thromboxane A2   Click here for help

GtoPdb Ligand ID: 4482

Abbreviated name: TXA2
Compound class: Metabolite
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View more information in the IUPHAR Pharmacology Education Project: thromboxane a2

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 CDK toolkit. 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 4.24
No. Lipinski's rules broken 1
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.

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Canonical SMILES CCCCCC(C=CC1OC2CC(C1CC=CCCCC(=O)O)O2)O
Isomeric SMILES CCCCC[C@@H](/C=C/[C@H]1O[C@H]2C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O2)O
InChI InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1
InChI Key DSNBHJFQCNUKMA-SCKDECHMSA-N
Natural/Endogenous Targets
Target
TP receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
CYP5A1 5.3.99.5 PGH2 = thromboxane A2
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at DP1 receptor PGD2 > PGE1 >> PGE2 > PGF2α > PGI2, thromboxane A2
Potency order of endogenous ligands at FP receptor PGF2α > PGD2 > PGE2 > PGI2, thromboxane A2
Potency order of endogenous ligands at EP4 receptor PGE2 = PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at DP2 receptor PGD2 >> PGF2α, PGE2 > PGI2, thromboxane A2
Potency order of endogenous ligands at TP receptor thromboxane A2 = PGH2 >> PGD2, PGE2, PGF2α, PGI2
Potency order of endogenous ligands at EP2 receptor PGE2 = PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at EP1 receptor PGE2 > PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at EP3 receptor PGE2, PGE1 > PGF2α, PGI2 > PGD2, thromboxane A2
Potency order of endogenous ligands at IP receptor PGI2 >> PGE1 > PGD2, PGF2α > thromboxane A2
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) [1].
Ligand mentioned in the following text fields
Prostaglandin synthases overview
Prostanoid receptors overview