wollamide B   Click here for help

GtoPdb Ligand ID: 13452

Compound class: Natural product
Comment: Wollamide B is a cyclic hexapeptide antibacterial compound with activity against Gram-positive bacteria and mycobacteria. The compound was initially isolated from Streptomyces MST-115088 [3].
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 16
Hydrogen bond donors 9
Rotatable bonds 12
Topological polar surface area 255.74
Molecular weight 739.91
XLogP 3.42
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 CC(C)C[C@H]1C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H](CCCN)C(=O)N[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)N1
Isomeric SMILES CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CNC3=CC=CC=C32)CCCN)CC(=O)N)C(C)C)CC(C)C
InChI InChI=1S/C37H57N9O7/c1-19(2)14-26-33(49)43-27(15-20(3)4)36(52)46-31(21(5)6)37(53)45-29(17-30(39)47)35(51)41-25(12-9-13-38)32(48)44-28(34(50)42-26)16-22-18-40-24-11-8-7-10-23(22)24/h7-8,10-11,18-21,25-29,31,40H,9,12-17,38H2,1-6H3,(H2,39,47)(H,41,51)(H,42,50)(H,43,49)(H,44,48)(H,45,53)(H,46,52)/t25-,26+,27-,28+,29+,31+/m1/s1
InChI Key OXJJMHSZSDGXNW-SCJLKASNSA-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. Asfaw H, Laqua K, Walkowska AM, Cunningham F, Martinez-Martinez MS, Cuevas-Zurita JC, Ballell-Pages L, Imming P. (2017)
Design, synthesis and structure-activity relationship study of wollamide B; a new potential anti TB agent.
PLoS One, 12 (4): e0176088. [PMID:28423019]
2. Khalil ZG, Hill TA, De Leon Rodriguez LM, Lohman RJ, Hoang HN, Reiling N, Hillemann D, Brimble MA, Fairlie DP, Blumenthal A et al.. (2019)
Structure-Activity Relationships of Wollamide Cyclic Hexapeptides with Activity against Drug-Resistant and Intracellular Mycobacterium tuberculosis.
Antimicrob Agents Chemother, 63 (3). [PMID:30602509]
3. Khalil ZG, Salim AA, Lacey E, Blumenthal A, Capon RJ. (2014)
Wollamides: antimycobacterial cyclic hexapeptides from an Australian soil Streptomyces.
Org Lett, 16 (19): 5120-3. [PMID:25229313]
4. Rollo RF, Mori G, Hill TA, Hillemann D, Niemann S, Homolka S, Fairlie DP, Blumenthal A. (2023)
Wollamide Cyclic Hexapeptides Synergize with Established and New Tuberculosis Antibiotics in Targeting Mycobacterium tuberculosis.
Microbiol Spectr, 11 (4): e0046523. [PMID:37289062]