compound 16 [PMID: 38385364]   Click here for help

GtoPdb Ligand ID: 13259

Compound class: Synthetic organic
Comment: Compound 16 is the lead from a series of triaromatic pleuromulin compounds with Gram-positive antibacterial activity [1]. It is also one of the compounds claimed in patent WO2021219813 [2].
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 14
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 159.51
Molecular weight 722.88
XLogP 2.12
No. Lipinski's rules broken 2
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 C=C[C@]1(C)C[C@H]([C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@@H]23)[C@@H](C)[C@@H]1O)OC(=O)CN4C=C(C5=CN=C(C=C5)CN6C=NC7=C6N=CN=C7N8CCNCC8)N=N4
Isomeric SMILES C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CN4C=C(N=N4)C5=CN=C(C=C5)CN6C=NC7=C6N=CN=C7N8CCNCC8)C
InChI InChI=1S/C39H50N10O4/c1-6-37(4)17-30(38(5)24(2)9-11-39(25(3)34(37)52)12-10-29(50)33(38)39)53-31(51)21-49-20-28(45-46-49)26-7-8-27(41-18-26)19-48-23-44-32-35(42-22-43-36(32)48)47-15-13-40-14-16-47/h6-8,18,20,22-25,30,33-34,40,52H,1,9-17,19,21H2,2-5H3/t24-,25+,30-,33+,34+,37-,38+,39+/m1/s1
InChI Key JMWFCYTVJBGCRD-ODXCVMAQSA-N
References
1. Heidtmann CV, Fejer AR, Stærk K, Pedersen M, Asmussen MG, Hertz FB, Prabhala BK, Frimodt-Møller N, Klitgaard JK, Andersen TE et al.. (2024)
Hit-to-Lead Identification and Validation of a Triaromatic Pleuromutilin Antibiotic Candidate.
J Med Chem, 67 (5): 3692-3710. [PMID:38385364]
2. Nielsen P, Heidtmann CV. (2021)
Antibacterial and antifungal pleuromutilin conjugates.
Patent number: WO2021219813A1. Assignee: Syddansk Universitet. Priority date: 29/04/2021. Publication date: 04/11/2021.