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Structure Database (LMSD)

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Common Name

6k-PGF1alpha-d4

Systematic Name

9S,11R,15S-trihydroxy-6-oxo-13E-prostenoic acid (3,3,4,4-d4)

Synonyms

6k-Prostaglandin F1alpha-d4

LM ID

LMFA03010037

Formula

C₂₀H₃₀D₄O₆

Exact Mass

Calculate m/z

374.260648

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

6-keto Prostaglandin F1α-d4 (6-keto PGF1α-d4) contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of 6-keto PGF1α by GC- or LC-MS. 6-keto PGF1α is the inactive, non-enzymatic hydrolysis product of PGI2.1,2 6-keto PGF1α serves as a useful marker of PGI2 biosynthesis in vivo.³ When [3H]-PGI2 is injected into healthy human males, 6.6% of the radioactivity is recovered from urine as [3H]-6-keto PGF1α.³

This information has been provided by Cayman Chemical

References

1. Brash, A.R., Jackson, E.K., Saggese, C.A., et al. Metabolic disposition of prostacyclin in humans. J. Pharmacol. Exp. Ther. 226(1), 78-87 (1983).

2. Pace-Asciak, C.R. Isolation, structure, and biosynthesis of 6-ketoprostaglandin F1α in the rat stomach. J. Am. Chem. Soc. 98(8), 2348-2349 (1976).

3. Johnson, R.A., Morton, D.R., Kinner, J.H., et al. The chemical structure of prostaglandin X (prostacyclin). Prostaglandins 12(6), 915-928 (1976).

References

Comments

Synthetic deuterated standard

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

KFGOFTHODYBSGM-GKZGVFJGSA-N

InChi (Click to copy)

InChI=1S/C20H34O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h10-11,14,16-19,21,23-24H,2-9,12-13H2,1H3,(H,25,26)/b11-10+/t14-,16+,17+,18+,19-/m0/s1/i5D2,6D2

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1CC(=O)CC([2H])([2H])C([2H])([2H])CC(=O)O