vancomycin   Click here for help

GtoPdb Ligand ID: 10932

Synonyms: Vancocin® | Vancor®
Approved drug
vancomycin is an approved drug (FDA (1964), UK (1990))
Compound class: Natural product
Comment: Vancomycin is a complex glycopeptide antibacterial 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.
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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (1964), UK (1990))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
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 Vancomycin
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
Search Google for chemical match using the InChIKey MYPYJXKWCTUITO-LYRMYLQWSA-N
Search Google for chemicals with the same backbone MYPYJXKWCTUITO
Search PubMed clinical trials vancomycin
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UniChem Compound Search for chemical match using the InChIKey MYPYJXKWCTUITO-LYRMYLQWSA-N
UniChem Connectivity Search for chemical match using the InChIKey MYPYJXKWCTUITO-LYRMYLQWSA-N