TBA-7371   Click here for help

GtoPdb Ligand ID: 13133

Synonyms: AZ-7371 | compound 1 [PMID:24957839] | TBA7371
Compound class: Synthetic organic
Comment: TBA-7371 was identified in a lead optimization study of a series of 1,4-azaindoles, a novel class of antibacterial compounds [1-3]. It has potent antimycobacterial activity and is under clinical evaluation as a treatment for tuberculosis (TB). TBA-7371 is a non-covalent inhibitor of decaprenylphosphoryl-beta-D-ribose oxidase (DprE1), an essential mycobacterial cell wall biosynthesis enzyme [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 8
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 98.88
Molecular weight 355.39
XLogP -0.61
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 CC1=CN=C2C(=CN(CC3=NC=NC(=C3C)OC)C2=C1)C(=O)NCCO
Isomeric SMILES CC1=CC2=C(C(=CN2CC3=C(C(=NC=N3)OC)C)C(=O)NCCO)N=C1
InChI InChI=1S/C18H21N5O3/c1-11-6-15-16(20-7-11)13(17(25)19-4-5-24)8-23(15)9-14-12(2)18(26-3)22-10-21-14/h6-8,10,24H,4-5,9H2,1-3H3,(H,19,25)
InChI Key VDRYGTNDKXIPSK-UHFFFAOYSA-N
References
1. Chatterji M, Shandil R, Manjunatha MR, Solapure S, Ramachandran V, Kumar N, Saralaya R, Panduga V, Reddy J, Prabhakar KR et al.. (2014)
1,4-azaindole, a potential drug candidate for treatment of tuberculosis.
Antimicrob Agents Chemother, 58 (9): 5325-31. [PMID:24957839]
2. Shirude PS, Shandil R, Sadler C, Naik M, Hosagrahara V, Hameed S, Shinde V, Bathula C, Humnabadkar V, Kumar N et al.. (2013)
Azaindoles: noncovalent DprE1 inhibitors from scaffold morphing efforts, kill Mycobacterium tuberculosis and are efficacious in vivo.
J Med Chem, 56 (23): 9701-8. [PMID:24215368]
3. Shirude PS, Shandil RK, Manjunatha MR, Sadler C, Panda M, Panduga V, Reddy J, Saralaya R, Nanduri R, Ambady A et al.. (2014)
Lead optimization of 1,4-azaindoles as antimycobacterial agents.
J Med Chem, 57 (13): 5728-37. [PMID:24874895]