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].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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33
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Hydrogen bond donors
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16
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Rotatable bonds
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34
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Topological polar surface area
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530.41
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Molecular weight
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1383.77
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XLogP
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7.64
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No. Lipinski's rules broken
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4
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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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SMILES / InChI / InChIKey
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Canonical SMILES
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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
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Isomeric SMILES
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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
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InChI
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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
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InChI Key
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RRAOZJHXDSMGMH-LOKPQUDHSA-N
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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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