capreomycin IB   Click here for help

GtoPdb Ligand ID: 13256

Synonyms: Capastat®
Approved drug
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.
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 21
Hydrogen bond donors 13
Rotatable bonds 11
Topological polar surface area 358.19
Molecular weight 652.71
XLogP -3.74
No. Lipinski's rules broken 3

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 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
Isomeric SMILES 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
InChI 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
InChI Key FRXNXDHFQYZYNA-OJBVOROPSA-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. Bycroft BW, Cameron D, Croft LR, Hassanali-Walji A, Johnson AW, Webb T. (1971)
Total structure of capreomycin IB, a tuberculostatic peptide antibiotic.
Nature, 231 (5301): 301-2. [PMID:4325287]
2. Herr Jr EB, Redstone MO. (1966)
Chemical and physical characterization of capreomycin.
Ann N Y Acad Sci, 135 (2): 940-6. [PMID:5220248]