vancomycin   Click here for help

GtoPdb Ligand ID: 10932

Synonyms: Vancocin® | Vancor®
Approved drug
vancomycin is an approved drug (FDA (1964), UK (1990))
Comment: Vancomycin is a complex glycopeptide antibiotic that was originally isolated from Streptomyces orientalis. It has bactericidal activity against most organisms and is bacteriostatic vs. enterococci. Semisynthetic derivatives such as telavancin, dalbavancin and oritavancin are now available for clinical use.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 27
Hydrogen bond donors 19
Rotatable bonds 14
Topological polar surface area 530.49
Molecular weight 1447.43
XLogP 0.52
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@H]1O[C@@H](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(O)cc(cc3[C@H](NC2=O)C(=O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@](C1)(C)N)O
Isomeric SMILES OC[C@H]1O[C@@H](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(O)cc(cc3[C@H](NC2=O)C(=O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@](C1)(C)N)O
InChI InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
InChI Key MYPYJXKWCTUITO-LYRMYLQWSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1964), UK (1990))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
International Nonproprietary Names Click here for help
INN number INN
680 vancomycin
Synonyms Click here for help
Vancocin® | Vancor®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1505
Other databases
BindingDB Ligand 50335519
CAS Registry No. 1404-90-6 (source: PubChem)
ChEMBL Ligand CHEMBL262777
DrugBank Ligand DB00512
DrugCentral Ligand 2807
GtoPdb PubChem SID 405560373
PubChem CID 14969
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