LIPID MAPS

Structure Database (LMSD)

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Common Name

1a,1b-dihomo-PGF2alpha

Systematic Name

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

Synonyms

1a,1b-dihomo-Prostaglandin F2alpha
(11S,13R,17S)-17-F2-dihomo-IsoP[10R,14R]
10-epi-17-F2t-dihomo-IsoP

LM ID

LMFA03010157

Formula

C₂₂H₃₈O₅

Exact Mass

Calculate m/z

382.271925

Sum Composition

FA 22:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

1a,1b-dihomo Prostaglandin F2α (1a,1b-dihomo PGF2α) is the theoretical product of adrenic acid in the COX pathway.^1,2 1a,1b-dihomo PGF2α is primarily produced in renal medulla where adrenic acid is selectively distributed.²

This information has been provided by Cayman Chemical

References

1. Sprecher, H., VanRollins, M., Sun, F., et al. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. The Journal of Biological Chemisty 257(7), 3912-3918 (1982).

2. Ferretti, A., and Flanagan, V.P. Mass spectrometric evidence for the conversion of exogenous adrenate to dihomo-prostaglandins by seminal vesicle cyclo-oxygenase. A comparative study of two animal species. J. Chromatogr. 383(2), 241-250 (1986).

String Representations

InChiKey (Click to copy)

ZCTAOAWRUXSOQF-GWSKAPOCSA-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/h6,9,14-15,17-21,23-25H,2-5,7-8,10-13,16H2,1H3,(H,26,27)/b9-6-,15-14+/t17-,18+,19+,20-,21+/m0/s1

SMILES (Click to copy)

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