SRI-20864   Click here for help

GtoPdb Ligand ID: 10986

Synonyms: SRI20864
Compound class: Synthetic organic
Comment: SRI-20864 is an experimental antibacterial compound. It acts as an inhibitor of bacterial dihydrofolate reductase (DHFR; an antifolate antibacterial), and was generated in a programme that also included SRI-8858 [1]. These compounds were developed to treat trimethoprim-resistant Mycobacterium avium complex (MAC).
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 6
Topological polar surface area 121.2
Molecular weight 354.18
XLogP 1.91
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 CCOc1ccc(c(c1)NCc1cnc2c(c1C)c(N)nc(n2)N)OC
Isomeric SMILES CCOc1ccc(c(c1)NCc1cnc2c(c1C)c(N)nc(n2)N)OC
InChI InChI=1S/C18H22N6O2/c1-4-26-12-5-6-14(25-3)13(7-12)21-8-11-9-22-17-15(10(11)2)16(19)23-18(20)24-17/h5-7,9,21H,4,8H2,1-3H3,(H4,19,20,22,23,24)
InChI Key CRZVJULBIPRHRY-UHFFFAOYSA-N
References
1. Suling WJ, Seitz LE, Reynolds RC, Barrow WW. (2005)
New Mycobacterium avium antifolate shows synergistic effect when used in combination with dihydropteroate synthase inhibitors.
Antimicrob Agents Chemother, 49 (11): 4801-3. [PMID:16251337]