dihydrostreptomycin   Click here for help

GtoPdb Ligand ID: 12163

Approved drug PDB Ligand
dihydrostreptomycin is an approved drug
Compound class: Synthetic organic
Comment: Dihydrostreptomycin is an aminoglycoside antibacterial drug and a derivative of streptomycin [1].
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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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 19
Hydrogen bond donors 13
Rotatable bonds 9
Topological polar surface area 339.59
Molecular weight 583.28
XLogP -6.25
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
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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](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)CO)C)[C@H]([C@@H]([C@H]1O)O)NC
Isomeric SMILES C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@H]([C@@H]([C@H]1O)O)N=C(N)N)O)N=C(N)N)O[C@H]1[C@H]([C@@H]([C@H]([C@@H](O1)CO)O)O)NC)(CO)O
InChI InChI=1S/C21H41N7O12/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/h5-18,26,29-36H,3-4H2,1-2H3,(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 ASXBYYWOLISCLQ-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
Withdrawn drug? Yes
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-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine
International Nonproprietary Names Click here for help
INN number INN
1574 dihydrostreptomycin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Dihydrostreptomycin
Other databases
CAS Registry No. 128-46-1 (source: Scifinder)
ChEBI CHEBI:38291
ChEMBL Ligand CHEMBL1950576
DrugBank Ligand DB11512
DrugCentral Ligand 890
GtoPdb PubChem SID 472319285
PubChem CID 439369
RCSB PDB Ligand 71R
Search Google for chemical match using the InChIKey ASXBYYWOLISCLQ-HZYVHMACSA-N
Search Google for chemicals with the same backbone ASXBYYWOLISCLQ
Search PubMed clinical trials dihydrostreptomycin
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Search PubMed titles/abstracts dihydrostreptomycin
UniChem Compound Search for chemical match using the InChIKey ASXBYYWOLISCLQ-HZYVHMACSA-N
UniChem Connectivity Search for chemical match using the InChIKey ASXBYYWOLISCLQ-HZYVHMACSA-N