dalbavancin   Click here for help

GtoPdb Ligand ID: 10876

Synonyms: BI-397 | BI397 | Dalvance® | Xydalba®
Approved drug
dalbavancin is an approved drug (FDA (2014), EMA (2015))
Compound class: Synthetic organic
Comment: Dalbavancin is a second-generation, semi-synthetic lipoglycopeptide antibiotic [1-2]. It has been modified to increase activity and allow once-weekly dosing. Dalbavancin inhibits cross-linking of bacterial cell wall peptidoglycans, and thereby disrupts bacterial cell wall synthesis. It has little activity against Gram-negative bacilli [3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 29
Hydrogen bond donors 21
Rotatable bonds 24
Topological polar surface area 572.51
Molecular weight 1814.61
XLogP 8.2
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@H]1O[C@H](Oc2cc(O)cc3c2c2cc(ccc2O)[C@H]2NC(=O)[C@@H]4NC(=O)[C@H]5NC(=O)[C@@H](Cc6ccc(Oc7cc4cc(Oc4ccc([C@H]([C@@H](C(=O)NC3C(=O)NCCCN(C)C)NC2=O)O)cc4Cl)c7O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2NC(=O)CCCCCCCCC(C)C)O)O)cc6)NC(=O)[C@H](NC)c2cc(Oc3cc5c(Cl)c(c3)O)c(O)cc2)[C@H]([C@H]([C@@H]1O)O)O
Isomeric SMILES OC[C@H]1O[C@H](Oc2cc(O)cc3c2c2cc(ccc2O)[C@H]2NC(=O)[C@@H]4NC(=O)[C@H]5NC(=O)[C@@H](Cc6ccc(Oc7cc4cc(Oc4ccc([C@H]([C@@H](C(=O)NC3C(=O)NCCCN(C)C)NC2=O)O)cc4Cl)c7O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2NC(=O)CCCCCCCCC(C)C)O)O)cc6)NC(=O)[C@H](NC)c2cc(Oc3cc5c(Cl)c(c3)O)c(O)cc2)[C@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C88H100Cl2N10O28/c1-38(2)13-10-8-6-7-9-11-14-61(106)94-70-73(109)75(111)78(86(120)121)128-87(70)127-77-58-31-43-32-59(77)124-55-24-19-42(29-50(55)89)71(107)69-85(119)98-67(80(114)92-25-12-26-100(4)5)48-33-44(102)34-57(125-88-76(112)74(110)72(108)60(37-101)126-88)62(48)47-28-40(17-22-52(47)103)65(82(116)99-69)95-83(117)66(43)96-84(118)68-49-35-46(36-54(105)63(49)90)123-56-30-41(18-23-53(56)104)64(91-3)81(115)93-51(79(113)97-68)27-39-15-20-45(122-58)21-16-39/h15-24,28-36,38,51,60,64-76,78,87-88,91,101-105,107-112H,6-14,25-27,37H2,1-5H3,(H,92,114)(H,93,115)(H,94,106)(H,95,117)(H,96,118)(H,97,113)(H,98,119)(H,99,116)(H,120,121)/t51-,60-,64-,65-,66-,67?,68+,69+,70-,71-,72-,73-,74+,75+,76+,78+,87-,88+/m1/s1
InChI Key KGPGQDLTDHGEGT-VBZOGQDBSA-N