Synonyms: TD-6424 | TD6424 | Vibativ®
telavancin is an approved drug (FDA (2009), EMA (2011))
Comment: Telavancin is a glycopeptide antibacterial drug that is derived from vancomycin [ 1]. It is used to treat Gram-positive infections, including MRSA.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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32
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Hydrogen bond donors
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23
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Rotatable bonds
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31
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Topological polar surface area
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607.9
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Molecular weight
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1753.64
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XLogP
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5.94
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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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CCCCCCCCCCNCCN[C@@]1(C)C[C@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO)Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c([C@H](NC2=O)C(=O)O)cc(c(c3O)CNCP(=O)(O)O)O)O)O[C@H]([C@H]1O)C
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Isomeric SMILES
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CCCCCCCCCCNCCN[C@@]1(C)C[C@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)CO)Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c([C@H](NC2=O)C(=O)O)cc(c(c3O)CNCP(=O)(O)O)O)O)O[C@H]([C@H]1O)C
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InChI
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InChI=1S/C80H106Cl2N11O27P/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114)/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-/m0/s1
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InChI Key
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ONUMZHGUFYIKPM-MXNFEBESSA-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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