Spinosyn A

Basic Info

Common NameSpinosyn A(F06337)
2D Structure
FRCD IDF06337
CAS Number131929-60-7
PubChem CID443059
FormulaC41H65NO10
IUPAC Name

None

InChI Key

SRJQTHAZUNRMPR-UYQKXTDMSA-N

InChI

InChI=1S/C41H65NO10/c1-10-26-12-11-13-34(52-36-17-16-33(42(5)6)23(3)48-36)22(2)37(44)32-20-30-28(31(32)21-35(43)50-26)15-14-25-18-27(19-29(25)30)51-41-40(47-9)39(46-8)38(45-7)24(4)49-41/h14-15,20,22-31,33-34,36,38-41H,10-13,16-19,21H2,1-9H3/t22-,23-,24+,25-,26+,27-,28-,29-,30-,31+,33+,34+,36+,38+,39-,40-,41+/m1/s1

Canonical SMILES

CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C=CC3C2CC(=O)O1)OC5C(C(C(C(O5)C)OC)OC)OC)C)OC6CCC(C(O6)C)N(C)C

Isomeric SMILES

CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3[C@@H]2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C

Synonyms
        
            A 83543A
        
            Spinosyn A
        
            Lepicidin A
        
            Spinosad factor A
        
            UNII-OY0L59V61N
        
            Spinosyn-A
        
            131929-60-7
        
            CHEBI:9230
        
            OY0L59V61N
        
            (-)-Spinosyn A
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesAminosaccharides
Direct ParentAminoglycosides
Alternative Parents
Molecular FrameworkAliphatic heteropolycyclic compounds
SubstituentsAminoglycoside core - Macrolide - Glycosyl compound - O-glycosyl compound - Monosaccharide - Oxane - Amino acid or derivatives - Carboxylic acid ester - Ketone - Lactone - Tertiary amine - Tertiary aliphatic amine - Monocarboxylic acid or derivatives - Acetal - Ether - Dialkyl ether - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Organic oxide - Amine - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Organic nitrogen compound - Carbonyl group - Aliphatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Properties

Property NameProperty Value
Molecular Weight731.968
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count11
Rotatable Bond Count9
Complexity1290
Monoisotopic Mass731.461
Exact Mass731.461
XLogP4.9
Formal Charge0
Heavy Atom Count52
Defined Atom Stereocenter Count17
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-0.5434
Human Intestinal AbsorptionHIA+0.9662
Caco-2 PermeabilityCaco2+0.5173
P-glycoprotein SubstrateSubstrate0.6897
P-glycoprotein InhibitorInhibitor0.9771
Inhibitor0.8654
Renal Organic Cation TransporterNon-inhibitor0.7038
Distribution
Subcellular localizationMitochondria0.5601
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8568
CYP450 2D6 SubstrateNon-substrate0.8407
CYP450 3A4 SubstrateSubstrate0.7629
CYP450 1A2 InhibitorNon-inhibitor0.7407
CYP450 2C9 InhibitorNon-inhibitor0.8709
CYP450 2D6 InhibitorNon-inhibitor0.8263
CYP450 2C19 InhibitorNon-inhibitor0.8265
CYP450 3A4 InhibitorNon-inhibitor0.5377
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6924
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7689
Non-inhibitor0.8169
AMES ToxicityNon AMES toxic0.6310
CarcinogensNon-carcinogens0.9214
Fish ToxicityHigh FHMT0.9820
Tetrahymena Pyriformis ToxicityHigh TPT0.9397
Honey Bee ToxicityHigh HBT0.6524
BiodegradationNot ready biodegradable0.9669
Acute Oral ToxicityIII0.6423
Carcinogenicity (Three-class)Non-required0.4849
Model Value Unit
Absorption
Aqueous solubility-3.4264LogS
Caco-2 Permeability0.6878LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6850LD50, mol/kg
Fish Toxicity0.5763pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5518pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Citrus fruits0110000European Union0.307/12/2015
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.307/12/2015
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.307/12/2015
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.307/12/2015
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.307/12/2015
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.307/12/2015
Others (2)0110990European Union0.307/12/2015
Tree nuts0120000European Union0.0707/12/2015
Brazil nuts0120020European Union0.0707/12/2015
Cashew nuts0120030European Union0.0707/12/2015
Chestnuts0120040European Union0.0707/12/2015
Coconuts (Areca nuts/betel nuts,)0120050European Union0.0707/12/2015
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.0707/12/2015
Macadamias0120070European Union0.0707/12/2015
Pecans (Hickory nuts,)0120080European Union0.0707/12/2015
Pistachios0120100European Union0.0707/12/2015
Walnuts0120110European Union0.0707/12/2015
Others (2)0120990European Union0.0707/12/2015
Pome fruits0130000European Union0.307/12/2015
Apples (Crab apples/wild apples, Tejocotes,)0130010European Union0.307/12/2015

References

TitleJournalDatePubmed ID
Spinosad interacts synergistically with the insect pathogen Metarhizium anisopliae against the exotic wireworms Agriotes lineatus and Agriotes obscurus (Coleoptera: Elateridae).J Econ Entomol2007 Feb17370806