Structure Database (LMSD)

Common Name
5(6)-Epoxy Prostaglandin E1
Systematic Name
4-(3-{[(1S,2S,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]methyl}oxiran-2-yl)butanoic acid
Synonyms
LM ID
LMFA03020068
Formula
C20H32O6
Exact Mass
Calculate m/z
368.21989
Sum Composition
FA 20:4;O4
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Leukotrienes [FA0302]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Oxo fatty acids [FA0106]
Hydroxy fatty acids [FA0105]
Epoxy fatty acids [FA0107]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Capra hircus (#9925)
Mammalia (#40674)
Metabolism of 5(6)-expoxyeicosatrienoic acid by ram seminal vesicles. Formation of novel prostaglandin E1 metabolites.,
Biochim Biophys Acta, 1984
Pubmed ID: 6538799

String Representations

InChiKey (Click to copy)
CBOBGOJUDRNUHE-HHECASJMSA-N
InChi (Click to copy)
InChI=1S/C20H32O6/c1-2-3-4-6-13(21)9-10-14-15(17(23)12-16(14)22)11-19-18(26-19)7-5-8-20(24)25/h9-10,13-16,18-19,21-22H,2-8,11-12H2,1H3,(H,24,25)/b10-9+/t13-,14-,15-,16-,18?,19?/m0/s1
SMILES (Click to copy)
C1(=O)[C@@H](CC2OC2CCCC(O)=O)[C@H](/C=C/[C@H](CCCCC)O)[C@@H](O)C1

Other Databases

KEGG ID
C04741
HMDB ID
HMDB0012110
CHEBI ID
175746
PubChem CID
53481368

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 2
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 374.66
Topological Polar Surface Area 107.36
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.61
Molar Refractivity 98.71

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Created at
-
Updated at
4th Jul 2020