GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

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: Natural product
Comment: Streptomycin is an aminoglycoside antibacterial drug. Notably streptomycin was the first antibacterial cure for tuberculosis. As with other aminoglycosides, the most concerning side effects are renal and ear toxicities [2]. Streptomycin for clinical use is produced through biological fermentation of Streptomyces griseus bacteria which produce the compound naturally.

streptomycin is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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

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
Click here for help

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/)

✖
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

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/)
References
1. Hwang CH, Jaki BU, Klein LL, Lankin DC, McAlpine JB, Napolitano JG, Fryling NA, Franzblau SG, Cho SH, Stamets PE et al.. (2013)
Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis.
J Nat Prod, 76 (10): 1916-22. [PMID:24087924]
2. Prayle A, Watson A, Fortnum H, Smyth A. (2010)
Side effects of aminoglycosides on the kidney, ear and balance in cystic fibrosis.
Thorax, 65 (7): 654-8. [PMID:20627927]