NP-MRD: Showing NP-Card for 5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid (NP0059608)

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Record Information

Version

2.0

Created at

2022-04-28 04:50:07 UTC

Updated at

2022-04-28 04:50:07 UTC

NP-MRD ID

NP0059608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid

Description

(1R,2S,4R,5R,6S,7S,9S,12R)-4,7-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-5-yl (2R,3S)-3-phenyloxirane-2-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). 5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid is found in Rzedowskia tolantonguensis. Based on a literature review very few articles have been published on (1R,2S,4R,5R,6S,7S,9S,12R)-4,7-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁶]Dodecan-5-yl (2R,3S)-3-phenyloxirane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206502D          

 38 42  0  0  1  0            999 V2000
    1.1500    0.6634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  1  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282206502D          

 38 42  0  0  1  0            999 V2000
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    1.8099    0.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2262    1.0376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2164    1.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162    2.1869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3962    2.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5713    2.8884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012    3.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  8 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  6 26  1  1  0  0  0
  6 27  1  6  0  0  0
  5 28  1  1  0  0  0
 28 29  1  0  0  0  0
  1 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  5 32  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  1  1  0  0  0
  4 34  1  6  0  0  0
  3 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059608

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O10/c1-14(29)34-18-13-26(5,33)28-22(31)17(25(3,4)38-28)12-19(35-15(2)30)27(28,6)23(18)37-24(32)21-20(36-21)16-10-8-7-9-11-16/h7-11,17-23,31,33H,12-13H2,1-6H3/t17-,18+,19-,20-,21+,22+,23-,26-,27-,28+/m0/s1

> <INCHI_KEY>
BRKBLUGVYARNGW-CADXXCQMSA-N

> <FORMULA>
C28H36O10

> <MOLECULAR_WEIGHT>
532.586

> <EXACT_MASS>
532.230847359

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.02078656717714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,5R,6S,7S,9S,12R)-4,7-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl (2R,3S)-3-phenyloxirane-2-carboxylate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.1316910946666667

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.02540244954044

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.321898228377698

> <JCHEM_PKA_STRONGEST_BASIC>
-3.378258416631893

> <JCHEM_POLAR_SURFACE_AREA>
141.12

> <JCHEM_REFRACTIVITY>
129.6317

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,6S,7S,9S,12R)-4,7-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl (2R,3S)-3-phenyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.147   1.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.906   2.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.501   2.741   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.277   1.317   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.508  -0.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.522  -1.366   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.074  -1.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.714   0.187   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.829   1.454   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.479   2.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.014   2.984   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.897   1.722   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.664   4.380   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.530   5.914   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.926   5.263   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.460   5.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.111   6.793   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.645   6.927   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.528   5.665   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.878   4.270   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.343   4.136   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.247   0.329   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.136  -0.929   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.670  -0.788   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.492  -2.328   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.655  -2.900   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.342  -2.355   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.187  -1.176   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.788  -0.337   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.850  -1.559   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.257  -0.169   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.378   0.607   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.156   1.937   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.004   2.674   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.257   4.082   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.473   5.408   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.933   5.392   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.229   6.749   0.000  0.00  0.00           C+0
CONECT    1    2   29   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5    9   34                                             
CONECT    5    4    6   28   32                                             
CONECT    6    5    7   26   27                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    8   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    5   29                                                       
CONECT   29   28    1   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    5    1   33                                                  
CONECT   33   32                                                            
CONECT   34    4                                                            
CONECT   35    3   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4R,5R,6S,7S,9S,12R)-4,7-Bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0,]dodecan-5-yl (2R,3S)-3-phenyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₆O₁₀

Average Mass

532.5860 Da

Monoisotopic Mass

532.23085 Da

IUPAC Name

(1R,2S,4R,5R,6S,7S,9S,12R)-4,7-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl (2R,3S)-3-phenyloxirane-2-carboxylate

Traditional Name

(1R,2S,4R,5R,6S,7S,9S,12R)-4,7-bis(acetyloxy)-2,12-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-5-yl (2R,3S)-3-phenyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H36O10/c1-14(29)34-18-13-26(5,33)28-22(31)17(25(3,4)38-28)12-19(35-15(2)30)27(28,6)23(18)37-24(32)21-20(36-21)16-10-8-7-9-11-16/h7-11,17-23,31,33H,12-13H2,1-6H3/t17-,18+,19-,20-,21+,22+,23-,26-,27-,28+/m0/s1

InChI Key

BRKBLUGVYARNGW-CADXXCQMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Rzedowskia tolantonguensis	Plant	KNApSAcK

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
Tricarboxylic acid or derivatives
Oxepane
Benzenoid
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Monocyclic benzene moiety
Cyclitol or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.22	ALOGPS
logP	1.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.32	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	141.12 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.63 m³·mol⁻¹	ChemAxon
Polarizability	54.02 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

163041146

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid (NP0059608)

MOL for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

3D MOL for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

3D SDF for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

3D-SDF for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

PDB for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

3D PDB for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

SMILES for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

INCHI for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

Structure for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)

3D Structure for NP0059608 (5,7-bis(Acetyloxy)octahydro-9,10-dihydroxy-2,2,5a,9-tetramethyl-2H-3,9a-methano-1-benzoxepin-6-yl ester 3-phenyloxiranecarboxylic acid)