Structure Database (LMSD)

Common Name
PGF2alpha-d4
Systematic Name
9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid (3,3,4,4-d4)
Synonyms
  • Prostaglandin F2alpha-d4
LM ID
LMFA03010006
Formula
C20H30D4O5
Exact Mass
Calculate m/z
358.265733
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

Biological Context

Prostaglandin F2α-d4 (PGF2α-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 PGF2α by GC- or LC-mass spectrometry. PGF2α is a widely distributed prostaglandin occurring in many species.1,2,3 It causes contraction of vascular, bronchial, intestinal, and myometrial smooth muscle, and also exerts potent luteolytic activity.1 PGF2α exhibits its receptor mediated physiological activity at 50-100 nM.1 Maximal ovine myometrial contraction can be achieved at 125 nM PGF2α in vitro.4

This information has been provided by Cayman Chemical

References

1. Crankshaw, D.J., and Gaspar, V. Pharmacological characterization in vitro of prostanoid receptors in the myometrium of nonpregnant ewes. J. Reprod. Fertil. 103(1), 55-61 (1995).
2. Watanabe, K., Iguchi, Y., Iguchi, S., et al. Stereospecific conversion of prostaglandin D2 to (5Z,13E)-(15S)-9α,-11β,15-trihydroxyprosta-5,13-dien-1-oic acid (9α,11β-prostaglandin F2) and of prostaglandin H2 to prostaglandin F2α by bovine lung prostaglandin F synthase. Proc. Natl. Acad. Sci. USA 83(6), 1583-1587 (1986).
3. Speroff, L., and Ramwell, P.W. Prostaglandins in reproductive physiology. Am. J. Obstet. Gynecol. 107(7), 1111-1130 (1970).
4. Samuelsson, B., Goldyne, M., Granström, E., et al. Prostaglandins and thromboxanes. Annu. Rev. Biochem. 47, 997-1029 (1978).

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)
PXGPLTODNUVGFL-MKIWGZNBSA-N
InChi (Click to copy)
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1/i5D2,8D2
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\C([2H])([2H])C([2H])([2H])CC(=O)O

Other Databases

PubChem CID
5283029
Cayman ID
316010

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Created at
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Updated at
29th Jan 2021