Compound class:
Natural product
Comment: Liposidomycin B inhibits phospho-N-acetylmuramoyl-pentapeptide-transferase (MraY, translocase I), an essential enzyme in bacterial peptidoglycan biosynthesis [ 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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26
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Hydrogen bond donors
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8
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Rotatable bonds
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28
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Topological polar surface area
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386.54
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Molecular weight
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1010.07
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XLogP
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-2.32
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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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CC(C)CCCCCCCCC(CC(=O)OC1CN(C)C(C([C@@H]2[C@H]([C@H]([C@H](N3C=CC(=O)NC3=O)O2)O)O)O[C@H]4[C@@H]([C@@H]([C@@H](CN)O4)O)OS(=O)(=O)O)C(=O)N(C)C1C(=O)O)OC(=O)CC(C)CC(=O)O
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Isomeric SMILES
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CC(C)CCCCCCCCC(CC(=O)OC1CN(C(C(=O)N(C1C(=O)O)C)C([C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)O[C@H]4[C@@H]([C@@H]([C@H](O4)CN)O)OS(=O)(=O)O)C)OC(=O)CC(C)CC(=O)O
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InChI
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InChI=1S/C42H67N5O21S/c1-21(2)12-10-8-6-7-9-11-13-23(63-28(51)17-22(3)16-27(49)50)18-29(52)64-25-20-45(4)31(38(56)46(5)30(25)40(57)58)35(67-41-37(68-69(60,61)62)32(53)24(19-43)65-41)36-33(54)34(55)39(66-36)47-15-14-26(48)44-42(47)59/h14-15,21-25,30-37,39,41,53-55H,6-13,16-20,43H2,1-5H3,(H,49,50)(H,57,58)(H,44,48,59)(H,60,61,62)/t22?,23?,24-,25?,30?,31?,32-,33+,34-,35?,36+,37-,39-,41+/m1/s1
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InChI Key
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LGBOBVYRTQDYBA-ZUGGQKJLSA-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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