plusbacin A3   Click here for help

GtoPdb Ligand ID: 11020

Compound class: Natural product
Comment: Plusbacin A3 was isolated from Pseudomonas sp. PB-6250 [3]. It acts as a peptidoglycan synthesis inhibitor in methicillin-resistant Staphylococcus aureus [2]. Plusbacin A3 can be chemically synthesised [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 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 33
Hydrogen bond donors 16
Rotatable bonds 34
Topological polar surface area 530.41
Molecular weight 1383.77
XLogP 7.64
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 CCCCCCCCCCCC1OC(=O)[C@@H](NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@@H](CO)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@H](NC(=O)[C@H](N(C(=O)C1)C(=O)CC(CCCCCCCCCCC(C)C)O)[C@H](O)C)C)CC[C@@H]2O)CCCN=C(N)N)[C@H](C(=O)O)O)[C@@H](C(=O)O)O
Isomeric SMILES CCCCCCCCCCCC1OC(=O)[C@@H](NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@@H](CO)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@H](NC(=O)[C@H](N(C(=O)C1)C(=O)CC(CCCCCCCCCCC(C)C)O)[C@H](O)C)C)CC[C@@H]2O)CCCN=C(N)N)[C@H](C(=O)O)O)[C@@H](C(=O)O)O
InChI InChI=1S/C64H109N11O22/c1-6-7-8-9-10-11-16-19-22-26-40-34-46(82)75(45(81)33-39(78)25-21-18-15-13-12-14-17-20-24-36(2)3)49(38(5)77)56(87)68-37(4)59(90)73-31-28-43(79)50(73)57(88)69-41(27-23-30-67-64(65)66)54(85)71-47(52(83)61(92)93)55(86)70-42(35-76)60(91)74-32-29-44(80)51(74)58(89)72-48(63(96)97-40)53(84)62(94)95/h36-44,47-53,76-80,83-84H,6-35H2,1-5H3,(H,68,87)(H,69,88)(H,70,86)(H,71,85)(H,72,89)(H,92,93)(H,94,95)(H4,65,66,67)/t37-,38-,39?,40?,41+,42-,43+,44+,47-,48+,49-,50+,51+,52-,53+/m1/s1
InChI Key RRAOZJHXDSMGMH-LOKPQUDHSA-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. Katsuyama A, Paudel A, Panthee S, Hamamoto H, Kawakami T, Hojo H, Yakushiji F, Ichikawa S. (2017)
Total Synthesis and Antibacterial Investigation of Plusbacin A3.
Org Lett, 19 (14): 3771-3774. [PMID:28696114]
2. Maki H, Miura K, Yamano Y. (2001)
Katanosin B and plusbacin A(3), inhibitors of peptidoglycan synthesis in methicillin-resistant Staphylococcus aureus.
Antimicrob Agents Chemother, 45 (6): 1823-7. [PMID:11353632]
3. Shoji J, Hinoo H, Katayama T, Nakagawa Y, Ikenishi Y, Iwatani K, Yoshida T. (1992)
Structures of new peptide antibiotics, plusbacins A1-A4 and B1-B4.
J Antibiot, 45 (6): 824-31. [PMID:1500346]