Carbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester (CHEM010850)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:29:07 UTC
Update Date2016-11-09 01:14:16 UTC
Accession NumberCHEM010850
Identification
Common NameCarbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl ester
ClassSmall Molecule
DescriptionAn azaspiro compound that is methoxycyclohexane which is fused at position 4 to the 5-position of a 1,5-dihydro-2H-pyrrol-2-one that is substituted at positions 3 and 4 by 2,5-dimethylphenyl and (ethoxycarbonyl)oxy groups, respectively (the cis isomer). It is a proinsecticide (via hydrolysis of the ethyl carbonate group to give the corresponding 4-hydroxypyrrol-2-one, "spirotetramat-enol") and is used for the control of a wide range of sucking insects on fruit and potato crops.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
cis-3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonateChEBI
cis-3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethylcarbonateChEBI
Ethyl cis-8-methoxy-2-oxo-3-(2,5-xylyl)-1-azaspiro[4.5]dec-3-en-4-yl carbonateChEBI
MoventoChEBI
UltorChEBI
cis-3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonic acidGenerator
cis-3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethylcarbonic acidGenerator
Ethyl cis-8-methoxy-2-oxo-3-(2,5-xylyl)-1-azaspiro[4.5]dec-3-en-4-yl carbonic acidGenerator
Chemical FormulaC21H27NO5
Average Molecular Mass373.449 g/mol
Monoisotopic Mass373.189 g/mol
CAS Registry Number203313-25-1
IUPAC Nameethyl (5s,8s)-3-(2,5-dimethylphenyl)-2-hydroxy-8-methoxy-1-azaspiro[4.5]deca-1,3-dien-4-yl carbonate
Traditional Nameethyl (5s,8s)-3-(2,5-dimethylphenyl)-2-hydroxy-8-methoxy-1-azaspiro[4.5]deca-1,3-dien-4-yl carbonate
SMILES[H][C@@]1(CC[C@]2(CC1)N=C(O)C(=C2OC(=O)OCC)C1=C(C)C=CC(C)=C1)OC
InChI IdentifierInChI=1S/C21H27NO5/c1-5-26-20(24)27-18-17(16-12-13(2)6-7-14(16)3)19(23)22-21(18)10-8-15(25-4)9-11-21/h6-7,12,15H,5,8-11H2,1-4H3,(H,22,23)/t15-,21+
InChI KeyCLSVJBIHYWPGQY-GGYDESQDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-xylenes. These are aromatic compounds that contain a p-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 4-positions.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct Parentp-Xylenes
Alternative Parents
Substituents
  • P-xylene
  • Carbonic acid diester
  • Enol ester
  • Pyrroline
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Lactam
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Dialkyl ether
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.008 g/LALOGPS
logP3.63ALOGPS
logP4.28ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)5.28ChemAxon
pKa (Strongest Basic)1.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.35 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.99 m³·mol⁻¹ChemAxon
Polarizability41.49 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-0179000000-0e94ebd8c36c36aabad1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1293000000-84db4a3480ff29ad11d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1970000000-1a6e5ef878f4be395a57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1019000000-ce95467f9ccd2d303b4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fs-6059000000-f0e4a4fdc8bc2ea1ca0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056u-2940000000-e324fc6f3c2d116af12aSpectrum
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 IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSpirotetramat
Chemspider IDNot Available
ChEBI ID81975
PubChem Compound IDNot Available
Kegg Compound IDC18807
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22160136
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22531003
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22872376
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24772560
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24835551
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25281882
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26081578
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26304426
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26383737
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26449612
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26743711
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26898726
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27083908
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27788413
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27857899
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27917277
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27989834
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=28139069
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28334236