Basic Info

Common NameDestomycin A(F06029)
2D Structure
FRCD IDF06029
CAS Number14918-35-5
PubChem CID502206
FormulaC20H37N3O13
IUPAC Name

(3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-[(1S,2R,3S,5R,6S)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-[(1S)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol

InChI Key

GRRNUXAQVGOGFE-SVNOMHMPSA-N

InChI

InChI=1S/C20H37N3O13/c1-23-7-2-5(21)9(26)15(10(7)27)33-19-17-16(11(28)8(4-25)32-19)35-20(36-17)18(31)13(30)12(29)14(34-20)6(22)3-24/h5-19,23-31H,2-4,21-22H2,1H3/t5-,6-,7+,8+,9+,10-,11-,12+,13-,14+,15-,16-,17-,18+,19-,20?/m0/s1

Canonical SMILES

CNC1CC(C(C(C1O)OC2C3C(C(C(O2)CO)O)OC4(O3)C(C(C(C(O4)C(CO)N)O)O)O)O)N

Isomeric SMILES

CN[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O)O[C@H]2[C@@H]3[C@H]([C@H]([C@H](O2)CO)O)OC4(O3)[C@@H]([C@H]([C@H]([C@H](O4)[C@H](CO)N)O)O)O)O)N

Synonyms
        
            (3'R,3aS,4S,4'S,5'R,6R,6'R,7S,7aS)-4-[(1S,2R,3S,5R,6S)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexoxy]-6'-[(1S)-1-amino-2-hydroxy-ethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,2'-tetrahydropyran]-3',4',5',7-tetrol
        
            Destomycin A
        
            Destomysin
        
            14918-35-5
        
            Destonate 20
        
            AC1L9W0F
        
            NSC96877
        
            C01688
        
            NSC 96877
        
            2,3-O-(6-(1-Amino-2-hydroxyethyl)-3,4,5-trihydroxytetrahydropyran-2-yliden)-(3-amino-5-methylamino-3,4,5-tridesoxy-mesoinosit-1-yl)-beta-D-talopyranosid
        
Classifies
                

                  
                    Predicted: Pesticide
                  

                
        
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
Direct Parent2-deoxystreptamine aminoglycosides
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
Substituents2-deoxystreptamine aminoglycoside - Disaccharide - Glycosyl compound - O-glycosyl compound - Dioxolopyran - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Carboxylic acid orthoester - Ortho ester - Cyclitol or derivatives - Oxane - Cyclic alcohol - Meta-dioxolane - Orthocarboxylic acid derivative - 1,2-aminoalcohol - Secondary alcohol - Secondary amine - Organoheterocyclic compound - Oxacycle - Acetal - Secondary aliphatic amine - Polyol - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Primary alcohol - Primary amine - Amine - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 2-deoxystreptamine aminoglycosides. These are aminoglycosides containing the 2-deoxystreptamine (1,3-diaminocyclohexane-4,5,6-triol) core.

Properties

Property NameProperty Value
Molecular Weight527.524
Hydrogen Bond Donor Count11
Hydrogen Bond Acceptor Count16
Rotatable Bond Count6
Complexity756
Monoisotopic Mass527.233
Exact Mass527.233
XLogP-6.6
Formal Charge0
Heavy Atom Count36
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9783
Human Intestinal AbsorptionHIA-0.5442
Caco-2 PermeabilityCaco2-0.7045
P-glycoprotein SubstrateSubstrate0.6604
P-glycoprotein InhibitorNon-inhibitor0.7855
Non-inhibitor0.9781
Renal Organic Cation TransporterNon-inhibitor0.8392
Distribution
Subcellular localizationLysosome0.6336
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7694
CYP450 2D6 SubstrateNon-substrate0.7885
CYP450 3A4 SubstrateNon-substrate0.5122
CYP450 1A2 InhibitorNon-inhibitor0.8822
CYP450 2C9 InhibitorNon-inhibitor0.9023
CYP450 2D6 InhibitorNon-inhibitor0.8976
CYP450 2C19 InhibitorNon-inhibitor0.8641
CYP450 3A4 InhibitorNon-inhibitor0.9267
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8175
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9744
Non-inhibitor0.8257
AMES ToxicityNon AMES toxic0.5424
CarcinogensNon-carcinogens0.9612
Fish ToxicityHigh FHMT0.6484
Tetrahymena Pyriformis ToxicityHigh TPT0.7302
Honey Bee ToxicityHigh HBT0.5140
BiodegradationNot ready biodegradable0.9851
Acute Oral ToxicityI0.8269
Carcinogenicity (Three-class)Non-required0.5854

Model Value Unit
Absorption
Aqueous solubility-1.8845LogS
Caco-2 Permeability-0.5240LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.8668LD50, mol/kg
Fish Toxicity1.6945pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1106pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pig,Edible OffalJapan0.5ppm
Pig,KidneyJapan0.5ppm
Pig,LiverJapan0.5ppm
Pig,FatJapan0.5ppm
Pig,MuscleJapan0.5ppm