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pezulepistat   Click here for help

GtoPdb Ligand ID: 14103

Synonyms: GDC-5780 | RG6319
Compound class: Synthetic organic
Comment: Pezulepistat (formerly RG6319 and GDC-5780) is the INN for an inhibitor of bacterial LepB with activity against Gram-negative bacteria (included in WHO INN proposed list 133, 10th July 2025). The chemical structure is claimed in patent WO2020243155A1 (Genentech and Hoffmann-La Roche) [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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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 24
Hydrogen bond donors 12
Rotatable bonds 20
Topological polar surface area 407.41
Molecular weight 1008.11
XLogP -5.81
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 CC1=NC(=NC(=C1C(=O)N[C@@H](CNS(=O)(=O)N)C(=O)N(C)[C@H]2C3=CC(=C(C(=C3)OC[C@@H](CN)O)O)C4=CC(=CC=C4OC[C@@H](CN)O)C[C@@H](C(=O)O)NC(=O)[C@H](C)NC2=O)N)C5=CC=C(C=C5)C(C)(C)C
Isomeric SMILES OC1=C2C3=C(OC[C@@H](CN)O)C=CC(=C3)C[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N(C([C@@H](NC(=O)C=4C(C)=NC(=NC4N)C5=CC=C(C(C)(C)C)C=C5)CNS(N)(=O)=O)=O)C)C(=C2)C=C1OC[C@@H](CN)O
InChI InChI=1S/C46H61N11O13S/c1-22-36(39(49)56-40(52-22)25-8-10-27(11-9-25)46(3,4)5)42(62)55-33(19-51-71(50,67)68)44(64)57(6)37-26-15-31(38(60)35(16-26)70-21-29(59)18-48)30-13-24(7-12-34(30)69-20-28(58)17-47)14-32(45(65)66)54-41(61)23(2)53-43(37)63/h7-13,15-16,23,28-29,32-33,37,51,58-60H,14,17-21,47-48H2,1-6H3,(H,53,63)(H,54,61)(H,55,62)(H,65,66)(H2,49,52,56)(H2,50,67,68)/t23-,28+,29+,32-,33-,37-/m0/s1
InChI Key MWMUFQHFVZYJCC-CPJAVKDOSA-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/)
References
1. Butler MS, Henderson IR, Capon RJ, Blaskovich MAT. (2023)
Antibiotics in the clinical pipeline as of December 2022.
J Antibiot (Tokyo), 76 (8): 431-473. [PMID:37291465]
2. Koehler MFT, Smith PA, Winter D, Sow B, Sturino C, Pelletier G, Boudreault J. (2020)
Macrocyclic broad spectrum antibiotics.
Patent number: WO2020243155A1. Assignee: Genentech and Hoffmann-La Roche. Priority date: 27/05/2020. Publication date: 03/12/2020.
3. Szałaj N, Benediktsdottir A, Rusin D, Karlén A, Mowbray SL, Więckowska A. (2022)
Bacterial type I signal peptidase inhibitors - Optimized hits from nature.
Eur J Med Chem, 238: 114490. [PMID:35660251]