NP-MRD: Showing NP-Card for (2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal (NP0315423)

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Record Information

Version

2.0

Created at

2022-09-11 14:02:45 UTC

Updated at

2022-09-11 14:02:46 UTC

NP-MRD ID

NP0315423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal

Description

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112216022D          

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    2.6194   -1.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135   -1.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9939   -1.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8508   -0.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2383   -0.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480   -0.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407   -0.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2012   -1.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6536   -2.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0094   -1.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5571   -1.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5141    0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582    0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7463    1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    2.8017    0.0000 O   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  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 11 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 38  1  0  0  0  0
 24 38  1  0  0  0  0
 38 39  2  0  0  0  0
 22 40  1  0  0  0  0
  9 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0315423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C2=C(OC34C5CC(C=C3C2=O)C(=O)C4(C\C=C(/C)C=O)OC5(C)C)C2=C1OC(C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C33H38O8/c1-16(2)8-9-19-25(35)24-26(36)21-12-18-13-22-31(6,7)41-32(29(18)37,11-10-17(3)15-34)33(21,22)40-28(24)20-14-23(30(4,5)38)39-27(19)20/h8,10,12,15,18,22-23,35,38H,9,11,13-14H2,1-7H3/b17-10+

> <INCHI_KEY>
QDGCJQVVURTOBY-LICLKQGHSA-N

> <FORMULA>
C33H38O8

> <MOLECULAR_WEIGHT>
562.659

> <EXACT_MASS>
562.256668184

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
61.180764997492844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal

> <JCHEM_LOGP>
4.935883481000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.743016025823252

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.83837096740541

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106445799264229

> <JCHEM_POLAR_SURFACE_AREA>
119.35999999999999

> <JCHEM_REFRACTIVITY>
154.90950000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      14.186   8.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.938   6.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.130   5.821   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.498   6.251   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.241   4.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.071   3.547   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.626   4.078   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.345   5.630   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.443   3.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.706   1.574   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.152   1.043   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.335   2.030   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.638   1.210   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.262  -0.283   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.356  -1.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.190  -2.906   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.791  -3.060   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.860  -0.823   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.725  -0.386   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.443   0.634   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.789   0.822   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.908   2.487   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.561   3.382   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.454   2.247   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.508   1.063   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.270  -0.541   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.890  -2.055   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.372  -3.056   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.722  -3.328   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.455  -1.506   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.178  -0.066   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.690  -1.422   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.356  -1.763   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.842  -3.225   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.820  -4.376   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.351  -3.534   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.373  -2.382   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.826   0.811   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.229   0.770   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.993   3.670   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.658   5.230   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   40                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   14   11                                                       
CONECT   20   10   21                                                       
CONECT   21   20   22   26   31                                             
CONECT   22   21   23   40                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   38                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   21   32   38                                             
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   31   24   39                                                  
CONECT   39   38                                                            
CONECT   40   22    9   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₈O₈

Average Mass

562.6590 Da

Monoisotopic Mass

562.25667 Da

IUPAC Name

(2E)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C2=C(OC34C5CC(C=C3C2=O)C(=O)C4(C\C=C(/C)C=O)OC5(C)C)C2=C1OC(C2)C(C)(C)O

InChI Identifier

InChI=1S/C33H38O8/c1-16(2)8-9-19-25(35)24-26(36)21-12-18-13-22-31(6,7)41-32(29(18)37,11-10-17(3)15-34)33(21,22)40-28(24)20-14-23(30(4,5)38)39-27(19)20/h8,10,12,15,18,22-23,35,38H,9,11,13-14H2,1-7H3/b17-10+

InChI Key

QDGCJQVVURTOBY-LICLKQGHSA-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
Garcinia gaudichaudii	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	4.94	ChemAxon
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	154.91 m³·mol⁻¹	ChemAxon
Polarizability	61.18 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal (NP0315423)

MOL for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

3D MOL for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

3D SDF for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

3D-SDF for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

PDB for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

3D PDB for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

SMILES for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

INCHI for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

Structure for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)

3D Structure for NP0315423 ((2e)-4-[11-hydroxy-7-(2-hydroxypropan-2-yl)-20,20-dimethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4(12),5(9),10,14-tetraen-18-yl]-2-methylbut-2-enal)