Basic Info

Common NameBicozamycin(F05675)
2D Structure
FRCD IDF05675
CAS Number
PubChem CID65807
FormulaC12H18N2O7
IUPAC Name

(1R,6S)-1-hydroxy-2-methylidene-6-[(1S,2S)-1,2,3-trihydroxy-2-methylpropyl]-5-oxa-8,10-diazabicyclo[4.2.2]decane-7,9-dione

InChI Key

WOUDXEYYJPOSNE-VKZDFBPFSA-N

InChI

InChI=1S/C12H18N2O7/c1-6-3-4-21-12(7(16)10(2,19)5-15)9(18)13-11(6,20)8(17)14-12/h7,15-16,19-20H,1,3-5H2,2H3,(H,13,18)(H,14,17)/t7-,10-,11+,12-/m0/s1

Canonical SMILES

CC(CO)(C(C12C(=O)NC(C(=C)CCO1)(C(=O)N2)O)O)O

Isomeric SMILES

C[C@](CO)([C@@H]([C@@]12C(=O)N[C@@](C(=C)CCO1)(C(=O)N2)O)O)O

Synonyms
        
            Bicozamicina
        
            Bicozamycin [INN]
        
            Bicyclomycin
        
            Bicozamycin
        
            Aizumycin
        
            Bacteron
        
            Bicozamycine
        
            Bicozamycinum
        
            Bacfeed
        
            Antibiotic 5879
        
Classifies
                

                  
                    Predicted: Fungal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassAlcohols and polyols
Intermediate Tree NodesNot available
Direct ParentTertiary alcohols
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsTertiary alcohol - Cyclic carboximidic acid - Secondary alcohol - Alkanolamine - Polyol - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Azacycle - Oxacycle - Organonitrogen compound - Hydrocarbon derivative - Primary alcohol - Organic nitrogen compound - Organopnictogen compound - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as tertiary alcohols. These are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Properties

Property NameProperty Value
Molecular Weight302.283
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Complexity510
Monoisotopic Mass302.111
Exact Mass302.111
XLogP-2.9
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count4
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-0.7744
Human Intestinal AbsorptionHIA-0.7945
Caco-2 PermeabilityCaco2-0.7146
P-glycoprotein SubstrateSubstrate0.8454
P-glycoprotein InhibitorNon-inhibitor0.7955
Non-inhibitor0.9955
Renal Organic Cation TransporterNon-inhibitor0.9455
Distribution
Subcellular localizationMitochondria0.5627
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8728
CYP450 2D6 SubstrateNon-substrate0.8073
CYP450 3A4 SubstrateNon-substrate0.5295
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9321
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.9385
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9728
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9804
Non-inhibitor0.9035
AMES ToxicityNon AMES toxic0.5323
CarcinogensNon-carcinogens0.9594
Fish ToxicityLow FHMT0.6442
Tetrahymena Pyriformis ToxicityHigh TPT0.8155
Honey Bee ToxicityLow HBT0.5971
BiodegradationNot ready biodegradable0.9725
Acute Oral ToxicityIII0.5772
Carcinogenicity (Three-class)Non-required0.6078

Model Value Unit
Absorption
Aqueous solubility-1.8511LogS
Caco-2 Permeability-0.1328LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4981LD50, mol/kg
Fish Toxicity1.6769pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1544pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PerciformesJapan0.05ppm
Chicken,KidneyJapan0.05ppm
Chicken,LiverJapan0.05ppm
Chicken,FatJapan0.05ppm
Chicken,MuscleJapan0.05ppm
MilkJapan0.1ppm
Pig,Edible OffalJapan0.2ppm
Cattle,Edible OffalJapan0.3ppm
Pig,KidneyJapan0.2ppm
Cattle,KidneyJapan0.2ppm
Pig,LiverJapan0.2ppm
Cattle,LiverJapan0.2ppm
Pig,FatJapan0.05ppm
Cattle,FatJapan0.05ppm
Pig,MuscleJapan0.2ppm
Cattle,MuscleJapan0.2ppm
Chicken,Edible OffalJapan0.05ppm

References

TitleJournalDatePubmed ID
Multivariable Analysis of the Association Between Antimicrobial Use andAntimicrobial Resistance in Escherichia coli Isolated from Apparently HealthyPigs in Japan.Microb Drug Resist2016 Jan26296068
Prevalence of Salmonella isolates and antimicrobial resistance patterns inchicken meat throughout Japan.J Food Prot2011 Feb21333147
Relationships between multidrug-resistant Salmonella enterica SerovarSchwarzengrund and both broiler chickens and retail chicken meats in Japan.Jpn J Infect Dis2009 May19468180
National surveillance of Salmonella enterica in food-producing animals in Japan.Acta Vet Scand2009 Aug 2519703311
[Determination of bicozamycin in livestock products and seafoods by liquidchromatography-tandem mass spectrometry].Shokuhin Eiseigaku Zasshi2009 Apr19436151
Prevention and treatment of traveler's diarrhea: a clinical pharmacologicalapproach.Chemotherapy19957671647