Synonyms: Capastat®
capreomycin IB is an approved drug (UK, FDA (1971))
Compound class:
Natural product
Comment: Capreomycin is a tuberactinomycin antibacterial, originally isolated from cultures of Streptomyces capreolus as a mixture of four components (capreomycins IA, IB, IIA, and IIB) [ 2]. We show the structure for capreomycin IB, a cyclic depsipeptide, which is reported to be the major component of capreomycin [ 1]. Note that the INN describes a mixture of capreomycin IA and IB, represented by PubChem CID 3000502.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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21
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Hydrogen bond donors
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13
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Rotatable bonds
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11
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Topological polar surface area
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358.19
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Molecular weight
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652.71
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XLogP
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-3.74
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No. Lipinski's rules broken
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3
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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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C[C@H]1C(=O)N[C@@H](CNC(=O)C[C@H](CCCN)N)C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@@H]([C@H]2CCNC(=N2)N)C(=O)NC[C@@H](C(=O)N1)N
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Isomeric SMILES
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C[C@H]1C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H](C(=O)NC[C@@H](C(=O)N1)N)[C@H]2CCNC(=N2)N)CNC(=O)C[C@H](CCCN)N
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InChI
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InChI=1S/C25H44N14O7/c1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b16-10+/t11-,12-,13-,14+,15-,18-/m0/s1
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InChI Key
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FRXNXDHFQYZYNA-OJBVOROPSA-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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