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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2014), EMA (2015))
International Nonproprietary Names Click here for help
INN number INN
7978 dalbavancin
Synonyms Click here for help
BI-397 | BI397 | Dalvance® | Xydalba®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 135
Other databases
CAS Registry No. 171500-79-1 (source: PubChem)
GtoPdb PubChem SID 405560317
PubChem CID 23724878
Search Google for chemical match using the InChIKey KGPGQDLTDHGEGT-VBZOGQDBSA-N
Search Google for chemicals with the same backbone KGPGQDLTDHGEGT
Search PubMed clinical trials dalbavancin
Search PubMed titles dalbavancin
Search PubMed titles/abstracts dalbavancin
Search UniChem for chemical match using the InChIKey KGPGQDLTDHGEGT-VBZOGQDBSA-N
Search UniChem for chemicals with the same backbone KGPGQDLTDHGEGT