Milbemectin

Basic Info

Common NameMilbemectin(F06072)
2D Structure
FRCD IDF06072
CAS Number51596-10-2
PubChem CID9828343
FormulaC31H44O7
IUPAC Name

None

InChI Key

ZLBGSRMUSVULIE-GSMJGMFJSA-N

InChI

InChI=1S/C31H44O7/c1-18-7-6-8-23-17-35-28-27(32)21(4)14-26(31(23,28)34)29(33)36-25-15-24(10-9-19(2)13-18)38-30(16-25)12-11-20(3)22(5)37-30/h6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+/t18-,20-,22+,24+,25-,26-,27+,28+,30-,31+/m0/s1

Canonical SMILES

CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)OC1C

Isomeric SMILES

C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)\C)O[C@@H]1C

Synonyms
        
            Milbemycin A3
        
            Milbemectin
        
            51596-10-2
        
            UNII-C76Y8Z9GEX
        
            MILBEMECTIN A3
        
            C76Y8Z9GEX
        
            CHEBI:39228
        
            Matsuguard
        
            Milbeknock
        
            Koromite
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassMacrolides and analogues
SubclassMilbemycins
Intermediate Tree NodesNot available
Direct ParentMilbemycins
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsMilbemycin - Ketal - Oxane - Tetrahydrofuran - Tertiary alcohol - Carboxylic acid ester - Lactone - Secondary alcohol - Acetal - Carboxylic acid derivative - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Alcohol - Organooxygen compound - Organic oxygen compound - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.g. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.

Properties

Property NameProperty Value
Molecular Weight528.686
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count0
Complexity1040
Monoisotopic Mass528.309
Exact Mass528.309
XLogP3.1
Formal Charge0
Heavy Atom Count38
Defined Atom Stereocenter Count10
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+0.6951
Human Intestinal AbsorptionHIA+0.9460
Caco-2 PermeabilityCaco2-0.7328
P-glycoprotein SubstrateSubstrate0.7690
P-glycoprotein InhibitorNon-inhibitor0.6475
Non-inhibitor0.7876
Renal Organic Cation TransporterNon-inhibitor0.7402
Distribution
Subcellular localizationMitochondria0.8427
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8555
CYP450 2D6 SubstrateNon-substrate0.8760
CYP450 3A4 SubstrateSubstrate0.7547
CYP450 1A2 InhibitorNon-inhibitor0.8538
CYP450 2C9 InhibitorNon-inhibitor0.9412
CYP450 2D6 InhibitorNon-inhibitor0.9422
CYP450 2C19 InhibitorNon-inhibitor0.9542
CYP450 3A4 InhibitorNon-inhibitor0.9299
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9126
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9654
Non-inhibitor0.6225
AMES ToxicityNon AMES toxic0.9042
CarcinogensNon-carcinogens0.9720
Fish ToxicityHigh FHMT0.9035
Tetrahymena Pyriformis ToxicityHigh TPT0.9882
Honey Bee ToxicityHigh HBT0.8454
BiodegradationNot ready biodegradable0.9399
Acute Oral ToxicityIII0.6920
Carcinogenicity (Three-class)Non-required0.4624
Model Value Unit
Absorption
Aqueous solubility-4.2924LogS
Caco-2 Permeability0.7889LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5894LD50, mol/kg
Fish Toxicity0.7511pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7907pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.02*06/07/2014
Peaches (Flat peaches/saturn peaches/paraguayas, Nectarines, Other hybrids of Persica vulgaris; syn: Prunus persica, not elsewhere mentioned,)0140030European Union0.02*06/07/2014
Plums (American plums, Beach plums, Cherry plums /myrabolans, Chickasaw plums, Chinese jujubes/red dates/Chinese dates, Damsons/ bullaces, Gages/greengages/Reine Claudes, Japanese plums, Klamath pl...0140040European Union0.02*06/07/2014
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.02*06/07/2014
Papayas (Akee apples, Feijoas/pineapple guavas, Langsats/lanzones/longkongs, Mangosteens, Naranjillas/lulos, Paw paws, Tamarillos,)0163040European Union0.02*06/07/2014
Cherimoyas (Elephant apples, Ilamas, Mammey sapotes, Marmeladedos, Pulasans, Rambutans/hairy litchis, Sapodillas, Sweetsops/sugar apples, Wild sweetsops/custard apples,)0163060European Union0.02*06/07/2014
Brassica vegetables (excluding brassica roots and brassica baby leaf crops)0240000European Union0.02*06/07/2014
Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,)0243010European Union0.02*06/07/2014
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.05*06/07/2014
Laurel/bay leaves (Curry leaves, Kaffir lime leaves, Siamese cassia, Wild betel leaves, Pandan leaves,)0256090European Union0.05*06/07/2014
Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ...0260010European Union0.02*06/07/2014
Borage seeds (Corn gromwell seeds, Evening primrose seeds, Honesty seeds, Honesty seeds, Perilla seeds, Purple viper's bugloss seeds,)0401120European Union0.02*06/07/2014
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.1*06/07/2014
(f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo...1016000European Union0.02*06/07/2014
Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe...0632010European Union0.1*06/07/2014
(d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark...0639000European Union0.1*06/07/2014
Fat1014020European Union0.02*06/07/2014
Muscle1014010European Union0.02*06/07/2014
Tree nuts0120000European Union0.02*06/07/2014
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*06/07/2014