oritavancin   Click here for help

GtoPdb Ligand ID: 10877

Synonyms: Kimyrsa® | 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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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 CDK toolkit. 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 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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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.

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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
Kimyrsa® | LY-333328 | LY333328 | Orbactiv®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Oritavancin (Orbactiv), LY333328
Other databases
CAS Registry No. 171099-57-3 (source: PubChem)
ChEMBL Ligand CHEMBL1688530
DrugBank Ligand DB04911
DrugCentral Ligand 4678
GtoPdb PubChem SID 405560318
PubChem CID 16136912
Search Google for chemical match using the InChIKey VHFGEBVPHAGQPI-LXKZPTCJSA-N
Search Google for chemicals with the same backbone VHFGEBVPHAGQPI
Search PubMed clinical trials oritavancin
Search PubMed titles oritavancin
Search PubMed titles/abstracts oritavancin
UniChem Compound Search for chemical match using the InChIKey VHFGEBVPHAGQPI-LXKZPTCJSA-N
UniChem Connectivity Search for chemical match using the InChIKey VHFGEBVPHAGQPI-LXKZPTCJSA-N