Prostaglandin H2

Prostaglandin H2

Identifiers
CAS Number	42935-17-1
ChEBI	CHEBI:15554
ChemSpider	392800
IUPHAR/BPS	4483
Jmol 3D model	Interactive image
MeSH	Prostaglandin+H2
PubChem	445049
InChI 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 Key: YIBNHAJFJUQSRA-YNNPMVKQSA-N InChI=1/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 Key: YIBNHAJFJUQSRA-YNNPMVKQBN
SMILES O=C(O)CCC/C=C\C[C@H]2[C@H]1OO[C@H](C1)[C@@H]2/C=C/[C@@H](O)CCCCC
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Prostaglandin H2 is a type of prostaglandin and a precursor for many other biologically significant molecules. It is synthesized from arachidonic acid in a reaction catalyzed by a cyclooxygenase enzyme.^[1]

Eicosanoid synthesis - prostaglandin H2 near center

It is acted upon by:

• Prostacyclin synthase to create prostacyclin
• Thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid)
• Prostaglandin D2 synthase to create prostaglandin D2
• Prostaglandin E synthase to create prostaglandin E2

It rearranges non-enzymatically to:

• A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid)

Figure 1: Synthetic pathways from PGH₂ (the parent compound) to prostaglandins, prostacyclin and thromboxanes

References

1. "The Cyclooxygenase Reaction Mechanism". ACS Publications. Retrieved 18 April 2016.