STREPTOMYCIN

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Synonyms
Status
Molecule Category Free-form
ATC A07AA04 J01GA01
UNII Y45QSO73OB
EPA CompTox DTXSID4023597

Structure

InChI Key UCSJYZPVAKXKNQ-HZYVHMACSA-N
Smiles CN[C@@H]1[C@H](O[C@H]2[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]3N=C(N)N)O[C@@H](C)[C@]2(O)C=O)O[C@@H](CO)[C@H](O)[C@H]1O
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H39N7O12
Molecular Weight 581.58
AlogP -8.16
Hydrogen Bond Acceptor 15.0
Hydrogen Bond Donor 12.0
Number of Rotational Bond 9.0
Polar Surface Area 336.43
Molecular species BASE
Aromatic Rings 0.0
Heavy Atoms 40.0
Assay Description Organism Bioactivity Reference
Antibacterial activity against gram positive bacteria Enterococcus faecalis was determined by twofold Micro-broth dilution assay Enterococcus faecalis 1.25 ug.mL-1
Antibacterial activity against gram negative bacteria Enterobacter aerogens was determined by twofold Micro-broth dilution assay Enterobacter aerogenes 1.25 ug.mL-1
Antibacterial activity against gram negative bacteria Escherichia coli was determined by twofold Micro-broth dilution assay Escherichia coli 1.25 ug.mL-1
Maximal inhibition against the displacement of Picogreen from fMet-tRNA(fMet) by the aminoglycoside Staphylococcus aureus 95.0 %
Maximal inhibition of the aminoglycoside on Staphylococcus aureus IF-2 binding to fMet-tRNA(fMet) Staphylococcus aureus 43.0 %
Antibacterial activity against gram negative bacteria Salmonella typhi was determined by twofold Micro-broth dilution assay Salmonella enterica subsp. enterica serovar Typhi 1.25 ug.mL-1
Antibacterial activity against gram negative bacteria Salmonella Typhimurium was determined by twofold Micro-broth dilution assay Salmonella enterica subsp. enterica serovar Typhimurium 1.25 ug.mL-1
Antibacterial activity against gram negative bacteria Shigella flexenerii was determined by twofold Micro-broth dilution assay Shigella flexneri 1.25 ug.mL-1
Antibacterial activity against gram positive bacteria Staphylococcus aureus was determined by twofold Micro-broth dilution assay Staphylococcus aureus 0.3 ug.mL-1
Antibacterial activity against gram positive bacteria Staphylococcus epidermidis was determined by twofold Micro-broth dilution assay Staphylococcus epidermidis 0.12 ug.mL-1
Antibacterial activity against gram positive bacteria Streptococcus mutans was determined by twofold Micro-broth dilution assay Streptococcus mutans 0.12 ug.mL-1
Cytotoxicity against Vero cells after 48 hrs by XTT method Chlorocebus sabaeus 120.0 ug.mL-1
Antitubercular activity against Mycobacterium tuberculosis H37Rv at 7.25 ug/ml by microplate alamar blue assay Mycobacterium tuberculosis H37Rv 100.0 %
Antibacterial activity against Escherichia coli ATCC 35218 Escherichia coli 0.73 ug.mL-1
Antimycobacterial activity against Mycobacterium smegmatis assessed as growth inhibition in mid-logarithmic phase by spectrophotometry Mycobacterium smegmatis 500.0 nM
Antimycobacterial activity against Mycobacterium smegmatis by GFP-based fluorescence assay Mycobacterium smegmatis 480.0 nM
Antimicrobial activity against Escherichia coli at 2000 ug after 24 hr by disk diffusion method relative to control Escherichia coli 64.0 %
Antimicrobial activity against Pseudomonas aeruginosa at 2000 ug after 24 hr by disk diffusion method relative to control Pseudomonas aeruginosa 64.0 %
Antimicrobial activity against Klebsiella pneumoniae at 2000 ug after 24 hr by disk diffusion method relative to control Klebsiella pneumoniae 64.0 %
Antimicrobial activity against Bacillus subtilis at 2000 ug after 24 hr by disk diffusion method relative to control Bacillus subtilis 64.0 %
Antimicrobial activity against Staphylococcus aureus at 2000 ug after 24 hr by disk diffusion method relative to control Staphylococcus aureus 45.0 %
Cytotoxicity against african green monkey Vero cells after 72 hrs by MTS-PMS assay Chlorocebus sabaeus 100.0 ug.mL-1
Cytotoxicity against African green monkey Vero cells assessed as cell viability after 72 hrs by MTT assay Chlorocebus sabaeus 50.0 ug.mL-1
Binding affinity to biotinylated pre-miRNA-21 (unknown origin) by SPR analysis Not specified 100.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 17076
ChEMBL CHEMBL372795
DrugBank DB01082
DrugCentral 2481
FDA SRS Y45QSO73OB
Human Metabolome Database HMDB0015214
Guide to Pharmacology 10923
KEGG C00413
PDB SRY
PharmGKB PA451512
PubChem 19649
SureChEMBL SCHEMBL3276
ZINC ZINC000008214681
CONTENTS