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RO7075573   Click here for help

GtoPdb Ligand ID: 13375

PDB Ligand
Compound class: Synthetic organic
Comment: RO7075573 is a macrocyclic peptide with potent antibacterial against carbapenem-resistant Acinetobacter baumannii (CRAB) [2-4]. It is compound 38 claimed in Hoffmann-La Roche's patent WO2017072062A1 [1].
Optimization of this molecular class of compounds led to the development of the clinical candidate zosurabalpin.
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 11
Hydrogen bond donors 6
Rotatable bonds 9
Topological polar surface area 192.27
Molecular weight 739.76
XLogP 1.78
No. Lipinski's rules broken 3

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 CN1[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)NCC4=C(C(=CC=C4Cl)Cl)SC5=NC=CC=C5CN[C@@H](CCCN)C(=O)N[C@@H](CCCCN)C1=O
Isomeric SMILES CN1[C@H](C(=O)NCC2=C(C=CC(=C2SC3=C(CN[C@H](C(=O)N[C@H](C1=O)CCCCN)CCCN)C=CC=N3)Cl)Cl)CC4=CNC5=CC=CC=C54
InChI InChI=1S/C36H44Cl2N8O3S/c1-46-31(18-23-20-42-28-10-3-2-9-24(23)28)34(48)44-21-25-26(37)13-14-27(38)32(25)50-35-22(8-7-17-41-35)19-43-29(12-6-16-40)33(47)45-30(36(46)49)11-4-5-15-39/h2-3,7-10,13-14,17,20,29-31,42-43H,4-6,11-12,15-16,18-19,21,39-40H2,1H3,(H,44,48)(H,45,47)/t29-,30-,31-/m0/s1
InChI Key GBONSZKSVKTWGU-CHQNGUEUSA-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
(11S,14S,17S)-14-(4-aminobutyl)-11-(3-aminopropyl)-22,25-dichloro-17-(1H-indol-3-ylmethyl)-16-methyl-2-thia-4,10,13,16,19-pentazatricyclo[19.4.0.03,8]pentacosa-1(25),3(8),4,6,21,23-hexaene-12,15,18-trione
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo RO7075573
Other databases
BindingDB Ligand 651532
CAS Registry No. 2097284-11-0 (source: Scifinder)
GtoPdb PubChem SID 496703345
PubChem CID 129098768
RCSB PDB Ligand MG3
Search Google for chemical match using the InChIKey GBONSZKSVKTWGU-CHQNGUEUSA-N
Search Google for chemicals with the same backbone GBONSZKSVKTWGU
UniChem Compound Search for chemical match using the InChIKey GBONSZKSVKTWGU-CHQNGUEUSA-N
UniChem Connectivity Search for chemical match using the InChIKey GBONSZKSVKTWGU-CHQNGUEUSA-N