Paromomycin

Basic Info

Common NameParomomycin(F05735)
2D Structure
FRCD IDF05735
CAS Number7542-37-2
PubChem CID165580
FormulaC23H45N5O14
IUPAC Name

(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol

InChI Key

UOZODPSAJZTQNH-LSWIJEOBSA-N

InChI

InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

Canonical SMILES

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N

Isomeric SMILES

C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N

Synonyms
        
            Paramomycin Sulfate
        
            paromomycin
        
            Aminosidin
        
            AMINOSIDINE
        
            Paromomycin I
        
            Neomycin E
        
            7542-37-2
        
            Paromomicina
        
            Paromomycinum
        
            catenulin
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides - Aminoglycosides - Aminocyclitol glycosides - 2-deoxystreptamine aminoglycosides
Direct Parent4,5-disubstituted 2-deoxystreptamines
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
Substituents4,5-disubstituted 2-deoxystreptamine - Disaccharide - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Cyclitol or derivatives - Oxane - Tetrahydrofuran - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Acetal - Organoheterocyclic compound - Oxacycle - Primary alcohol - Hydrocarbon derivative - Organopnictogen compound - Primary aliphatic amine - Organonitrogen compound - Organic nitrogen compound - Amine - Alcohol - Primary amine - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.

Properties

Property NameProperty Value
Molecular Weight615.634
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count19
Rotatable Bond Count9
Complexity870
Monoisotopic Mass615.296
Exact Mass615.296
XLogP-8.7
Formal Charge0
Heavy Atom Count42
Defined Atom Stereocenter Count19
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-0.9659
Human Intestinal AbsorptionHIA-0.8617
Caco-2 PermeabilityCaco2-0.7502
P-glycoprotein SubstrateNon-substrate0.5164
P-glycoprotein InhibitorNon-inhibitor0.8023
Non-inhibitor0.8764
Renal Organic Cation TransporterNon-inhibitor0.7886
Distribution
Subcellular localizationLysosome0.5216
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8231
CYP450 2D6 SubstrateNon-substrate0.8041
CYP450 3A4 SubstrateNon-substrate0.6473
CYP450 1A2 InhibitorNon-inhibitor0.9157
CYP450 2C9 InhibitorNon-inhibitor0.9147
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9034
CYP450 3A4 InhibitorNon-inhibitor0.9471
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8446
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9728
Non-inhibitor0.8100
AMES ToxicityNon AMES toxic0.6934
CarcinogensNon-carcinogens0.9505
Fish ToxicityLow FHMT0.6900
Tetrahymena Pyriformis ToxicityLow TPT0.6477
Honey Bee ToxicityLow HBT0.6385
BiodegradationNot ready biodegradable0.8587
Acute Oral ToxicityIV0.6098
Carcinogenicity (Three-class)Non-required0.6540
Model Value Unit
Absorption
Aqueous solubility-0.6772LogS
Caco-2 Permeability-0.4162LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4850LD50, mol/kg
Fish Toxicity1.9649pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0594pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
SalmoniformesJapan0.5ppm
Other Terrestrial Mammals,LiverJapan2ppm
Other Terrestrial Mammals,Edible OffalJapan2ppm
Other Aquatic AnimalJapan0.5ppm
CrustaceansJapan0.5ppm
Shelled MolluscasJapan0.5ppm
Other FishJapan0.5ppm
PerciformesJapan0.5ppm
AnguilliformesJapan0.5ppm
Other Poultry Animals,Edible OffalJapan2ppm
Chicken,Edible OffalJapan2ppm
Other Poultry Animals,KidneyJapan2ppm
Chicken,KidneyJapan2ppm
Other Poultry Animals,LiverJapan2ppm
Chicken,LiverJapan2ppm
Other Poultry Animals,FatJapan0.5ppm
Chicken,FatJapan0.5ppm
Other Poultry Animals,MuscleJapan0.5ppm
Chicken,MuscleJapan0.5ppm
Pig,Edible OffalJapan2ppm

References

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A model for endosymbiosis: interaction between Tetrahymena pyriformis and Escherichia coli.Eur J Protistol2013 Nov23763905
Development of an efficient transformation method by Agrobacterium tumefaciensand high throughput spray assay to identify transgenic plants for woodlandstrawberry (Fragaria vesca) using NPTII selection.Plant Cell Rep2013 Mar23160638
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