Dihydrostreptomycin sulfate (CHEM018579)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:21:20 UTC
Update Date2016-11-09 01:15:49 UTC
Accession NumberCHEM018579
Identification
Common NameDihydrostreptomycin sulfate
ClassSmall Molecule
DescriptionDihydrostreptomycin is a derivative of streptomycin that has a bactericidal properties. It is a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.It acts by irreversibly binding the S12 protein in the bacterial 30S ribosomal subunit, after being actively transported across the cell membrane, which interferes with the initiation complex between the mRNA and the bacterial ribosome. This leads to the synthesis of defective non-functional proteins, which results in the bacterial cell's death.It causes ototoxicity, which is why it is no longer used in humans.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Dihydrostreptomycin sulfuric acidGenerator
Dihydrostreptomycin sulphateGenerator
Dihydrostreptomycin sulphuric acidGenerator
Sulfate, dihydrostreptomycinMeSH
CitrocilMeSH
DihydrostreptomycinMeSH
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;sulfateGenerator
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;sulphateGenerator
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;sulphuric acidGenerator
Dihydrostreptomycin sulfateMeSH
instituto Farmacologica brand OF dihydrostreptomycin sulfateMeSH
Chemical FormulaC42H88N14O36S3
Average Molecular Mass1461.410 g/mol
Monoisotopic Mass1460.465 g/mol
CAS Registry Number5490-27-7
IUPAC Namebis(N-[(1R,2R,3S,4R,5R,6S)-3-carbamimidamido-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); tris(sulfuric acid)
Traditional Namebis(dihydrostreptomycin); tris(sulfuric acid)
SMILESOS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.[H][C@@]1(C)O[C@@]([H])(O[C@@]2([H])[C@]([H])(O)[C@@]([H])(O)[C@]([H])(NC(N)=N)[C@@]([H])(O)[C@]2([H])NC(N)=N)[C@]([H])(O[C@]2([H])O[C@@]([H])(CO)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])NC)[C@@]1(O)CO.[H][C@@]1(C)O[C@@]([H])(O[C@@]2([H])[C@]([H])(O)[C@@]([H])(O)[C@]([H])(NC(N)=N)[C@@]([H])(O)[C@]2([H])NC(N)=N)[C@]([H])(O[C@]2([H])O[C@@]([H])(CO)[C@]([H])(O)[C@@]([H])(O)[C@]2([H])NC)[C@@]1(O)CO
InChI IdentifierInChI=1S/2C21H41N7O12.3H2O4S/c2*1-5-21(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;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;;/m00.../s1
InChI KeyCZWJCQXZZJHHRH-YCRXJPFRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminocyclitol glycosides
Alternative Parents
Substituents
  • Amino cyclitol glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Cyclohexanol
  • Cyclitol or derivatives
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Guanidine
  • Carboximidamide
  • Acetal
  • Secondary amine
  • Secondary aliphatic amine
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Amine
  • Primary alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16 g/LALOGPS
logP-3ALOGPS
logP-7.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)11.31ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area334.59 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity150.45 m³·mol⁻¹ChemAxon
Polarizability56.38 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-60b801c31e9e4d8d6cc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-60b801c31e9e4d8d6cc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000900000-60b801c31e9e4d8d6cc2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-ba387d007118a24f0c45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-ba387d007118a24f0c45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-ba387d007118a24f0c45Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDihydrostreptomycin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID21653
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available