NP-MRD: Showing NP-Card for 4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone (NP0316158)

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Record Information

Version

2.0

Created at

2022-09-11 15:09:49 UTC

Updated at

2022-09-11 15:09:49 UTC

NP-MRD ID

NP0316158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone

Description

4,15-Dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]Triacont-8-ene-10,16,25,30-tetrone belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). 4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone is found in Physalis angulata. Based on a literature review very few articles have been published on 4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]Triacont-8-ene-10,16,25,30-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217092D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112217092D          

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    5.5301    0.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7115    0.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3906    1.1280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -0.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928    0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285    1.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283    2.5546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6062    1.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    0.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2071    1.4844    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
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 21 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
  4 38  1  0  0  0  0
 13 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC(=O)C3(O)CCC4C(CC(O)C56OC5C=CC(=O)C46C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O11/c1-22-9-17-24(3)28-18(22)19(31)27(39-28,35-10-13(22)20(32)36-17)12-8-15(30)26-16(37-26)5-4-14(29)23(26,2)11(12)6-7-25(28,34)21(33)38-24/h4-5,11-13,15-18,30,34H,6-10H2,1-3H3

> <INCHI_KEY>
HXMKMOICDMXZPI-UHFFFAOYSA-N

> <FORMULA>
C28H30O11

> <MOLECULAR_WEIGHT>
542.537

> <EXACT_MASS>
542.178811786

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.21239231511576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1^{1,20}.0^{2,12}.0^{5,7}.0^{5,11}.0^{15,19}.0^{18,23}.0^{21,26}]triacont-8-ene-10,16,25,30-tetrone

> <JCHEM_LOGP>
0.9990040273333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.528040989810728

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.67647886760197

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3030095424743795

> <JCHEM_POLAR_SURFACE_AREA>
158.19

> <JCHEM_REFRACTIVITY>
125.43859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1^{1,20}.0^{2,12}.0^{5,7}.0^{5,11}.0^{15,19}.0^{18,23}.0^{21,26}]triacont-8-ene-10,16,25,30-tetrone

> <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       1.865  -1.967   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.645  -1.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.382   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.863   1.101   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.953  -0.309   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.414  -1.945   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.461  -3.075   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.204  -2.345   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.498  -3.402   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.107  -3.227   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.825  -1.774   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.453  -1.148   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.324   0.847   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.851  -0.234   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.629  -0.325   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.672   0.809   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.365   2.006   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.128   3.344   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.923   2.126   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.132   1.176   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.337  -0.351   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.408  -1.579   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.007  -2.997   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.535  -3.188   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.134  -4.607   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.465  -1.960   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.064  -3.379   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.993  -2.151   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.922  -0.922   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.323   0.496   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.795   0.687   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.196   2.106   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.866  -0.541   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267   0.878   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   3.421   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.413   4.769   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.132   3.267   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.785   1.772   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.387   2.771   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   14                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   38                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15   22                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   17   38                                             
CONECT   14   13    2   15                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18   19   35                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   33                                                  
CONECT   22   21   11   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   33                                             
CONECT   27   26   28                                                       
CONECT   28   27   26   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   21   26   34                                             
CONECT   34   33                                                            
CONECT   35   17   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37    4   13   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₁₁

Average Mass

542.5370 Da

Monoisotopic Mass

542.17881 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC12OC(=O)C3(O)CCC4C(CC(O)C56OC5C=CC(=O)C46C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

InChI Identifier

InChI=1S/C28H30O11/c1-22-9-17-24(3)28-18(22)19(31)27(39-28,35-10-13(22)20(32)36-17)12-8-15(30)26-16(37-26)5-4-14(29)23(26,2)11(12)6-7-25(28,34)21(33)38-24/h4-5,11-13,15-18,30,34H,6-10H2,1-3H3

InChI Key

HXMKMOICDMXZPI-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
Physalis angulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Physalins and derivatives

Direct Parent

Physalins and derivatives

Alternative Parents

Substituents

Physalin skeleton
Delta valerolactone
Delta_valerolactone
Oxepane
Cyclohexenone
Ketal
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Oxane
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Acetal
Dialkyl ether
Carboxylic acid derivative
Oxirane
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

73816390

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone (NP0316158)

MOL for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

3D MOL for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

3D SDF for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

3D-SDF for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

PDB for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

3D PDB for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

SMILES for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

INCHI for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

Structure for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)

3D Structure for NP0316158 (4,15-dihydroxy-11,18,21-trimethyl-6,17,24,28,29-pentaoxanonacyclo[17.9.1.1¹,²⁰.0²,¹².0⁵,⁷.0⁵,¹¹.0¹⁵,¹⁹.0¹⁸,²³.0²¹,²⁶]triacont-8-ene-10,16,25,30-tetrone)