NP-MRD: Showing NP-Card for methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate (NP0234767)

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Record Information

Version

2.0

Created at

2022-09-06 17:00:40 UTC

Updated at

2022-09-06 17:00:40 UTC

NP-MRD ID

NP0234767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate

Description

Methyl 2-[(3R,4R)-4-[(1S,4aR,6S,8aR)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-3-yl]acetate belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate is found in Harrisonia abyssinica. Based on a literature review very few articles have been published on methyl 2-[(3R,4R)-4-[(1S,4aR,6S,8aR)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-3-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062219002D          

 34 37  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0617   -2.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5431   -3.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589   -2.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236   -3.5925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714   -2.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -1.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2858   -1.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2037    0.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0807    0.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1904    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5253    1.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  9 10  1  0  0  0  0
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 17 18  1  0  0  0  0
  3 19  1  0  0  0  0
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 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062219002D          

 34 37  0  0  1  0            999 V2000
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    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0234767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1[C@H](C=CC(=O)OC1(C)C)[C@@H]1CC[C@]2(C)[C@H](OC(=O)C[C@@]2(O)C1=C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-15-17(18-6-7-20(27)34-24(2,3)19(18)12-21(28)31-5)8-10-25(4)23(16-9-11-32-14-16)33-22(29)13-26(15,25)30/h6-7,9,11,14,17-19,23,30H,1,8,10,12-13H2,2-5H3/t17-,18-,19-,23-,25-,26-/m1/s1

> <INCHI_KEY>
ZLNOGXIGLHZEFW-VAPJYHBQSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.534

> <EXACT_MASS>
472.20971799

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.53772269937648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(3R,4R)-4-[(1S,4aR,6S,8aR)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-3-yl]acetate

> <JCHEM_LOGP>
2.889264212666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.09057123951602

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.482393278257273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8887502519258246

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000002

> <JCHEM_REFRACTIVITY>
121.33009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(3R,4R)-4-[(1S,4aR,6S,8aR)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1H-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.115  -4.616   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.014  -5.663   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.537  -5.434   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.404  -6.706   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.307  -4.100   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.744  -2.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.267  -2.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.859  -1.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.272  -2.212   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.043  -0.690   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.247   0.270   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.680  -0.292   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.017   1.793   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.221   2.753   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.565   3.910   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.105   3.910   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.581   2.445   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    4   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   33                                             
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   23   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32    2   21   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(3R,4R)-4-[(1S,4ar,6S,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-octahydro-1H-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-3-yl]acetic acid	Generator

Chemical Formula

C₂₆H₃₂O₈

Average Mass

472.5340 Da

Monoisotopic Mass

472.20972 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1[C@H](C=CC(=O)OC1(C)C)[C@@H]1CC[C@]2(C)[C@H](OC(=O)C[C@@]2(O)C1=C)C1=COC=C1

InChI Identifier

InChI=1S/C26H32O8/c1-15-17(18-6-7-20(27)34-24(2,3)19(18)12-21(28)31-5)8-10-25(4)23(16-9-11-32-14-16)33-22(29)13-26(15,25)30/h6-7,9,11,14,17-19,23,30H,1,8,10,12-13H2,2-5H3/t17-,18-,19-,23-,25-,26-/m1/s1

InChI Key

ZLNOGXIGLHZEFW-VAPJYHBQSA-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
Harrisonia abyssinica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162889371

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate (NP0234767)

MOL for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

3D MOL for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

3D SDF for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

3D-SDF for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

PDB for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

3D PDB for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

SMILES for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

INCHI for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

Structure for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)

3D Structure for NP0234767 (methyl 2-[(3r,4r)-4-[(1r,4ar,6s,8ar)-1-(furan-3-yl)-4a-hydroxy-8a-methyl-5-methylidene-3-oxo-tetrahydro-1h-2-benzopyran-6-yl]-2,2-dimethyl-7-oxo-3,4-dihydrooxepin-3-yl]acetate)