Doramectin

Basic Info

Common NameDoramectin(F05738)
2D Structure
FRCD IDF05738
CAS Number117704-25-3
PubChem CID9832750
FormulaC50H74O14
IUPAC Name

None

InChI Key

QLFZZSKTJWDQOS-YDBLARSUSA-N

InChI

InChI=1S/C50H74O14/c1-27-13-12-16-34-26-57-47-42(51)30(4)21-37(50(34,47)54)48(53)60-36-22-35(63-49(25-36)20-19-29(3)45(64-49)33-14-10-9-11-15-33)18-17-28(2)44(27)61-41-24-39(56-8)46(32(6)59-41)62-40-23-38(55-7)43(52)31(5)58-40/h12-13,16-17,19-21,27,29,31-33,35-47,51-52,54H,9-11,14-15,18,22-26H2,1-8H3/b13-12+,28-17+,34-16+/t27-,29-,31-,32-,35+,36-,37-,38-,39-,40-,41-,42+,43-,44-,45-,46-,47+,49+,50+/m0/s1

Canonical SMILES

CC1C=CC=C2COC3C2(C(C=C(C3O)C)C(=O)OC4CC(CC=C(C1OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)O)OC)OC)C)OC7(C4)C=CC(C(O7)C8CCCCC8)C)O

Isomeric SMILES

C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(/[C@H]1O[C@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O)OC)OC)\C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C8CCCCC8)C)O

Synonyms
        
            Doramectin
        
            117704-25-3
        
            UNII-KGD7A54H5P
        
            KGD7A54H5P
        
            Doramectine [INN-French]
        
            Doramectinum [INN-Latin]
        
            Doramectina [INN-Spanish]
        
            Doramectin [USAN:INN:BAN]
        
            HSDB 7452
        
            Doramectina
Classifies
                

                  
                    Pesticide
                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassMacrolides and analogues
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentMacrolides and analogues
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsMacrolide - Disaccharide - Glycosyl compound - O-glycosyl compound - Ketal - Oxane - Pyran - Tetrahydrofuran - Tertiary alcohol - Secondary alcohol - Carboxylic acid ester - Lactone - Acetal - Carboxylic acid derivative - Organoheterocyclic compound - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organic oxygen compound - Alcohol - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Properties

Property NameProperty Value
Molecular Weight899.128
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Complexity1790
Monoisotopic Mass898.508
Exact Mass898.508
XLogP4.5
Formal Charge0
Heavy Atom Count64
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.7271
Human Intestinal AbsorptionHIA+0.9300
Caco-2 PermeabilityCaco2-0.7425
P-glycoprotein SubstrateSubstrate0.7773
P-glycoprotein InhibitorInhibitor0.5632
Inhibitor0.7586
Renal Organic Cation TransporterNon-inhibitor0.7302
Distribution
Subcellular localizationMitochondria0.8665
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8621
CYP450 2D6 SubstrateNon-substrate0.8837
CYP450 3A4 SubstrateSubstrate0.7595
CYP450 1A2 InhibitorNon-inhibitor0.8955
CYP450 2C9 InhibitorNon-inhibitor0.9181
CYP450 2D6 InhibitorNon-inhibitor0.9301
CYP450 2C19 InhibitorNon-inhibitor0.9303
CYP450 3A4 InhibitorNon-inhibitor0.9431
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8093
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9773
Inhibitor0.5670
AMES ToxicityNon AMES toxic0.8648
CarcinogensNon-carcinogens0.9674
Fish ToxicityHigh FHMT0.9101
Tetrahymena Pyriformis ToxicityHigh TPT0.9882
Honey Bee ToxicityHigh HBT0.8555
BiodegradationNot ready biodegradable0.9747
Acute Oral ToxicityI0.5855
Carcinogenicity (Three-class)Non-required0.5267
Model Value Unit
Absorption
Aqueous solubility-3.9688LogS
Caco-2 Permeability0.5845LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity4.1425LD50, mol/kg
Fish Toxicity0.6291pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8440pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Poultry,EggsJapan0.005ppm
Chicken,Edible OffalJapan0.005ppm
Other Poultry Animals,KidneyJapan0.005ppm
Chicken,KidneyJapan0.005ppm
Other Poultry Animals,LiverJapan0.005ppm
Chicken,LiverJapan0.005ppm
Other Poultry Animals,FatJapan0.005ppm
Chicken,FatJapan0.005ppm
Other Poultry Animals,MuscleJapan0.005ppm
Chicken,MuscleJapan0.005ppm
MilkJapan0.03ppm
Other Terrestrial Mammals,Edible OffalJapan0.05ppm
Pig,Edible OffalJapan0.03ppm
Cattle,Edible OffalJapan0.03ppm
Other Terrestrial Mammals,KidneyJapan0.04ppm
Pig,KidneyJapan0.03ppm
Cattle,KidneyJapan0.03ppm
Other Terrestrial Mammals,LiverJapan0.05ppm
Pig,LiverJapan0.1ppm
Cattle,LiverJapan0.1ppm

References

TitleJournalDatePubmed ID
Multiresidue method for simultaneous analysis of aflatoxin M1, avermectins, organophosphate pesticides and milbemycin in milk by ultra-performance liquid chromatography coupled to tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2016 Jun27144891
P-gp substrate-induced neurotoxicity in an Abcb1a knock-in/Abcb1b knock-out mouse model with a mutated canine ABCB1 targeted insertion.Res Vet Sci2013 Jun23186803
Endectocide use in cattle and fecal residues: environmental effects in Canada.Can J Vet Res2006 Jan16548326