Kasugamycin

Basic Info

Common NameKasugamycin(F05895)
2D Structure
FRCD IDF05895
CAS Number6980-18-3
PubChem CID65174
FormulaC14H25N3O9
IUPAC Name

2-amino-2-[(2R,3S,5S,6R)-5-amino-2-methyl-6-[(2S,3S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]iminoacetic acid

InChI Key

PVTHJAPFENJVNC-UQTMRZPGSA-N

InChI

InChI=1S/C14H25N3O9/c1-3-5(17-12(16)13(23)24)2-4(15)14(25-3)26-11-9(21)7(19)6(18)8(20)10(11)22/h3-11,14,18-22H,2,15H2,1H3,(H2,16,17)(H,23,24)/t3-,4+,5+,6?,7+,8+,9-,10+,11?,14-/m1/s1

Canonical SMILES

CC1C(CC(C(O1)OC2C(C(C(C(C2O)O)O)O)O)N)N=C(C(=O)O)N

Isomeric SMILES

C[C@@H]1[C@H](C[C@@H]([C@H](O1)OC2[C@@H]([C@H](C([C@@H]([C@@H]2O)O)O)O)O)N)N=C(C(=O)O)N

Synonyms
        
            KASUGAMYCIN
        
            Kasuminl
        
            6980-18-3
        
            Kasumin L
        
            Kasumin 2L
        
            UNII-O957UYB9DY
        
            HSDB 6695
        
            BRN 1403823
        
            O957UYB9DY
        
            CHEBI:81419
Classifies
                

                  
                    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 - Alpha-amino acid or derivatives - Cyclohexanol - Cyclitol or derivatives - Monosaccharide - Oxane - Cyclic alcohol - Amino acid or derivatives - Amino acid - Secondary alcohol - Acetal - Amidine - Carboxylic acid amidine - Carboxylic acid derivative - Carboxylic acid - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Polyol - Carboximidamide - Alcohol - Amine - Organopnictogen compound - Primary aliphatic amine - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Carbonyl group - Primary amine - Organic nitrogen 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 Weight379.366
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Complexity532
Monoisotopic Mass379.159
Exact Mass379.159
XLogP-6.7
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count8
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-0.9215
Human Intestinal AbsorptionHIA-0.7660
Caco-2 PermeabilityCaco2-0.7006
P-glycoprotein SubstrateSubstrate0.6995
P-glycoprotein InhibitorNon-inhibitor0.8843
Non-inhibitor0.8792
Renal Organic Cation TransporterNon-inhibitor0.8428
Distribution
Subcellular localizationLysosome0.5542
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6068
CYP450 2D6 SubstrateNon-substrate0.8376
CYP450 3A4 SubstrateNon-substrate0.6082
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8374
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8728
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9961
Non-inhibitor0.9346
AMES ToxicityNon AMES toxic0.6374
CarcinogensNon-carcinogens0.9118
Fish ToxicityLow FHMT0.7839
Tetrahymena Pyriformis ToxicityHigh TPT0.8206
Honey Bee ToxicityLow HBT0.7180
BiodegradationNot ready biodegradable0.8326
Acute Oral ToxicityIV0.6120
Carcinogenicity (Three-class)Non-required0.6751
Model Value Unit
Absorption
Aqueous solubility-2.1271LogS
Caco-2 Permeability-0.6734LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5530LD50, mol/kg
Fish Toxicity1.6011pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3187pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other HerbsJapan0.05ppm
Other SpicesJapan0.05ppm
TeaJapan0.04ppm
Other FruitsJapan0.05ppm
KiwifruitJapan0.04ppm
Mume PlumJapan0.04ppm
PeachJapan0.04ppm
LoquatJapan0.04ppm
PearJapan0.04ppm
Japanese PearJapan0.04ppm
Other Citrus FruitsJapan0.05ppm
LimeJapan0.05ppm
GrapefruitJapan0.05ppm
Orange(Including Navel Orange)Japan0.05ppm
LemonJapan0.05ppm
Citrus Natsudaidai,WholeJapan0.05ppm
Unshu Orange,PulpJapan0.05ppm
Other VegetablesJapan0.05ppm
GingerJapan0.05ppm
OkraJapan0.05ppm

References

TitleJournalDatePubmed ID
Simultaneous determination of kasugamycin and validamycin-A residues in cerealsby consecutive solid-phase extraction combined with liquid chromatography-tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Mar29210618
Multi-residue analysis of pesticides, plant hormones, veterinary drugs and mycotoxins using HILIC chromatography - MS/MS in various food matrices.Anal Chim Acta2016 Oct 2627720116
Synthesis, characterization, and application of microbe-triggeredcontrolled-release kasugamycin-pectin conjugate.J Agric Food Chem2015 May 625876441
Simultaneous determination of 15 aminoglycoside(s) residues in animal derivedfoods by automated solid-phase extraction and liquid chromatography-tandem massspectrometry.Food Chem2012 Nov 1522868145
Inactivation of KsgA, a 16S rRNA methyltransferase, causes vigorous emergence of mutants with high-level kasugamycin resistance.Antimicrob Agents Chemother2009 Jan19001112
[Techniques of diseases, insect pests and weeds control and their efficacy inbio-rational rice production].Ying Yong Sheng Tai Xue Bao2004 Jan15139200