LIPID MAPS

Structure Database (LMSD)

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Common Name

5,6-epoxycyclopentenone

Systematic Name

(5R,6R)-epoxy-9-oxo-7E,10,14Z-prostatrienoic acid-cyclo[8,12S]

Synonyms

LM ID

LMFA03110370

Formula

C₂₀H₂₈O₄

Exact Mass

Calculate m/z

332.198761

Sum Composition

FA 20:6;O2

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)

OLORIVCLQTVGGC-UYMWDNJASA-N

InChi (Click to copy)

InChI=1S/C20H28O4/c1-2-3-4-5-6-7-9-15-12-13-17(21)16(15)14-19-18(24-19)10-8-11-20(22)23/h6-7,12-15,18-19H,2-5,8-11H2,1H3,(H,22,23)/b7-6-,16-14+/t15-,18+,19+/m0/s1

SMILES (Click to copy)

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

Other Databases

PubChem CID

11279009

Calculated Physicochemical Properties

Heavy Atoms 24

Rings 2

Aromatic Rings

Rotatable Bonds 11

Van der Waals Molecular Volume 351.80

Topological Polar Surface Area 66.90

Hydrogen Bond Donors 1

Hydrogen Bond Acceptors 4

logP 4.79

Molar Refractivity 94.79

Admin

Created at

21st Aug 2026

Updated at