gentamicin   Click here for help

GtoPdb Ligand ID: 2427

Synonyms: Garamycin® | gentamicin sulfate
Approved drug
gentamicin is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: The approved drug gentamicin is a complex of three closely-related aminoglycoside sulfates: C1, C1a and C2. The structure shown here is representative of the general structure of the compounds. For more information on the structure of the individual components of gentamicin, please see the relevant entries on ChEBI: (CHEBI:27412, CHEBI:27784, CHEBI:28292).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 8
Rotatable bonds 7
Topological polar surface area 199.73
Molecular weight 477.32
XLogP -2.88
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CNC(C1CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N)C
Isomeric SMILES CNC(C1CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N)C
InChI InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3
InChI Key CEAZRRDELHUEMR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1970))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
2-[4,6-diamino-3-[3-amino-6-(1-methylaminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol
International Nonproprietary Names Click here for help
INN number INN
1617 gentamicin
Synonyms Click here for help
Garamycin® | gentamicin sulfate
Database Links Click here for help
ChEMBL Ligand CHEMBL329592
DrugBank Ligand DB00798
GtoPdb PubChem SID 135650301
PubChem CID 3467
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Wikipedia Gentamicin