Basic Info

Common NameValidamycin(F05653)
2D Structure
FRCD IDF05653
CAS Number37248-47-8
PubChem CID443629
FormulaC20H35NO13
IUPAC Name

(2R,3R,4S,5S,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

InChI Key

JARYYMUOCXVXNK-CSLFJTBJSA-N

InChI

InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1

Canonical SMILES

C1C(C(C(C(C1NC2C=C(C(C(C2O)O)O)CO)O)O)OC3C(C(C(C(O3)CO)O)O)O)CO

Isomeric SMILES

C1[C@@H]([C@H]([C@@H]([C@H]([C@H]1N[C@H]2C=C([C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO

Synonyms
        
            Validamycin
        
            UNII-313E9620QS
        
            VALIDAMYCIN A
        
            37248-47-8
        
            jinggangmycin
        
            Validacin
        
            Valimon
        
            T-7545-A
        
            CHEBI:29703
        
            313E9620QS
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesGlycosyl compounds
Direct ParentO-glycosyl compounds
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsHexose monosaccharide - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Cyclitol or derivatives - Monosaccharide - Oxane - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Polyol - Secondary amine - Organoheterocyclic compound - Acetal - Oxacycle - Secondary aliphatic amine - Alcohol - Organopnictogen compound - Hydrocarbon derivative - Organic nitrogen compound - Amine - Primary alcohol - Organonitrogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Properties

Property NameProperty Value
Molecular Weight497.494
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Complexity697
Monoisotopic Mass497.211
Exact Mass497.211
XLogP-6.3
Formal Charge0
Heavy Atom Count34
Defined Atom Stereocenter Count14
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-0.9757
Human Intestinal AbsorptionHIA-0.8537
Caco-2 PermeabilityCaco2-0.7229
P-glycoprotein SubstrateSubstrate0.5642
P-glycoprotein InhibitorNon-inhibitor0.5321
Non-inhibitor0.8086
Renal Organic Cation TransporterNon-inhibitor0.8252
Distribution
Subcellular localizationLysosome0.3608
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7933
CYP450 2D6 SubstrateNon-substrate0.8504
CYP450 3A4 SubstrateNon-substrate0.5718
CYP450 1A2 InhibitorNon-inhibitor0.8702
CYP450 2C9 InhibitorNon-inhibitor0.8842
CYP450 2D6 InhibitorNon-inhibitor0.8856
CYP450 2C19 InhibitorNon-inhibitor0.8581
CYP450 3A4 InhibitorNon-inhibitor0.9764
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8251
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8603
Non-inhibitor0.8149
AMES ToxicityNon AMES toxic0.8354
CarcinogensNon-carcinogens0.9658
Fish ToxicityLow FHMT0.6959
Tetrahymena Pyriformis ToxicityLow TPT0.5579
Honey Bee ToxicityHigh HBT0.5601
BiodegradationReady biodegradable0.7770
Acute Oral ToxicityIV0.5170
Carcinogenicity (Three-class)Non-required0.6908

Model Value Unit
Absorption
Aqueous solubility-1.2705LogS
Caco-2 Permeability-0.5804LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6320LD50, mol/kg
Fish Toxicity1.5567pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0461pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Unshu Orange,PulpJapan0.05ppm
Other Composite VegetablesJapan0.05ppm
Other VegetablesJapan0.05ppm
Green SoybeansJapan0.05ppm
GingerJapan0.05ppm
Other Cucurbitaceous VegetablesJapan0.05ppm
Cucumber(Including Gherkin)Japan0.05ppm
Egg PlantJapan0.05ppm
TomatoJapan0.05ppm
Other Umbelliferous VegetablesJapan0.05ppm
MitsubaJapan0.05ppm
CeleryJapan0.05ppm
CarrotJapan0.05ppm
AsparagusJapan0.05ppm
NiraJapan0.05ppm
GarlicJapan0.05ppm
Welsh(Including Leek)Japan0.05ppm
OnionJapan0.05ppm
Lettuce(Including Cos Lettuce And Leaf Lettuce)Japan0.05ppm
EndiveJapan0.05ppm

References

TitleJournalDatePubmed ID
Determination of the antibiotic fungicide validamycin A in formulated products by micellar electrokinetic chromatography.J Agric Food Chem1999 Sep10552712