NP-MRD: Showing NP-Card for methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate (NP0158067)

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Record Information

Version

2.0

Created at

2022-09-02 15:35:42 UTC

Updated at

2022-09-02 15:35:43 UTC

NP-MRD ID

NP0158067

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate

Description

Methyl 2-[(1R)-2-[(R,1bS,3R,4R,5aS,5bS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate is found in Toona ciliata. Based on a literature review very few articles have been published on methyl 2-[(1R)-2-[(R,1bS,3R,4R,5aS,5bS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217352D          

 35 39  0  0  1  0            999 V2000
    1.5231    2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147    1.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8343    1.6432    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1623    2.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819    2.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099    3.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184    3.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464    4.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988    3.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
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  9 10  1  0  0  0  0
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  3 18  1  0  0  0  0
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 27 31  2  0  0  0  0
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 33 34  1  6  0  0  0
 35 34  1  1  0  0  0
  2 35  1  0  0  0  0
 33 35  1  0  0  0  0
 24 35  1  0  0  0  0
M  END

     RDKit          2D

 69 73  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309022217352D          

 35 39  0  0  1  0            999 V2000
    1.5231    2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 34  1  1  0  0  0
  2 35  1  0  0  0  0
 33 35  1  0  0  0  0
 24 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158067

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1C(C=CC(=O)C1(C)C)[C@H]1[C@@H](C[C@@]2(C)[C@@H](C[C@@H]3O[C@@]23C1=C)C1=COC=C1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O7/c1-15-25(18-7-8-22(30)26(3,4)20(18)12-24(31)32-6)21(34-16(2)29)13-27(5)19(17-9-10-33-14-17)11-23-28(15,27)35-23/h7-10,14,18-21,23,25H,1,11-13H2,2-6H3/t18?,19-,20+,21+,23-,25-,27-,28+/m0/s1

> <INCHI_KEY>
GQARDYJAWJOMJY-BCOREWIWSA-N

> <FORMULA>
C28H34O7

> <MOLECULAR_WEIGHT>
482.573

> <EXACT_MASS>
482.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R)-2-[(R,1bS,3R,4R,5aS,5bS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.6019835603333323

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.876345668887293

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7858878514607843

> <JCHEM_POLAR_SURFACE_AREA>
95.34000000000002

> <JCHEM_REFRACTIVITY>
127.52299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R)-2-[(R,1bS,3R,4R,5aS,5bS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-hexahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.843   4.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.761   2.891   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.291   3.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.903   4.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.433   4.656   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.045   6.070   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.128   7.306   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.740   8.719   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.598   7.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.690   8.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.100   7.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.985   5.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.456   5.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.538   6.778   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.150   8.191   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.008   6.602   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.091   7.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.208   1.830   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.738   2.007   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.656   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.185   0.946   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.043  -0.643   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.596   0.417   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.066   0.241   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.849  -1.085   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.173  -1.014   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.664  -2.473   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.133  -2.935   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.148  -4.475   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.688  -4.965   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.771  -3.728   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.704  -0.552   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.689   0.988   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.994   2.497   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.148   1.478   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18    3   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   26   35                                             
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27                                                       
CONECT   32   26   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33   35                                                       
CONECT   35   34    2   33   24                                             
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1R)-2-[(R,1BS,3R,4R,5as,5BS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₇

Average Mass

482.5730 Da

Monoisotopic Mass

482.23045 Da

IUPAC Name

methyl 2-[(1R)-2-[(R,1bS,3R,4R,5aS,5bS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate

Traditional Name

methyl [(1R)-2-[(R,1bS,3R,4R,5aS,5bS)-3-(acetyloxy)--(furan-3-yl)-1b-methyl-5-methylidene-hexahydroindeno[1,7a-b]oxiren-4-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1C(C=CC(=O)C1(C)C)[C@H]1[C@@H](C[C@@]2(C)[C@@H](C[C@@H]3O[C@@]23C1=C)C1=COC=C1)OC(C)=O

InChI Identifier

InChI=1S/C28H34O7/c1-15-25(18-7-8-22(30)26(3,4)20(18)12-24(31)32-6)21(34-16(2)29)13-27(5)19(17-9-10-33-14-17)11-23-28(15,27)35-23/h7-10,14,18-21,23,25H,1,11-13H2,2-6H3/t18?,19-,20+,21+,23-,25-,27-,28+/m0/s1

InChI Key

GQARDYJAWJOMJY-BCOREWIWSA-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
Toona ciliata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Oxane
Dicarboxylic acid or derivatives
Heteroaromatic compound
Methyl ester
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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
logP	4.15	ALOGPS
logP	3.6	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	16.88	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.34 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.52 m³·mol⁻¹	ChemAxon
Polarizability	0 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

163014901

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-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate (NP0158067)

MOL for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D MOL for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D SDF for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D-SDF for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

PDB for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D PDB for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

SMILES for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

INCHI for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

Structure for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D Structure for NP0158067 (methyl 2-[(1r)-2-[(1as,3s,3as,5r,6r,7as)-5-(acetyloxy)-3-(furan-3-yl)-3a-methyl-7-methylidene-hexahydroindeno[1,7a-b]oxiren-6-yl]-6,6-dimethyl-5-oxocyclohex-3-en-1-yl]acetate)