NP-MRD: Showing NP-Card for (3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid (NP0270732)

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Record Information

Version

2.0

Created at

2022-09-08 16:46:43 UTC

Updated at

2022-09-08 16:46:44 UTC

NP-MRD ID

NP0270732

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid

Description

Scabronine C belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid is found in Sarcodon scabrosus. Based on a literature review very few articles have been published on Scabronine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309082218462D          

 41 45  0  0  1  0            999 V2000
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  4 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652309082218462D          

 41 45  0  0  1  0            999 V2000
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    6.3960   -2.5551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6047   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -2.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -3.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -2.7442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4749   -3.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075   -3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -3.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5138   -2.6480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0093   -3.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233   -3.1520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2817   -4.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2818   -2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3200   -1.6055    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 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  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 18 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 40 41  1  0  0  0  0
  4 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270732

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2[C@H]3C[C@@H](OC(=O)C4=CC=CC=C4)C(COC(=O)C4=CC=CC=C4)=CC(=O)[C@]3(C)CC[C@]2(CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H36O7/c1-21(2)25-14-15-34(32(38)39)17-16-33(3)26(29(25)34)19-27(41-31(37)23-12-8-5-9-13-23)24(18-28(33)35)20-40-30(36)22-10-6-4-7-11-22/h4-13,18,21,26-27H,14-17,19-20H2,1-3H3,(H,38,39)/t26-,27-,33-,34+/m1/s1

> <INCHI_KEY>
BHACRICJKFFIAH-ABENWPRUSA-N

> <FORMULA>
C34H36O7

> <MOLECULAR_WEIGHT>
556.655

> <EXACT_MASS>
556.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
59.71443951273617

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,5aR,9R,10aR)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-5a-methyl-6-oxo-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]indene-3a-carboxylic acid

> <JCHEM_LOGP>
7.080386494333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.595135508492909

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.00686233743244

> <JCHEM_PKA_STRONGEST_BASIC>
-6.434546894974964

> <JCHEM_POLAR_SURFACE_AREA>
106.97000000000001

> <JCHEM_REFRACTIVITY>
154.5517

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5aR,9R,10aR)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2H,3H,4H,5H,9H,10H,10aH-cyclohepta[e]indene-3a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       0.169   0.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.251  -0.969   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.741  -0.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.844  -2.454   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.806  -3.656   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.343  -3.746   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.988  -2.348   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.484  -1.981   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.802  -0.474   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.656   0.555   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.192   0.077   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.974   2.062   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.828   3.091   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.146   4.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.610   5.075   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.756   4.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.438   2.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.703  -2.921   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.080  -2.230   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.366  -3.077   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.743  -2.386   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.832  -0.848   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.029  -3.232   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.405  -2.541   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.692  -3.388   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.602  -4.925   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.226  -5.616   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.939  -4.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.729  -4.461   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.541  -5.441   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.908  -6.936   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.034  -5.123   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.620  -6.547   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.187  -6.409   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.650  -6.319   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.959  -4.943   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.017  -6.134   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.537  -5.884   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.526  -7.575   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.526  -4.535   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.597  -2.997   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   41                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    8   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   18   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    5   37   40                                             
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   36   41                                                       
CONECT   41   40    4                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₆O₇

Average Mass

556.6550 Da

Monoisotopic Mass

556.24610 Da

IUPAC Name

(3aS,5aR,9R,10aR)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-5a-methyl-6-oxo-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]indene-3a-carboxylic acid

Traditional Name

(3aS,5aR,9R,10aR)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2H,3H,4H,5H,9H,10H,10aH-cyclohepta[e]indene-3a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2[C@H]3C[C@@H](OC(=O)C4=CC=CC=C4)C(COC(=O)C4=CC=CC=C4)=CC(=O)[C@]3(C)CC[C@]2(CC1)C(O)=O

InChI Identifier

InChI=1S/C34H36O7/c1-21(2)25-14-15-34(32(38)39)17-16-33(3)26(29(25)34)19-27(41-31(37)23-12-8-5-9-13-23)24(18-28(33)35)20-40-30(36)22-10-6-4-7-11-22/h4-13,18,21,26-27H,14-17,19-20H2,1-3H3,(H,38,39)/t26-,27-,33-,34+/m1/s1

InChI Key

BHACRICJKFFIAH-ABENWPRUSA-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
Sarcodon scabrosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	7.08	ChemAxon
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	154.55 m³·mol⁻¹	ChemAxon
Polarizability	59.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

8228998

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10053438

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid (NP0270732)

MOL for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

3D MOL for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

3D SDF for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

3D-SDF for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

PDB for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

3D PDB for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

SMILES for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

INCHI for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

Structure for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)

3D Structure for NP0270732 ((3as,5ar,9r,10ar)-9-(benzoyloxy)-8-[(benzoyloxy)methyl]-1-isopropyl-5a-methyl-6-oxo-2h,3h,4h,5h,9h,10h,10ah-cyclohepta[e]indene-3a-carboxylic acid)