PGE1; 9-oxo-11|A,15S-dihydroxy-1a,1b-dihomo-prost-13E-en-1-oic acidLMFA030101081a,1b-dihomo PGE11a,1b-Dihomoprostaglandin E1.alpha.-Dihomoprostaglandin E1orb1693932
Show more names
9-oxo-11α,15S-dihydroxy-1a,1b-dihomo-prost-13E-en-1-oic acid9-OXO-11ALPHA,15S-DIHYDROXY-1A,1B-DIHOMO-PROST-13E-EN-1-OIC ACIDCyclopentanenonanoic acid, 3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-, [1R-[1α,2β(1E,3S*),3α]]- (9CI)
CHEBI:184175YMDDELUTDBQEMT-QZCLESEGSA-NDTXSID701347931HMS3648A20AKOS040755129DA-59909PD021260HY-137584
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 15
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 460
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Eicosanoids [FA03] -> Prostaglandins [FA0301]
Physicochemical properties
- Boiling point
- 550.1 · 550.1±50.0 °C(Predicted)
- Density
- 1.104 · 1.104±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 100 mg/ml; · DMF: >100 mg/ml; DMSO: >50 mg/ml; Ethanol: >50 mg/ml; PBS pH 7.2: >1.6 mg/ml
- pka
- 4.78 · 4.78±0.10(Predicted)
- form
- Liquid
- color
- Colorless to light yellow
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319-H361-H336
- Precautionary statements
- 201 · P201-P202-P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-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,GHS08
- Hazard statements
- H225-H319-H361-H336
- Precautionary statements
- P201-P202-P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Chemistry & industry
Applications
DescriptionProstaglandin E1 (PGE1) is not a major naturally occurring PG, but is widely administered clinically for several indications including peripheral occlusive vascular disease, erectile dysfunction, and in neonatal cardiology.1,2 COX metabolism of the unusual fatty acid 10,13,16-docosatrienoic acid yields 1a,1b-dihomo PGE1. This rare metabolite has been recovered from incubations of whole sheep seminal vesicles, but has not been reported in humans.3 In ex vivo preparations of rat aorta and rat PRP, 1a,1b-dihomo PGE1 was found to be much less active than PGE1 itself.4
Uses1a,1b-Dihomo prostaglandin E1 (1a,1b-Dihomo PGE1) is a class of prostaglandin compound[1].
Additional notes
DefinitionChEBI: 1a,1b-dihomo-PGE1 is a prostanoid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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