oritavancin   Click here for help

GtoPdb Ligand ID: 10877

Synonyms: LY-333328 | LY333328 | Orbactiv®
Approved drug
oritavancin is an approved drug (FDA (2014), EMA (2015))
Compound class: Synthetic organic
Comment: Oritavancin is a semi-synthetic glycopeptide antibacterial drug [1]. It is structurally related to vancomycin, and likewise is active against several Gram-positive organisms including methicillin resistant Staphylococcus aureus (MRSA). Like dalbavancin, it offers the option of single-dose administration.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 30
Hydrogen bond donors 20
Rotatable bonds 20
Topological polar surface area 560.98
Molecular weight 1790.56
XLogP 5.3
No. Lipinski's rules broken 4
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@H]1O[C@@H](Oc2c3Oc4ccc(cc4Cl)[C@@H](O)[C@@H](NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](C(=O)N[C@@H]4c(c3)cc2Oc2ccc(cc2Cl)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@@](C2)(C)N)O)[C@@H]2NC(=O)[C@H](NC4=O)c3ccc(c(c3)c3c(O)cc(cc3[C@H](NC2=O)C(=O)O)O)O)CC(=O)N)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@](C1)(C)NCc1ccc(cc1)c1ccc(cc1)Cl)O
Isomeric SMILES OC[C@H]1O[C@@H](Oc2c3Oc4ccc(cc4Cl)[C@@H](O)[C@@H](NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](C(=O)N[C@@H]4c(c3)cc2Oc2ccc(cc2Cl)[C@@H](O[C@@H]2O[C@@H](C)[C@@H]([C@@](C2)(C)N)O)[C@@H]2NC(=O)[C@H](NC4=O)c3ccc(c(c3)c3c(O)cc(cc3[C@H](NC2=O)C(=O)O)O)O)CC(=O)N)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@](C1)(C)NCc1ccc(cc1)c1ccc(cc1)Cl)O
InChI InChI=1S/C86H97Cl3N10O26/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-/m0/s1
InChI Key VHFGEBVPHAGQPI-LXKZPTCJSA-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
7979 oritavancin
Synonyms Click here for help
LY-333328 | LY333328 | Orbactiv®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 132
Other databases
CAS Registry No. 171099-57-3 (source: PubChem)
ChEMBL Ligand CHEMBL1688530
DrugBank Ligand DB04911
GtoPdb PubChem SID 405560318
PubChem CID 16136912
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