brilacidin   Click here for help

GtoPdb Ligand ID: 13807

Synonyms: MMV1634402 | PMX30063
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Brilacidin is a small molecule mimetic of defensin, an antimicrobial peptide (also referred to as a host defence peptide) [6]. Brilacidin has anti-inflammatory properties and exhibits broad-spectrum antimicrobial activity, including antibacterial [4,6], antimalarial [1], antifungal [5], and antiviral [2-3]. Brilacidin (MMV1634402) was one of the chemotypes included in the Medicines for Malaria Pandemic Response Box.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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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Click here for structure editor
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 20
Hydrogen bond donors 10
Rotatable bonds 26
Topological polar surface area 312.44
Molecular weight 936.91
XLogP -0.5
No. Lipinski's rules broken 4

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 C(CCN=C(N)N)CC(=O)NC1=CC(=CC(=C1O[C@@H]2CCNC2)NC(=O)C3=NC=NC(=C3)C(=O)NC4=C(C(=CC(=C4)C(F)(F)F)NC(=O)CCCCN=C(N)N)O[C@@H]5CCNC5)C(F)(F)F
Isomeric SMILES C1CNC[C@@H]1OC2=C(C=C(C=C2NC(=O)C3=CC(=NC=N3)C(=O)NC4=CC(=CC(=C4O[C@@H]5CCNC5)NC(=O)CCCCN=C(N)N)C(F)(F)F)C(F)(F)F)NC(=O)CCCCN=C(N)N
InChI InChI=1S/C40H50F6N14O6/c41-39(42,43)21-13-25(57-31(61)5-1-3-9-53-37(47)48)33(65-23-7-11-51-18-23)27(15-21)59-35(63)29-17-30(56-20-55-29)36(64)60-28-16-22(40(44,45)46)14-26(34(28)66-24-8-12-52-19-24)58-32(62)6-2-4-10-54-38(49)50/h13-17,20,23-24,51-52H,1-12,18-19H2,(H,57,61)(H,58,62)(H,59,63)(H,60,64)(H4,47,48,53)(H4,49,50,54)/t23-,24-/m1/s1
InChI Key QPDYBCZNGUJZDK-DNQXCXABSA-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
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
4-N,6-N-bis[3-[5-(diaminomethylideneamino)pentanoylamino]-2-[(3R)-pyrrolidin-3-yl]oxy-5-(trifluoromethyl)phenyl]pyrimidine-4,6-dicarboxamide
International Nonproprietary Names Click here for help
INN number INN
9693 brilacidin
Synonyms Click here for help
MMV1634402 | PMX30063
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Brilacidin
Other databases
CAS Registry No. 1224095-98-0 (source: Scifinder)
ChEMBL Ligand CHEMBL2219413
DrugBank Ligand DB12997
GtoPdb PubChem SID 507750440
PubChem CID 25023695
Search Google for chemical match using the InChIKey QPDYBCZNGUJZDK-DNQXCXABSA-N
Search Google for chemicals with the same backbone QPDYBCZNGUJZDK
Search PubMed clinical trials brilacidin
Search PubMed titles brilacidin
Search PubMed titles/abstracts brilacidin
UniChem Compound Search for chemical match using the InChIKey QPDYBCZNGUJZDK-DNQXCXABSA-N
UniChem Connectivity Search for chemical match using the InChIKey QPDYBCZNGUJZDK-DNQXCXABSA-N
Wikipedia Brilacidin