streptomycin   Click here for help

GtoPdb Ligand ID: 10923

Synonyms: Gerox⪚ | NSC-14083 | Strepcen®
Approved drug PDB Ligand
streptomycin is an approved drug (FDA (1946))
Compound class: Synthetic organic
Comment: Streptomycin is an aminoglycoside antibacterial drug. Notably streptomycin was the first antibiotic cure for tuberculosis. As with other aminoglycosides, the most concerning side effects are renal and ear toxicities [2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 19
Hydrogen bond donors 12
Rotatable bonds 9
Topological polar surface area 336.43
Molecular weight 581.27
XLogP -5.99
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES OC[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H]([C@H]([C@@H]3N=C(N)N)O)N=C(N)N)O[C@H]([C@]2(O)C=O)C)[C@H]([C@@H]([C@H]1O)O)NC
Isomeric SMILES OC[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H]([C@H]([C@@H]3N=C(N)N)O)N=C(N)N)O[C@H]([C@]2(O)C=O)C)[C@H]([C@@H]([C@H]1O)O)NC
InChI InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
InChI Key UCSJYZPVAKXKNQ-HZYVHMACSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1946))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
International Nonproprietary Names Click here for help
INN number INN
3685 streptomycin
Synonyms Click here for help
Gerox⪚ | NSC-14083 | Strepcen®
Database Links Click here for help
BindingDB Ligand 50103513
CAS Registry No. 57-92-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL372795
DrugBank Ligand DB01082
DrugCentral Ligand 2481
GtoPdb PubChem SID 405560364
PubChem CID 19649
RCSB PDB Ligand SRY
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