NP-MRD: Showing NP-Card for (3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one (NP0330535)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 15:58:54 UTC

Updated at

2022-09-12 15:58:55 UTC

NP-MRD ID

NP0330535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one

Description

Epianastrephin 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. (3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one 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

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    3.2148    0.3017    0.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    0.9242    0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426    0.1794   -0.2259 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2402   -1.2724   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7067    0.5448   -1.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589   -0.0250   -2.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681    0.1718   -1.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512   -0.0103    0.0907 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7051   -1.3981    0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4160    0.8112    0.9037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488    0.9700    2.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049    1.3362    3.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3089    0.6405    1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2464    0.6584    0.4493 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0707    0.8527    1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2777   -0.7731    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296    2.0078    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4618   -1.6960    0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700   -1.8717   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1803   -1.4315   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429    0.1754   -2.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    1.6632   -1.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691    0.4454   -3.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767   -1.1108   -2.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2559    1.1502   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208   -0.5984   -1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959   -1.7835    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -2.1342   -0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6446   -1.5296    1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    1.3936    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464   -0.3376    2.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3952    1.7457    0.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  1
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  1
  2  1  2  3
  3 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 14  8  1  0
 10  8  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  7 25  1  0
  7 26  1  0
  6 23  1  0
  6 24  1  0
  5 21  1  0
  5 22  1  0
  4 18  1  0
  4 19  1  0
  4 20  1  0
  2 17  1  0
  1 15  1  0
  1 16  1  0
 14 32  1  6
 13 30  1  0
 13 31  1  0
M  END


  Mrv1652309122217582D          

 14 15  0  0  1  0            999 V2000
    4.6217    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
  3 14  1  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330535

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
VWOPTUCATATVGQ-WCQGTBRESA-N

> <FORMULA>
C12H18O2

> <MOLECULAR_WEIGHT>
194.274

> <EXACT_MASS>
194.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.77991199222391

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,4S,7aS)-4-ethenyl-4,7a-dimethyl-octahydro-1-benzofuran-2-one

> <JCHEM_LOGP>
2.4426878773333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0549428106954375

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
54.8283

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,7aS)-4-ethenyl-4,7a-dimethyl-tetrahydro-3H-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       8.627   3.222   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.111   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.131   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.626  -1.532   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   14                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    3    8                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₈O₂

Average Mass

194.2740 Da

Monoisotopic Mass

194.13068 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 Number

Not 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 Key

VWOPTUCATATVGQ-WCQGTBRESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anastrepha ludens	LOTUS Database	35616633
Anastrepha suspensa	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.44	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	54.83 m³·mol⁻¹	ChemAxon
Polarizability	21.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9031654

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10856363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
LOTUS database [Link]

Showing NP-Card for (3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one (NP0330535)

MOL for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

3D MOL for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

3D SDF for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

3D-SDF for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

PDB for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

3D PDB for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

SMILES for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

INCHI for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

Structure for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)

3D Structure for NP0330535 ((3as,4s,7as)-4-ethenyl-4,7a-dimethyl-tetrahydro-3h-1-benzofuran-2-one)