NP-MRD: Showing NP-Card for 12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione (NP0215102)

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Record Information

Version

2.0

Created at

2022-09-05 14:35:24 UTC

Updated at

2022-09-05 14:35:24 UTC

NP-MRD ID

NP0215102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione

Description

NSC644193 belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11. 12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione is found in Xanthium pungens. Based on a literature review very few articles have been published on NSC644193.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216352D          

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M  END

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  Mrv1652309052216352D          

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  3  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
  8 10  1  0  0  0  0
 10 11  1  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  1  0  0  0  0
 14 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
  6 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 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
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 29 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 25 37  1  0  0  0  0
 17 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215102

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2OC(=O)C3(OC4CC5C(CC(C)C4(O)C=C3C(C)=O)OC(=O)C5=C)C2CC=C1\C=C\C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O8/c1-14-10-24-21(9-8-19(14)7-6-16(3)30)29(27(33)36-24)22(18(5)31)13-28(34)15(2)11-23-20(12-25(28)37-29)17(4)26(32)35-23/h6-8,13-15,20-21,23-25,34H,4,9-12H2,1-3,5H3/b7-6+

> <INCHI_KEY>
BGZGKGJBTWDZQU-VOTSOKGWSA-N

> <FORMULA>
C29H34O8

> <MOLECULAR_WEIGHT>
510.583

> <EXACT_MASS>
510.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.06797311099291

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-2,3a,4,7,8,8a-hexahydro-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0^{3,7}]tetradecan]-11'-ene-2,5'-dione

> <JCHEM_LOGP>
2.8631520686666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.09370411546008

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.176457152725735

> <JCHEM_PKA_STRONGEST_BASIC>
-3.596417337624886

> <JCHEM_POLAR_SURFACE_AREA>
116.20000000000002

> <JCHEM_REFRACTIVITY>
135.22159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3aH-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0^{3,7}]tetradecan]-11'-ene-2,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.511   0.987   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.771  -0.531   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.151  -1.213   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.515  -0.497   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.929  -2.737   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.411  -2.997   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.792  -4.406   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.303  -4.801   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.013  -6.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.066  -3.883   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.005  -5.422   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.760  -4.699   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.401  -3.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.095  -4.792   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.735  -4.069   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.148  -6.331   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.347  -2.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.653  -1.621   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.013  -2.344   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.183  -1.343   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.695  -1.633   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.963  -3.112   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.438  -3.326   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.893  -2.004   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.616  -0.645   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.880   0.708   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.478   2.127   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.460   3.282   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.961   2.544   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.228   4.060   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.676   4.587   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.943   6.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.764   7.094   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.390   6.630   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.211   1.645   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.288   0.107   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.133  -0.912   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   19                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   22   37                                             
CONECT   18   17   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    2    6                                                  
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   25   17                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₈

Average Mass

510.5830 Da

Monoisotopic Mass

510.22537 Da

IUPAC Name

12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-2,3a,4,7,8,8a-hexahydro-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0^{3,7}]tetradecan]-11'-ene-2,5'-dione

Traditional Name

12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3aH-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0^{3,7}]tetradecan]-11'-ene-2,5'-dione

CAS Registry Number

Not Available

SMILES

CC1CC2OC(=O)C3(OC4CC5C(CC(C)C4(O)C=C3C(C)=O)OC(=O)C5=C)C2CC=C1\C=C\C(C)=O

InChI Identifier

InChI=1S/C29H34O8/c1-14-10-24-21(9-8-19(14)7-6-16(3)30)29(27(33)36-24)22(18(5)31)13-28(34)15(2)11-23-20(12-25(28)37-29)17(4)26(32)35-23/h6-8,13-15,20-21,23-25,34H,4,9-12H2,1-3,5H3/b7-6+

InChI Key

BGZGKGJBTWDZQU-VOTSOKGWSA-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
Xanthium pungens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthanolides. These are sesquiterpenoids with a structure based on the xanthanolide skeleton consistsing of a cycloheptane ring usually attached to a four-carbon chain (at carbon 1 ) and a methyl group (at carbon 10), and fused to a five-member lactone ring (sharing carbons 7 and 8). The lactone ring can be conjugated with a methyl or methylene group at position 11.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Xanthanolides

Alternative Parents

Substituents

Xanthanolide-skeleton
Sesquiterpenoid
Dicarboxylic acid or derivatives
Pyran
Gamma butyrolactone
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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
logP	2.86	ChemAxon
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	116.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	135.22 m³·mol⁻¹	ChemAxon
Polarizability	54.07 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	No	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

4747828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5918884

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione (NP0215102)

MOL for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

3D MOL for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

3D SDF for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

3D-SDF for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

PDB for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

3D PDB for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

SMILES for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

INCHI for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

Structure for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)

3D Structure for NP0215102 (12'-acetyl-10'-hydroxy-7,9'-dimethyl-4'-methylidene-6-[(1e)-3-oxobut-1-en-1-yl]-4,7,8,8a-tetrahydro-3ah-6',14'-dioxaspiro[cyclohepta[b]furan-3,13'-tricyclo[8.4.0.0³,⁷]tetradecan]-11'-ene-2,5'-dione)