LIPID MAPS

Structure Database (LMSD)

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Common Name

5,6-epoxyisoprostane

Systematic Name

(5R,6R)-epoxy-9-oxo-11R-hydroxy-7E,14Z-prostadienoic acid-cyclo[8,12R]

Synonyms

LM ID

LMFA03110369

Formula

C₂₀H₃₀O₅

Exact Mass

Calculate m/z

350.209326

Sum Composition

FA 20:5;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

No other lipid differing only in stereochemistry/bond geometry found

Classification

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Total synthesis of the epoxy isoprostane phospholipids PEIPC and PECPC.,
Org Lett, 2005

Pubmed ID: 16119935

DOI: 10.1021/ol051415y

String Representations

InChiKey (Click to copy)

HHCKGRLRYHXQJS-QRKAMBPMSA-N

InChi (Click to copy)

InChI=1S/C20H30O5/c1-2-3-4-5-6-7-9-14-15(17(22)13-16(14)21)12-19-18(25-19)10-8-11-20(23)24/h6-7,12,14,16,18-19,21H,2-5,8-11,13H2,1H3,(H,23,24)/b7-6-,15-12+/t14-,16-,18-,19-/m1/s1

SMILES (Click to copy)

[C@@H]1(O[C@@H]1CCCC(=O)O)/C=C1/C(=O)C[C@@H](O)[C@@H]/1C/C=C\CCCCC

Other Databases

PubChem CID

73355610

Calculated Physicochemical Properties

Heavy Atoms 25

Rings 2

Aromatic Rings

Rotatable Bonds 11

Van der Waals Molecular Volume 363.23

Topological Polar Surface Area 87.13

Hydrogen Bond Donors 2

Hydrogen Bond Acceptors 5

logP 4.27

Molar Refractivity 96.79

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Created at

21st Aug 2026

Updated at