NP-MRD: Showing NP-Card for 4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate (NP0292015)

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Record Information

Version

2.0

Created at

2022-09-09 23:20:30 UTC

Updated at

2022-09-09 23:20:31 UTC

NP-MRD ID

NP0292015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate

Description

4,5-Bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-12-yl furan-3-carboxylate belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). 4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate is found in Celastrus orbiculatus. 4,5-Bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-12-yl furan-3-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161505282D          

 41 45  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161505282D          

 41 45  0  0  0  0            999 V2000
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    0.6205   -2.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154    0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    1.4538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575    1.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    1.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0816    0.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830   -1.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0454   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2047   -2.7071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5343   -3.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3558   -3.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8330   -3.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889   -4.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675   -4.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -3.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 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
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 27  1  0  0  0  0
 19 28  1  0  0  0  0
  2 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292015

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC(OC(C)=O)C(OC(C)=O)C2(C)C(CC3C(OC(=O)C4=COC=C4)C12OC3(C)C)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H36O10/c1-17-14-23(37-18(2)32)26(38-19(3)33)30(6)24(39-27(34)20-10-8-7-9-11-20)15-22-25(31(17,30)41-29(22,4)5)40-28(35)21-12-13-36-16-21/h7-13,16-17,22-26H,14-15H2,1-6H3

> <INCHI_KEY>
GAOKKLOHOKIMQT-UHFFFAOYSA-N

> <FORMULA>
C31H36O10

> <MOLECULAR_WEIGHT>
568.619

> <EXACT_MASS>
568.230847359

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.42897038449892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
4.402954683666668

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.051286613229941

> <JCHEM_POLAR_SURFACE_AREA>
127.57000000000002

> <JCHEM_REFRACTIVITY>
142.64059999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       5.418   4.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.523   2.905   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.074   2.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.715   1.354   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.247   2.024   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.621   2.929   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.559   4.513   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.206   2.646   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.830   0.086   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.393  -0.838   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.928  -1.607   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.508  -1.552   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.441  -3.171   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.279   0.223   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.542  -0.964   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.502  -1.201   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.907  -1.128   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.148   0.303   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.379   0.935   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.990  -0.418   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.446  -2.004   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.909  -3.493   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.803  -2.465   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.672  -1.420   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.671  -2.172   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.371  -3.682   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.158  -3.863   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.509   1.678   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.188   2.714   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.787   1.878   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.035   3.349   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.152   1.827   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.822  -2.956   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.818  -4.535   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.249  -5.053   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.731  -5.812   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.264  -5.668   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.155  -6.924   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.513  -8.324   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.979  -8.467   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.088  -7.211   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16   28                                             
CONECT   15   14                                                            
CONECT   16   14   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23                                                       
CONECT   28   19    2   14   29                                             
CONECT   29   28   30                                                       
CONECT   30   29   18   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   16   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
4,5-Bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0,]dodecan-12-yl furan-3-carboxylic acid	Generator
4,5-Bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylic acid	Generator

Chemical Formula

C₃₁H₃₆O₁₀

Average Mass

568.6190 Da

Monoisotopic Mass

568.23085 Da

IUPAC Name

4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate

Traditional Name

4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate

CAS Registry Number

Not Available

SMILES

CC1CC(OC(C)=O)C(OC(C)=O)C2(C)C(CC3C(OC(=O)C4=COC=C4)C12OC3(C)C)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C31H36O10/c1-17-14-23(37-18(2)32)26(38-19(3)33)30(6)24(39-27(34)20-10-8-7-9-11-20)15-22-25(31(17,30)41-29(22,4)5)40-28(35)21-12-13-36-16-21/h7-13,16-17,22-26H,14-15H2,1-6H3

InChI Key

GAOKKLOHOKIMQT-UHFFFAOYSA-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
Celastrus orbiculatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Tetracarboxylic acid or derivatives
Benzoate ester
Furoic acid ester
Benzoic acid or derivatives
Furoic acid or derivatives
Furan-3-carboxylic acid ester
Furan-3-carboxylic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Tetrahydrofuran
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	4.52	ALOGPS
logP	4.4	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	127.57 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	142.64 m³·mol⁻¹	ChemAxon
Polarizability	58.43 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

85142896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate (NP0292015)

MOL for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

3D MOL for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

3D SDF for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

3D-SDF for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

PDB for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

3D PDB for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

SMILES for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

INCHI for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

Structure for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)

3D Structure for NP0292015 (4,5-bis(acetyloxy)-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-12-yl furan-3-carboxylate)