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Record Information
Version1.0
Created at2022-09-12 15:58:54 UTC
Updated at2022-09-12 15:58:55 UTC
NP-MRD IDNP0330535
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one
DescriptionEpianastrephin belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one is found in Anastrepha ludens and Anastrepha suspensa. It was first documented in 1988 (PMID: 24276529). Based on a literature review a significant number of articles have been published on epianastrephin (PMID: 11673844) (PMID: 11667494) (PMID: 24248794) (PMID: 24249180) (PMID: 24254911).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC12H18O2
Average Mass194.2740 Da
Monoisotopic Mass194.13068 Da
IUPAC Name(3aS,4S,7aS)-4-ethenyl-4,7a-dimethyl-octahydro-1-benzofuran-2-one
Traditional Name(3aS,4S,7aS)-4-ethenyl-4,7a-dimethyl-tetrahydro-3H-1-benzofuran-2-one
CAS Registry NumberNot Available
SMILES
C[C@]12CCC[C@@](C)(C=C)[C@@H]1CC(=O)O2
InChI Identifier
InChI=1S/C12H18O2/c1-4-11(2)6-5-7-12(3)9(11)8-10(13)14-12/h4,9H,1,5-8H2,2-3H3/t9-,11+,12-/m0/s1
InChI KeyVWOPTUCATATVGQ-WCQGTBRESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anastrepha ludensLOTUS Database
Anastrepha suspensaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Gamma butyrolactone
  • Oxolane
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.44ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity54.83 m³·mol⁻¹ChemAxon
Polarizability21.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9031654
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10856363
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lu F, Teal PE: Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Arch Insect Biochem Physiol. 2001 Nov;48(3):144-54. doi: 10.1002/arch.1067. [PubMed:11673844 ]
  2. Battiste MA, Wydra RL, Strekowski L: Efficient and Stereoselective Synthesis of 10-Hydroxy-4,8-dimethyldeca-3(E),8(E)-dienoic Acid, a Precursor to (3E,8E)-Suspensolide, Anastrephin, and Epianastrephin. J Org Chem. 1996 Sep 6;61(18):6454-6455. doi: 10.1021/jo960870s. [PubMed:11667494 ]
  3. Ponce WP, Nation JL, Emmel TC, Smittle BJ, Teal PE: Quantitative analysis of pheromone production in irradiated Caribbean fruit fly males,Anastrepha suspensa (Loew). J Chem Ecol. 1993 Dec;19(12):3045-56. doi: 10.1007/BF00980601. [PubMed:24248794 ]
  4. Baker JD, Heath RR: NMR spectral assignment of lactone pheromone components emitted by Caribbean and Mexican fruit flies. J Chem Ecol. 1993 Jul;19(7):1511-9. doi: 10.1007/BF00984894. [PubMed:24249180 ]
  5. Rocca JR, Nation JL, Strekowski L, Battiste MA: Comparison of volatiles emitted by male caribbean and mexican fruit flies. J Chem Ecol. 1992 Feb;18(2):223-44. doi: 10.1007/BF00993755. [PubMed:24254911 ]
  6. Robacker DC: Behavioral responses of female Mexican fruit flies,Anastrepha ludens, to components of male-produced sex pheromone. J Chem Ecol. 1988 Sep;14(9):1715-26. doi: 10.1007/BF01014639. [PubMed:24276529 ]
  7. LOTUS database [Link]