LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

PGH2

Systematic Name

9S,11R-epidioxy-15S-hydroxy-5Z,13E-prostadienoic acid

Synonyms

Prostaglandin H2

LM ID

LMFA03010010

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224975

Sum Composition

FA 20:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

View ion mobility data

Classification

Biological Context

Prostaglandin H2 (PGH2) was first isolated from incubations of arachidonic acid with ovine seminal vesicle microsomes, and was described as a potent vasoconstrictor.¹ PGH2 is the precursor for all 2-series PGs and thromboxanes (TXs), and is a TP receptor agonist which irreversibly aggregates human platelets at 50-100 ng/ml.²

This information has been provided by Cayman Chemical

References

1. Samuelsson, B., Goldyne, M., Granström, E., et al. Prostaglandins and thromboxanes. Annu. Rev. Biochem. 47, 997-1029 (1978).

2. Hamberg, M., Svensson, J., Wakabayashi, T., et al. Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation. Proc. Natl. Acad. Sci. USA 71(2), 345-349 (1974).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ovis aries (#9940)

Mammalia (#40674)

Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation.,
Proc Natl Acad Sci U S A, 1974

Pubmed ID: 4521806

String Representations

InChiKey (Click to copy)

YIBNHAJFJUQSRA-YNNPMVKQSA-N

InChi (Click to copy)

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@@H]2OO[C@@H](C2)[C@@H]1C/C=C\CCCC(=O)O