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Structure Database (LMSD)

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Common Name

1a,1b-dihomo-PGE2

Systematic Name

1a,1b-dihomo-9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid

Synonyms

1a,1b-dihomo-Prostaglandin E2

LM ID

LMFA03010155

Formula

C₂₂H₃₆O₅

Exact Mass

Calculate m/z

380.256275

Sum Composition

FA 22:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

1a,1b-dihomo Prostaglandin E2 (1a,1b-dihomo PGE2) is a rare polyunsaturated fatty acid first identified in extracts of sheep vesicular gland microsomes, known to contain COX, incubated with adrenic acid .¹ 1a,1b-dihomo PGE2 has also been identified in conditioned media of RAW 264.7 macrophages stimulated with endotoxin and arachidonic acid (AA).² This product is thought to be produced by elongation of AA to adrenic acid, which is then metabolized sequentially by COX and PGE synthase.²

This information has been provided by Cayman Chemical

References

1. Harkewicz, R., Fahy, E., Andreyev, A., et al. Arachidonate-derived dihomoprostaglandin production observed in endotoxin-stimulated macrophage-like cells. The Journal of Biological Chemisty 282(5), 2899-2910 (2007).

2. Tobias, L.D., Vane, F.M., and Paulsrud, J.R. The biosynthesis of 1a,1b-dihomo-PGE2 and 1a,1b-dihomo-PGF2a from 7,10,13,16-docosatetraenoic acid by an acetone-pentane powder of sheep vesicular gland microsomes. Prostaglandins 10(3), 443-468 (1975).

String Representations

InChiKey (Click to copy)

PNKJEXAWAIJTRO-QKIVIXBWSA-N

InChi (Click to copy)

InChI=1S/C22H36O5/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/h6,9,14-15,17-19,21,23,25H,2-5,7-8,10-13,16H2,1H3,(H,26,27)/b9-6-,15-14+/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]1C/C=C\CCCCCC(O)=O