Efrotomycin

Basic Info

Common NameEfrotomycin(F06128)
2D Structure
FRCD IDF06128
CAS Number56592-32-6
PubChem CID54676086
FormulaC59H88N2O20
IUPAC Name

2-[2,3-dihydroxy-4-[3-hydroxy-5-(4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl)oxy-4-methoxy-6-methyloxan-2-yl]oxy-5,5-dimethyl-6-[(1E,3E)-penta-1,3-dienyl]oxan-2-yl]-N-[(2E,4E)-7-[3,4-dihydroxy-5-[(1E,3E,5E,7E)-7-hydroxy-6-methyl-7-(1-methyl-2,4-dioxopyridin-3-ylidene)hepta-1,3,5-trienyl]oxolan-2-yl]-6-methoxy-5-methylocta-2,4-dienyl]butanamide

InChI Key

ZLECMEJICSWJLT-LIWMBINXSA-N

InChI

InChI=1S/C59H88N2O20/c1-15-17-19-27-39-58(8,9)53(80-56-45(67)50(74-13)49(35(7)76-56)79-57-51(75-14)44(66)48(73-12)34(6)77-57)52(68)59(71,81-39)36(16-2)54(69)60-29-23-22-25-32(4)46(72-11)33(5)47-43(65)42(64)38(78-47)26-21-18-20-24-31(3)41(63)40-37(62)28-30-61(10)55(40)70/h15,17-28,30,33-36,38-39,42-53,56-57,63-68,71H,16,29H2,1-14H3,(H,60,69)/b17-15+,20-18+,23-22+,26-21+,27-19+,31-24+,32-25+,41-40+

Canonical SMILES

CCC(C(=O)NCC=CC=C(C)C(C(C)C1C(C(C(O1)C=CC=CC=C(C)C(=C2C(=O)C=CN(C2=O)C)O)O)O)OC)C3(C(C(C(C(O3)C=CC=CC)(C)C)OC4C(C(C(C(O4)C)OC5C(C(C(C(O5)C)OC)O)OC)OC)O)O)O

Isomeric SMILES

CCC(C(=O)NC/C=C/C=C(\C)/C(C(C)C1C(C(C(O1)/C=C/C=C/C=C(\C)/C(=C\2/C(=O)C=CN(C2=O)C)/O)O)O)OC)C3(C(C(C(C(O3)/C=C/C=C/C)(C)C)OC4C(C(C(C(O4)C)OC5C(C(C(C(O5)C)OC)O)OC)OC)O)O)O

Synonyms
        
            Efrotomycin [USAN:BAN:INN]
        
            Efrotomycin
        
            Producil
        
            Antibiotic FR 02A
        
            Efrotomycine [French]
        
            Efrotomicina [Spanish]
        
            FR 02A
        
            MK-621
        
            56592-32-6
        
            BRN 5230192
Classifies
                

                  
                    Predicted: Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesGlycosyl compounds
Direct ParentO-glycosyl compounds
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsC-glycosyl compound - Disaccharide - O-glycosyl compound - Tetrahydropyridine - Hydropyridine - Oxane - Vinylogous amide - Vinylogous acid - Tertiary carboxylic acid amide - Oxolane - Carboxamide group - Hemiacetal - Ketone - Lactam - Cyclic ketone - Secondary alcohol - Acetal - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Dialkyl ether - Enol - Ether - Oxacycle - Azacycle - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Carbonyl group - Alcohol - Hydrocarbon derivative - Aldehyde - Organopnictogen compound - Organic nitrogen compound - Organonitrogen compound - Organic oxide - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Properties

Property NameProperty Value
Molecular Weight1145.347
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count20
Rotatable Bond Count23
Complexity2410
Monoisotopic Mass1144.593
Exact Mass1144.593
XLogP3.7
Formal Charge0
Heavy Atom Count81
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count21
Defined Bond Stereocenter Count8
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9796
Human Intestinal AbsorptionHIA-0.5831
Caco-2 PermeabilityCaco2-0.6766
P-glycoprotein SubstrateSubstrate0.7548
P-glycoprotein InhibitorInhibitor0.7553
Non-inhibitor0.8132
Renal Organic Cation TransporterNon-inhibitor0.9020
Distribution
Subcellular localizationMitochondria0.6208
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8546
CYP450 2D6 SubstrateNon-substrate0.8487
CYP450 3A4 SubstrateSubstrate0.6405
CYP450 1A2 InhibitorNon-inhibitor0.8214
CYP450 2C9 InhibitorNon-inhibitor0.7953
CYP450 2D6 InhibitorNon-inhibitor0.8807
CYP450 2C19 InhibitorNon-inhibitor0.7930
CYP450 3A4 InhibitorNon-inhibitor0.8846
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7809
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9929
Non-inhibitor0.7556
AMES ToxicityNon AMES toxic0.6320
CarcinogensNon-carcinogens0.9139
Fish ToxicityHigh FHMT0.8470
Tetrahymena Pyriformis ToxicityHigh TPT0.9443
Honey Bee ToxicityHigh HBT0.5081
BiodegradationNot ready biodegradable0.9704
Acute Oral ToxicityIII0.5957
Carcinogenicity (Three-class)Non-required0.5345
Model Value Unit
Absorption
Aqueous solubility-2.2897LogS
Caco-2 Permeability0.1523LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.7581LD50, mol/kg
Fish Toxicity1.2430pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3918pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pig,Edible OffalJapan0.03ppm
Pig,KidneyJapan0.03ppm
Pig,LiverJapan0.03ppm
Pig,FatJapan0.03ppm
Pig,MuscleJapan0.03ppm