epiroprim   Click here for help

GtoPdb Ligand ID: 12327

Synonyms: Ro 11-8958 | TCMDC-137295
Compound class: Synthetic organic
Comment: Epiroprim belongs to the diaminopyrimidine class of antimicrobial compounds and is a structural analogue of trimethoprim [3]. It inhibits bacterial dihydrofolate reductase (DHFR) and has antibacterial and antiparasitic activities [2-3].
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 4
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 100.69
Molecular weight 353.19
XLogP 2.65
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 CCOc1cc(cc(c1n1cccc1)OCC)Cc1cnc(nc1N)N
Isomeric SMILES CCOc1cc(cc(c1n1cccc1)OCC)Cc1cnc(nc1N)N
InChI InChI=1S/C19H23N5O2/c1-3-25-15-10-13(9-14-12-22-19(21)23-18(14)20)11-16(26-4-2)17(15)24-7-5-6-8-24/h5-8,10-12H,3-4,9H2,1-2H3,(H4,20,21,22,23)
InChI Key NMARPFMJVCXSAV-UHFFFAOYSA-N
References
1. Locher HH, Schlunegger H, Hartman PG, Angehrn P, Then RL. (1996)
Antibacterial activities of epiroprim, a new dihydrofolate reductase inhibitor, alone and in combination with dapsone.
Antimicrob Agents Chemother, 40 (6): 1376-81. [PMID:8726004]
2. Mehlhorn H, Dankert W, Hartman PG, Then RL. (1995)
A pilot study on the efficacy of epiroprim against developmental stages of Toxoplasma gondii and Pneumocystis carinii in animal models.
Parasitol Res, 81 (4): 296-301. [PMID:7624286]
3. Then RL, Böhni E, Angehrn P, Plozza-Nottebrock H, Stoeckel K. (1982)
New analogs of trimethoprim.
Rev Infect Dis, 4 (2): 372-7. [PMID:7051237]