Spinosyn A (CHEM043522)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:00:22 UTC
Update Date2016-11-09 01:22:56 UTC
Accession NumberCHEM043522
Identification
Common NameSpinosyn A
ClassSmall Molecule
DescriptionA spinosyn in which the sugar amino and hydroxy groups are globally methylated. One of the two active ingredients of spinosad.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a 83543aChEBI
Lepicidin aChEBI
Spinosad factor aChEBI
Spinosyn-aMeSH
Chemical FormulaC41H65NO10
Average Molecular Mass731.968 g/mol
Monoisotopic Mass731.461 g/mol
CAS Registry Number131929-60-7
IUPAC Name(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-13-{[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy}-9-ethyl-14-methyl-2-{[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy}-1H,2H,3H,3aH,5aH,5bH,6H,7H,9H,10H,11H,12H,13H,14H,15H,16aH,16bH-as-indaceno[3,2-d]oxacyclododecane-7,15-dione
Traditional Namespinosyn-A
SMILES[H][C@]1(C[C@@]2([H])C=C[C@@]3([H])[C@]4([H])CC(=O)O[C@@]([H])(CC)CCC[C@]([H])(O[C@@]5([H])CC[C@]([H])(N(C)C)[C@@]([H])(C)O5)[C@@]([H])(C)C(=O)C4=C[C@@]3([H])[C@]2([H])C1)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(OC)[C@@]([H])(OC)[C@@]1([H])OC
InChI IdentifierInChI=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
InChI KeySRJQTHAZUNRMPR-UYQKXTDMSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Monosaccharide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP3.98ALOGPS
logP5.6ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)19.45ChemAxon
pKa (Strongest Basic)8.56ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.22 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity197.58 m³·mol⁻¹ChemAxon
Polarizability84.39 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-001i-0000000900-9d942c578735d2857d1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-001i-0300000900-37f4c9e407dbcb106641Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0006-0900000200-4d5f53c686fc5b06a2adSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 50V, positivesplash10-0006-0900000000-10e8387e3763535f5bd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 38V, positivesplash10-0006-1900000100-3cae134ca60981707a9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0102190300-43bec3612d0674f38f96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udu-0504970000-821304e0c5306d85365dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udm-7908640100-002a972467908a292aa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-1301091700-1fa9a9ea926e52c315e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0202191100-12d69fdb81cd1f5cd621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4602590000-fc95ed63cdb165cd40d1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00041878
BiGG IDNot Available
BioCyc IDCPD-13385
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSpinosad
Chemspider IDNot Available
ChEBI ID9230
PubChem Compound ID443059
Kegg Compound IDC11054
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21544146
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21834600
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22097790
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22200799
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22686274
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22885939