brodimoprim   Click here for help

GtoPdb Ligand ID: 12325

Synonyms: Ro 10-5970
Compound class: Synthetic organic
Comment: Brodimoprim belongs to the diaminopyrimidine class of compounds and is a structural analogue of trimethoprim. It inhibits bacterial dihydrofolate reductase (DHFR) and has antibacterial and antiprotozoal activities [3].

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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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 96.28
Molecular weight 338.04
XLogP 1.93
No. Lipinski's rules broken 0

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 COc1cc(Cc2cnc(nc2N)N)cc(c1Br)OC
Isomeric SMILES COc1cc(cc(c1Br)OC)Cc1cnc(nc1N)N
InChI InChI=1S/C13H15BrN4O2/c1-19-9-4-7(5-10(20-2)11(9)14)3-8-6-17-13(16)18-12(8)15/h4-6H,3H2,1-2H3,(H4,15,16,17,18)
InChI Key BFCRRLMMHNLSCP-UHFFFAOYSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[(4-bromo-3,5-dimethoxyphenyl)methyl]pyrimidine-2,4-diamine
International Nonproprietary Names Click here for help
INN number INN
4910 brodimoprim
Synonyms Click here for help
Ro 10-5970
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Brodimoprim
Other databases
CAS Registry No. 56518-41-3 (source: Scifinder)
ChEBI CHEBI:131726
ChEMBL Ligand CHEMBL31891
DrugBank Ligand DB13795
DrugCentral Ligand 398
GtoPdb PubChem SID 479821116
PubChem CID 68760
Search Google for chemical match using the InChIKey BFCRRLMMHNLSCP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BFCRRLMMHNLSCP
Search PubMed clinical trials brodimoprim
Search PubMed titles brodimoprim
Search PubMed titles/abstracts brodimoprim
UniChem Compound Search for chemical match using the InChIKey BFCRRLMMHNLSCP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BFCRRLMMHNLSCP-UHFFFAOYSA-N

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MedChemExpress
Brodimoprim (links to external site)
Cat. No. HY-121341