Novobiocin

Basic Info

Common NameNovobiocin(F05785)
2D Structure
FRCD IDF05785
CAS Number
PubChem CID54675769
FormulaC31H36N2O11
IUPAC Name

[(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] carbamate

InChI Key

YJQPYGGHQPGBLI-KGSXXDOSSA-N

InChI

InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1

Canonical SMILES

CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)OC4C(C(C(C(O4)(C)C)OC)OC(=O)N)O

Isomeric SMILES

CC1=C(C=CC2=C1OC(=O)C(=C2O)NC(=O)C3=CC(=C(C=C3)O)CC=C(C)C)O[C@H]4[C@@H]([C@@H]([C@H](C(O4)(C)C)OC)OC(=O)N)O

Synonyms
        
            Cardelmycin
        
            novobiocin
        
            Streptonivicin
        
            Inamycin
        
            Spheromycin
        
            Albamycin
        
            Cathomycin
        
            Crystallinic acid
        
            Novobiocina
        
            Novobiocine
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
SubclassCoumarin glycosides
Intermediate Tree NodesNot available
Direct ParentCoumarin glycosides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsCoumarin-7-o-glycoside - Coumarin o-glycoside - Phenolic glycoside - 4-hydroxycoumarin - Hydroxycoumarin - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Benzopyran - 1-benzopyran - Benzamide - Benzoic acid or derivatives - Benzoyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Pyran - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - Heteroaromatic compound - Vinylogous acid - Carbamic acid ester - Carboxamide group - Secondary carboxylic acid amide - Secondary alcohol - Lactone - Carbonic acid derivative - Ether - Dialkyl ether - Acetal - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Alcohol - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Properties

Property NameProperty Value
Molecular Weight612.632
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count11
Rotatable Bond Count9
Complexity1150
Monoisotopic Mass612.232
Exact Mass612.232
XLogP3.3
Formal Charge0
Heavy Atom Count44
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-0.9659
Human Intestinal AbsorptionHIA+0.6404
Caco-2 PermeabilityCaco2-0.6540
P-glycoprotein SubstrateSubstrate0.7897
P-glycoprotein InhibitorNon-inhibitor0.5095
Non-inhibitor0.6330
Renal Organic Cation TransporterNon-inhibitor0.9687
Distribution
Subcellular localizationMitochondria0.4483
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8342
CYP450 2D6 SubstrateNon-substrate0.8536
CYP450 3A4 SubstrateSubstrate0.5931
CYP450 1A2 InhibitorNon-inhibitor0.8072
CYP450 2C9 InhibitorNon-inhibitor0.7263
CYP450 2D6 InhibitorNon-inhibitor0.8720
CYP450 2C19 InhibitorNon-inhibitor0.7331
CYP450 3A4 InhibitorNon-inhibitor0.7934
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7844
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9935
Non-inhibitor0.9159
AMES ToxicityNon AMES toxic0.5713
CarcinogensNon-carcinogens0.9321
Fish ToxicityHigh FHMT0.9868
Tetrahymena Pyriformis ToxicityHigh TPT0.9843
Honey Bee ToxicityHigh HBT0.5417
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7684
Carcinogenicity (Three-class)Non-required0.6025
Model Value Unit
Absorption
Aqueous solubility-3.9119LogS
Caco-2 Permeability0.2702LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2899LD50, mol/kg
Fish Toxicity0.4685pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6823pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Edible Tissues Of DucksUnited States1ppm
Edible Tissues Of ChickensUnited States1ppm
Edible Tissues Of CattleUnited States1ppm
Milk From Dairy AnimalsUnited States0.1ppm
PerciformesJapan0.05ppm
Other Poultry Animals,Edible OffalJapan1ppm
Chicken,Edible OffalJapan0.05ppm
Other Poultry Animals,KidneyJapan1ppm
Chicken,KidneyJapan0.05ppm
Other Poultry Animals,LiverJapan1ppm
Chicken,LiverJapan0.05ppm
Other Poultry Animals,FatJapan1ppm
Chicken,FatJapan1ppm
Other Poultry Animals,MuscleJapan1ppm
Chicken,MuscleJapan0.05ppm
MilkJapan0.08ppm
Cattle,Edible OffalJapan0.7ppm
Cattle,KidneyJapan0.7ppm
Cattle,LiverJapan0.7ppm
Cattle,FatJapan1ppm

References

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Whole-Genome Sequencing and Genetic Analysis Reveal Novel Stress Responses toIndividual Constituents of Essential Oils in Escherichia coli.Appl Environ Microbiol2018 Mar 1929374037
Molecular Analysis, Biochemical Characterization, Antimicrobial Activity, andImmunological Analysis of Proteus mirabilis Isolated from Broilers.J Food Sci2018 Mar29437227
Detection of Shiga toxin-producing Escherichia coli (STEC) in ground beef and bean sprouts: Evaluation of culture enrichment conditions.Food Res Int2018 Jan29389629
Influence of Stress Factors Related to Cheese-Making Process and to STEC Detection Procedure on the Induction of Stx Phages from STEC O26:H11.Front Microbiol201728316592
Effects of different media on the enrichment of low numbers of Shiga toxin-producing Escherichia coli in mung bean sprouts and on the development of the sprout microbiome.Int J Food Microbiol2016 Sep 227240217
Comparison of Assurance GDS(®) MPX ID for Top STEC with Reference Culture Methods for the Detection of E. coli Top 6 STEC; Direct Confirmation of Top 6 STEC from Isolation Plates and Determination of Equivalence of PickPen(®) and FSIS OctoMACS™ Concentration Protocols.J AOAC Int2016 Mar-Apr26997139
Improving the Enrichment and Plating Methods for Rapid Detection of Non-O157 Shiga Toxin-Producing Escherichia coli in Dairy Compost.J Food Prot2016 Mar26939651
Isolation of Shiga Toxin-Producing Escherichia coli from Ground Beef Using Multiple Combinations of Enrichment Broths and Selective Agars.Foodborne Pathog Dis2016 Mar26836701
Comparison of Agar Media for Detection and Quantification of Shiga Toxin-Producing Escherichia coli in Cattle Feces.J Food Prot2016 Jun27296597
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Detection, enumeration and characterization of Yersinia enterocolitica 4/O:3 in pig tonsils at slaughter in Northern Italy.Int J Food Microbiol2014 May 224598512
Construction and characterization of an Escherichia coli mutant producing Kdo₂-lipid A.Mar Drugs2014 Mar 1324633251
Evaluation of a multiplex real-time PCR method for detecting shiga toxin-producing Escherichia coli in beef and comparison to the U.S. Department of Agriculture Food Safety and Inspection Service Microbiology laboratory guidebook method.J Food Prot2014 Feb24490911
Detection of Shiga toxin-producing Escherichia coli (STEC) O157:H7, O26, O45, O103, O111, O121, and O145, and Salmonella in retail raw ground beef using the DuPont™ BAX® system.Front Cell Infect Microbiol201424995164
Isolation and characterization of new p-Terphenyls with antifungal,antibacterial, and antioxidant activities from halophilic actinomyceteNocardiopsis gilva YIM 90087.J Agric Food Chem2013 Mar 2723441911
A proposal to unify two subspecies of Staphylococcus equorum: Staphylococcusequorum subsp. equorum and Staphylococcus equorum subsp. linens.Antonie Van Leeuwenhoek2013 Dec24057981
Isolation of Shiga toxin-producing Escherichia coli serogroups O26, O45, O103, O111, O121, and O145 from ground beef using modified rainbow agar and post-immunomagnetic separation acid treatment.J Food Prot2012 Sep22947460
Application of a real-time PCR-based system for monitoring of O26, O103, O111, O145 and O157 Shiga toxin-producing Escherichia coli in cattle at slaughter.Zoonoses Public Health2012 Sep22348425
A combination of direct viable count and fluorescence in situ hybridization forspecific enumeration of viable Lactobacillus delbrueckii subsp.bulgaricus andStreptococcus thermophilus.Lett Appl Microbiol2012 Mar22188589
New role of antibody in bacterial isolation.J AOAC Int2012 Jan-Feb22468362