atecegatran metoxil   Click here for help

GtoPdb Ligand ID: 7682

Synonyms: atecegatran fexenetil | AZD 0837 | AZD-0837 | AZD0837
Compound class: Synthetic organic
Comment: This direct thrombin inhibitor prodrug (aka AZD0837) from AstraZeneca was the follow-up for AZ3971. It is dicussed in the recent AZ 2014 review paper [1].
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 6
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 126.48
Molecular weight 496.13
XLogP 2.82
No. Lipinski's rules broken 0
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 CON=C(c1ccc(cc1)CNC(=O)C1CCN1C(=O)C(c1cc(Cl)cc(c1)OC(F)F)O)N
Isomeric SMILES CO/N=C(/c1ccc(cc1)CNC(=O)[C@@H]1CCN1C(=O)[C@@H](c1cc(Cl)cc(c1)OC(F)F)O)\N
InChI InChI=1S/C22H23ClF2N4O5/c1-33-28-19(26)13-4-2-12(3-5-13)11-27-20(31)17-6-7-29(17)21(32)18(30)14-8-15(23)10-16(9-14)34-22(24)25/h2-5,8-10,17-18,22,30H,6-7,11H2,1H3,(H2,26,28)(H,27,31)/t17-,18+/m0/s1
InChI Key XSNMGLZVFNDDPW-ZWKOTPCHSA-N
References
1. Cook D, Brown D, Alexander R, March R, Morgan P, Satterthwaite G, Pangalos MN. (2014)
Lessons learned from the fate of AstraZeneca's drug pipeline: a five-dimensional framework.
Nat Rev Drug Discov, 13 (6): 419-31. [PMID:24833294]
2. Lip GY, Rasmussen LH, Olsson SB, Zetterstrand S, Stahre C, Bylock A, Aunes-Jansson M, Eriksson U, Wåhlander K, Steering Committee. (2011)
Oral direct thrombin inhibitor AZD0837 for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation: a Phase II study of AZD0837 in patients who are appropriate for but unable or unwilling to take vitamin K antagonist therapy.
Thromb Res, 127 (2): 91-9. [PMID:21172721]