Streptomycin

Basic Info

Common NameStreptomycin(F05947)
2D Structure
FRCD IDF05947
CAS Number57-92-1
PubChem CID19649
FormulaC21H39N7O12
IUPAC Name

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

InChI Key

UCSJYZPVAKXKNQ-HZYVHMACSA-N

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

Canonical SMILES

CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(C=O)O

Isomeric SMILES

C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(C=O)O

Synonyms
        
            Streptomycin A
        
            Streptomycin sulfate
        
            streptomycin
        
            57-92-1
        
            Gerox
        
            Streptomycin sulphate
        
            Estreptomicina
        
            Agrimycin
        
            Strepcen
        
            Chemform
Classifies
                

                  
                    Veterinary Drug
                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides - Aminoglycosides
Direct ParentAminocyclitol glycosides
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsAmino cyclitol glycoside - Glycosyl compound - O-glycosyl compound - Cyclohexanol - Monosaccharide - Cyclitol or derivatives - Oxane - Cyclic alcohol - Tertiary alcohol - Tetrahydrofuran - 1,2-aminoalcohol - Secondary alcohol - Guanidine - Secondary amine - Secondary aliphatic amine - Polyol - Organic 1,3-dipolar compound - Organoheterocyclic compound - Oxacycle - Acetal - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organonitrogen compound - Primary alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Amine - Aldehyde - Alcohol - Organopnictogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight581.58
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count15
Rotatable Bond Count9
Complexity940
Monoisotopic Mass581.266
Exact Mass581.266
XLogP-8
Formal Charge0
Heavy Atom Count40
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9712
Human Intestinal AbsorptionHIA-0.8824
Caco-2 PermeabilityCaco2-0.6968
P-glycoprotein SubstrateSubstrate0.5531
P-glycoprotein InhibitorNon-inhibitor0.7577
Non-inhibitor0.8382
Renal Organic Cation TransporterNon-inhibitor0.7782
Distribution
Subcellular localizationLysosome0.4518
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7053
CYP450 2D6 SubstrateNon-substrate0.8177
CYP450 3A4 SubstrateNon-substrate0.5275
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9072
CYP450 2D6 InhibitorNon-inhibitor0.9230
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8867
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8818
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9924
Non-inhibitor0.9009
AMES ToxicityAMES toxic0.9107
CarcinogensNon-carcinogens0.9528
Fish ToxicityLow FHMT0.7366
Tetrahymena Pyriformis ToxicityHigh TPT0.9400
Honey Bee ToxicityLow HBT0.5908
BiodegradationNot ready biodegradable0.9821
Acute Oral ToxicityIV0.6171
Carcinogenicity (Three-class)Non-required0.5741
Model Value Unit
Absorption
Aqueous solubility-2.0122LogS
Caco-2 Permeability-0.5128LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8409LD50, mol/kg
Fish Toxicity1.5640pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2635pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muscle1011010European Union0.526/04/2017
Fat1011020European Union0.526/04/2017
Liver1011030European Union0.526/04/2017
Kidney1011040European Union126/04/2017
Muscle1012010European Union0.526/04/2017
Fat1012020European Union0.526/04/2017
Liver1012030European Union0.526/04/2017
Kidney1012040European Union126/04/2017
Muscle1013010European Union0.526/04/2017
Fat1013020European Union0.526/04/2017
Liver1013030European Union0.526/04/2017
Kidney1013040European Union126/04/2017
Muscle1014010European Union0.526/04/2017
Fat1014020European Union0.526/04/2017
Liver1014030European Union0.526/04/2017
Kidney1014040European Union126/04/2017
Muscle1017010European Union0.526/04/2017
Fat1017020European Union0.526/04/2017
Liver1017030European Union0.526/04/2017
Kidney1017040European Union126/04/2017

References

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