macozinone   Click here for help

GtoPdb Ligand ID: 13055

Synonyms: PBTZ169
Compound class: Synthetic organic
Comment: Macozinone (PBTZ169) is the lead from a series of piperazine-containing benzothiazinones [1]. It has potent antimycobacterial activity and is under clinical evaluation as a treatment for tuberculosis (TB). Macozinone is an 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 4
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 104.35
Molecular weight 456.48
XLogP 4.49
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 C1CCC(CC1)CN2CCN(CC2)C3=NC(=O)C4=CC(=CC(=C4S3)[N+](=O)[O-])C(F)(F)F
Isomeric SMILES C1CCC(CC1)CN2CCN(CC2)C3=NC(=O)C4=C(S3)C(=CC(=C4)C(F)(F)F)[N+](=O)[O-]
InChI InChI=1S/C20H23F3N4O3S/c21-20(22,23)14-10-15-17(16(11-14)27(29)30)31-19(24-18(15)28)26-8-6-25(7-9-26)12-13-4-2-1-3-5-13/h10-11,13H,1-9,12H2
InChI Key BJDZBXGJNBMCAV-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-1,3-benzothiazin-4-one
International Nonproprietary Names Click here for help
INN number INN
10732 macozinone
Synonyms Click here for help
PBTZ169
Database Links Click here for help
BindingDB Ligand 50515570
CAS Registry No. 1377239-83-2 (source: Scifinder)
ChEMBL Ligand CHEMBL3330226
DrugBank Ligand DB14821
GtoPdb PubChem SID 491299837
PubChem CID 57331386
Search Google for chemical match using the InChIKey BJDZBXGJNBMCAV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BJDZBXGJNBMCAV
Search PubMed clinical trials macozinone
Search PubMed titles macozinone
Search PubMed titles/abstracts macozinone
UniChem Compound Search for chemical match using the InChIKey BJDZBXGJNBMCAV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BJDZBXGJNBMCAV-UHFFFAOYSA-N