Basic Info

Common NameFlavomycin(F06210)
2D Structure
FRCD IDF06210
CAS Number11015-37-5
PubChem CID46783781
FormulaC69H107N4O35P
IUPAC Name

(2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4-carbamoyloxy-6-[[(2R)-2-carboxy-2-[(2E,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]ethoxy]-hydroxyphosphoryl]oxy-3-hydroxy-3-methyloxane-2-carboxylic acid

InChI Key

PERZMHJGZKHNGU-XIGAONJHSA-N

InChI

InChI=1S/C69H107N4O35P/c1-30(2)15-14-17-31(3)18-19-33(5)22-25-68(9,10)24-13-12-16-32(4)23-26-96-41(60(88)89)29-98-109(94,95)108-66-56(57(107-67(70)92)69(11,93)58(106-66)61(90)91)105-63-44(72-36(8)76)47(81)54(40(101-63)28-97-64-51(85)48(82)45(79)39(27-74)100-64)103-62-43(71-35(7)75)46(80)53(34(6)99-62)102-65-52(86)49(83)50(84)55(104-65)59(87)73-42-37(77)20-21-38(42)78/h13,15,18,23-24,34,39-41,43-58,62-66,74,77,79-86,93H,5,12,14,16-17,19-22,25-29H2,1-4,6-11H3,(H2,70,92)(H,71,75)(H,72,76)(H,73,87)(H,88,89)(H,90,91)(H,94,95)/b24-13+,31-18+,32-23+/t34?,39-,40-,41-,43-,44-,45-,46-,47-,48+,49+,50-,51-,52-,53-,54-,55+,56-,57-,58-,62+,63+,64-,65-,66-,69+/m1/s1

Canonical SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)NC(=O)C)OC3C(C(C(OC3OP(=O)(O)OCC(C(=O)O)OCC=C(C)CCC=CC(C)(C)CCC(=C)CC=C(C)CCC=C(C)C)C(=O)O)(C)O)OC(=O)N)COC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)O)OC5C(C(C(C(O5)C(=O)NC6=C(CCC6=O)O)O)O)O

Isomeric SMILES

CC1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)NC(=O)C)O[C@@H]3[C@H]([C@]([C@H](O[C@@H]3OP(=O)(O)OC[C@H](C(=O)O)OC/C=C(\C)/CC/C=C/C(C)(C)CCC(=C)C/C=C(\C)/CCC=C(C)C)C(=O)O)(C)O)OC(=O)N)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)NC(=O)C)O)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)C(=O)NC6=C(CCC6=O)O)O)O)O

Synonyms
        
            (2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-
        
            Flavomycin
        
            11015-37-5
        
            Moenomycin complex
        
            MolPort-006-823-804
        
            C69H107N4O35P
        
            AKOS016339637
        
            KS-5173
        
            I020
        
            015F375
        
Classifies
                

                  
                    Predicted: Plant Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassTerpene glycosides
Intermediate Tree NodesNot available
Direct ParentTerpene glycosides
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsOligosaccharide phosphate - Oligosaccharide - Terpene glycoside - Fatty acyl glycoside - N-acyl-alpha-hexosamine - Glucuronic acid or derivatives - Glycosyl compound - O-glycosyl compound - Monocyclic monoterpenoid - Monoterpenoid - Glyceric_acid - Dialkyl phosphate - Alkyl phosphate - Dicarboxylic acid or derivatives - Pyran - Fatty acyl - Phosphoric acid ester - Oxane - Organic phosphoric acid derivative - Tertiary alcohol - Vinylogous acid - Cyclic ketone - Ketone - Secondary alcohol - Propargyl-type 1,3-dipolar organic compound - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Organic 1,3-dipolar compound - Ether - Acetal - Oxacycle - Organoheterocyclic compound - Polyol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Imine - Carbonyl group - Organic oxide - Hydrocarbon derivative - Alcohol - Primary alcohol - Aldehyde - Organooxygen compound - Organonitrogen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Properties

Property NameProperty Value
Molecular Weight1583.582
Hydrogen Bond Donor Count18
Hydrogen Bond Acceptor Count35
Rotatable Bond Count38
Complexity3370
Monoisotopic Mass1582.645
Exact Mass1582.645
XLogP-0.7
Formal Charge0
Heavy Atom Count109
Defined Atom Stereocenter Count25
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9264
Human Intestinal AbsorptionHIA-0.9810
Caco-2 PermeabilityCaco2-0.6654
P-glycoprotein SubstrateSubstrate0.7291
P-glycoprotein InhibitorInhibitor0.7255
Non-inhibitor0.8652
Renal Organic Cation TransporterNon-inhibitor0.9591
Distribution
Subcellular localizationMitochondria0.6217
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7909
CYP450 2D6 SubstrateNon-substrate0.8199
CYP450 3A4 SubstrateSubstrate0.6130
CYP450 1A2 InhibitorNon-inhibitor0.7619
CYP450 2C9 InhibitorNon-inhibitor0.7595
CYP450 2D6 InhibitorNon-inhibitor0.8819
CYP450 2C19 InhibitorNon-inhibitor0.7166
CYP450 3A4 InhibitorNon-inhibitor0.5635
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8611
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9419
Non-inhibitor0.7475
AMES ToxicityNon AMES toxic0.6318
CarcinogensNon-carcinogens0.9191
Fish ToxicityHigh FHMT0.9922
Tetrahymena Pyriformis ToxicityHigh TPT0.9917
Honey Bee ToxicityHigh HBT0.5285
BiodegradationNot ready biodegradable0.9805
Acute Oral ToxicityIII0.5840
Carcinogenicity (Three-class)Non-required0.5100

Model Value Unit
Absorption
Aqueous solubility-3.1970LogS
Caco-2 Permeability-0.3479LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6936LD50, mol/kg
Fish Toxicity1.2678pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5660pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry,EggsJapan0.02ppm
Chicken,EggsJapan0.02ppm
Chicken,KidneyJapan0.03ppm
Chicken,Edible OffalJapan0.03ppm
Chicken,LiverJapan0.03ppm
Chicken,FatJapan0.03ppm
Chicken,MuscleJapan0.03ppm
MilkJapan0.01ppm
Pig,Edible OffalJapan0.01ppm
Cattle,Edible OffalJapan0.01ppm
Pig,KidneyJapan0.01ppm
Cattle,KidneyJapan0.01ppm
Pig,LiverJapan0.01ppm
Cattle,LiverJapan0.01ppm
Pig,FatJapan0.01ppm
Cattle,FatJapan0.01ppm
Pig,MuscleJapan0.01ppm
Cattle,MuscleJapan0.01ppm

References

TitleJournalDatePubmed ID
Effects of Lactobacillus acidophilus dietary supplementation on the performance, intestinal barrier function, rectal microflora and serum immune function in weaned piglets challenged with Escherichia coli lipopolysaccharide.Antonie Van Leeuwenhoek2015 Apr25577203