PGH2   Click here for help

GtoPdb Ligand ID: 4483

Synonyms: prostaglandin H2
Compound class: Metabolite
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 75.99
Molecular weight 352.22
XLogP 4.35
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCC(C=CC1C2OOC(C1CC=CCCCC(=O)O)C2)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1[C@@H]2OO[C@H]([C@@H]1C/C=C\CCCC(=O)O)C2)O
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
InChI Key YIBNHAJFJUQSRA-YNNPMVKQSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
COX-2 1.14.99.1, 1.14.99.1 Hydrogen donor + arachidonic acid + 2O2 = hydrogen acceptor + H2O + PGH2

Arachidonic acid => PGG2 => PGH2
L-PGDS 5.3.99.2 PGH2 = PGD2
H-PGDS 5.3.99.2 PGH2 = PGD2
mPGES1 5.3.99.3 PGH2 = PGE2
CYP5A1 5.3.99.5 PGH2 = thromboxane A2
cPGES 5.3.99.3 PGH2 = PGE2
COX-1 1.14.99.1, 1.14.99.1 Hydrogen donor + arachidonic acid + 2O2 = hydrogen acceptor + H2O + PGH2

Arachidonic acid => PGG2 => PGH2
mPGES2 5.3.99.3 PGH2 = PGE2
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at TP receptor thromboxane A2 = PGH2 >> PGD2, PGE2, PGF2α, PGI2
Targets where the ligand is described in the comment field
Target Comment
CYP8A1 in CYP5, CYP7 and CYP8 families
CYP8A1 in Prostaglandin synthases
 Converts prostaglandin H2 (PGH2) to thromboxane A2 (thromboxane A2) [2].
CYP4F8 Converts PGH2 to 19-hydroxyPGH2 [1] and 8,9-EET or 11,12-EET to 18-hydroxy-8,9-EET or 18-hydroxy-11,12-EET [3].
Ligand mentioned in the following text fields
Cyclooxygenase overview
Prostaglandin synthases overview
Prostanoid receptors overview