Structure Database (LMSD)
Common Name
1a,1b-dihomo-PGE1
Systematic Name
9-oxo-11R,15S-dihydroxy-1a,1b-dihomo-13E-prostaenoic acid
Synonyms
- 1a,1b-dihomo-Prostaglandin E1
LM ID
LMFA03010108
Formula
Exact Mass
Calculate m/z
382.271925
Sum Composition
Status
Curated
3D model of 1a,1b-dihomo-PGE1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Prostaglandin 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
This information has been provided by Cayman Chemical
References
1. Kloeze, J. Relationship between chemical structure and platelet-aggregation activity of prostaglandins. Biochim. Biophys. Acta 187(3), 285-292 (1969).
3. Hoshi, K. Approved indications of lipo-PGE1 in Japan. Adv. Drug Deliv. Rev. 20(2-3), 171-176 (1996).
String Representations
InChiKey (Click to copy)
YMDDELUTDBQEMT-QZCLESEGSA-N
InChi (Click to copy)
InChI=1S/C22H38O5/c1-2-3-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-4-5-7-10-13-22(26)27/h14-15,17-19,21,23,25H,2-13,16H2,1H3,(H,26,27)/b15-14+/t17-,18+,19+,21+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1CCCCCCCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
1
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
412.83
Topological Polar Surface Area
94.83
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
4.83
Molar Refractivity
107.50
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Updated at
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