Basic Info

Common NameOleandomycin(F05844)
2D Structure
FRCD IDF05844
CAS Number3922-90-5
PubChem CID72493
FormulaC35H61NO12
IUPAC Name

(3R,5S,6S,7R,8S,9R,12R,13R,14S,15R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-1,11-dioxaspiro[2.13]hexadecane-10,16-dione

InChI Key

RZPAKFUAFGMUPI-QESOVKLGSA-N

InChI

InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1

Canonical SMILES

CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C

Isomeric SMILES

C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C

Synonyms
        
            Oleandomycin A
        
            oleandomycin
        
            Landomycin
        
            Matromycin
        
            Amimycin
        
            Romicil
        
            3922-90-5
        
            CHEBI:16869
        
            UNII-P8ZQ646136
        
            P8ZQ646136
        
Classifies
                

                  
                    Veterinary Drug
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsAminoglycoside core - Macrolide - Glycosyl compound - O-glycosyl compound - Monosaccharide - Oxane - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Ketone - Lactone - Secondary alcohol - Tertiary amine - Tertiary aliphatic amine - Acetal - Organoheterocyclic compound - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Dialkyl ether - Oxirane - Ether - Organonitrogen compound - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic nitrogen compound - Organopnictogen compound - Amine - Organic oxide - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Properties

Property NameProperty Value
Molecular Weight687.868
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count13
Rotatable Bond Count6
Complexity1090
Monoisotopic Mass687.419
Exact Mass687.419
XLogP2.6
Formal Charge0
Heavy Atom Count48
Defined Atom Stereocenter Count18
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-0.9923
Human Intestinal AbsorptionHIA+0.7173
Caco-2 PermeabilityCaco2-0.6499
P-glycoprotein SubstrateSubstrate0.7589
P-glycoprotein InhibitorInhibitor0.7890
Non-inhibitor0.6658
Renal Organic Cation TransporterNon-inhibitor0.8605
Distribution
Subcellular localizationLysosome0.4323
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8004
CYP450 2D6 SubstrateNon-substrate0.9031
CYP450 3A4 SubstrateSubstrate0.6984
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9291
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.5537
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9629
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9931
Non-inhibitor0.8978
AMES ToxicityNon AMES toxic0.5307
CarcinogensNon-carcinogens0.9182
Fish ToxicityHigh FHMT0.7059
Tetrahymena Pyriformis ToxicityHigh TPT0.7871
Honey Bee ToxicityLow HBT0.5000
BiodegradationNot ready biodegradable0.9968
Acute Oral ToxicityIV0.6828
Carcinogenicity (Three-class)Non-required0.5365

Model Value Unit
Absorption
Aqueous solubility-2.5809LogS
Caco-2 Permeability0.8888LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0423LD50, mol/kg
Fish Toxicity1.3050pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4980pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,Edible OffalJapan0.2ppm
Other Poultry Animals,KidneyJapan0.2ppm
Chicken,KidneyJapan0.2ppm
Other Poultry Animals,LiverJapan0.2ppm
Chicken,LiverJapan0.2ppm
Other Poultry Animals,FatJapan0.2ppm
Chicken,FatJapan0.2ppm
Other Poultry Animals,MuscleJapan0.2ppm
Chicken,MuscleJapan0.2ppm
MilkJapan0.05ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Other Poultry Animals,Edible OffalJapan0.2ppm
Pig,Edible OffalJapan0.1ppm
Edible Tissues Of SwineUnited States0.15ppm
Edible Tissues Of TurkeysUnited States0.15ppm
Edible Tissues Of ChickensUnited States0.15ppm
PerciformesJapan0.05ppm