NP-MRD: Showing NP-Card for 22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione (NP0194375)

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Record Information

Version

2.0

Created at

2022-09-04 12:01:20 UTC

Updated at

2022-09-04 12:01:20 UTC

NP-MRD ID

NP0194375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione

Description

22-Hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]Tetracosane-8,2'-oxolane]-5',19-dione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione is found in Pseudolarix amabilis. Based on a literature review very few articles have been published on 22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]Tetracosane-8,2'-oxolane]-5',19-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214012D          

 37 43  0  0  0  0            999 V2000
    8.6980    0.5438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042214012D          

 37 43  0  0  0  0            999 V2000
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    1.6063    2.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444    3.3689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922    2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659    3.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4986    3.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9246    2.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974    3.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    2.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    2.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187    1.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6012    1.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9624    2.5478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5878    2.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3907    2.1996    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
  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
  6  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
 11 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 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  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 16 32  1  0  0  0  0
 32 33  1  0  0  0  0
  9 34  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0194375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2(CC(C)C3C(CC4(C)C5CCC6C7(O)CC5(CCC34C)OC7CC(=O)OC6(C)C)O2)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O7/c1-16-12-29(13-17(2)24(32)37-29)34-18-14-27(6)20-8-7-19-25(3,4)36-22(31)11-21-30(19,33)15-28(20,35-21)10-9-26(27,5)23(16)18/h16-21,23,33H,7-15H2,1-6H3

> <INCHI_KEY>
OZKGSSQUPKNYSU-UHFFFAOYSA-N

> <FORMULA>
C30H44O7

> <MOLECULAR_WEIGHT>
516.675

> <EXACT_MASS>
516.308703757

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.81669939576001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0^{1,13}.0^{4,12}.0^{5,10}.0^{16,22}]tetracosane-8,2'-oxolane]-5',19-dione

> <JCHEM_LOGP>
3.574477015333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.426524259448218

> <JCHEM_PKA_STRONGEST_BASIC>
-3.487038288917349

> <JCHEM_POLAR_SURFACE_AREA>
91.29000000000002

> <JCHEM_REFRACTIVITY>
134.0634

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0^{1,13}.0^{4,12}.0^{5,10}.0^{16,22}]tetracosane-8,2'-oxolane]-5',19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      16.236   1.015   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.436   2.331   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.901   2.457   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.547   3.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.352   5.483   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.931   6.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.735   7.605   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.706   5.145   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.901   3.617   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.509   2.959   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.453   4.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.858   2.659   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.917   4.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.596   2.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.173   1.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.814   2.467   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.501   1.638   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.594   0.553   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.688   0.331   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.050   2.137   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.527   3.627   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.004   3.795   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.366   4.972   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.998   5.290   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.376   6.289   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.959   5.472   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.843   6.785   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.397   6.766   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.193   5.431   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.075   6.693   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.051   4.713   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.751   4.021   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.275   3.584   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.322   3.023   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      14.863   4.756   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.031   3.752   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      17.529   4.106   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34   35                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   29                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   13   27   31                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    8   11   30                                             
CONECT   30   29                                                            
CONECT   31   26   32                                                       
CONECT   32   31   24   16   33                                             
CONECT   33   32                                                            
CONECT   34    9    4                                                       
CONECT   35    4   36                                                       
CONECT   36   35    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₇

Average Mass

516.6750 Da

Monoisotopic Mass

516.30870 Da

IUPAC Name

22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0^{1,13}.0^{4,12}.0^{5,10}.0^{16,22}]tetracosane-8,2'-oxolane]-5',19-dione

Traditional Name

22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0^{1,13}.0^{4,12}.0^{5,10}.0^{16,22}]tetracosane-8,2'-oxolane]-5',19-dione

CAS Registry Number

Not Available

SMILES

CC1CC2(CC(C)C3C(CC4(C)C5CCC6C7(O)CC5(CCC34C)OC7CC(=O)OC6(C)C)O2)OC1=O

InChI Identifier

InChI=1S/C30H44O7/c1-16-12-29(13-17(2)24(32)37-29)34-18-14-27(6)20-8-7-19-25(3,4)36-22(31)11-21-30(19,33)15-28(20,35-21)10-9-26(27,5)23(16)18/h16-21,23,33H,7-15H2,1-6H3

InChI Key

OZKGSSQUPKNYSU-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
Pseudolarix amabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Pinguisane sesquiterpenoid
Caprolactone
Ketal
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
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	3.57	ChemAxon
pKa (Strongest Acidic)	13.43	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	134.06 m³·mol⁻¹	ChemAxon
Polarizability	56.82 Å³	ChemAxon
Number of Rings	7	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

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

163192823

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione (NP0194375)

MOL for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

3D MOL for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

3D SDF for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

3D-SDF for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

PDB for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

3D PDB for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

SMILES for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

INCHI for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

Structure for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)

3D Structure for NP0194375 (22-hydroxy-4,4',6,12,17,17-hexamethyl-9,18,24-trioxaspiro[hexacyclo[19.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰.0¹⁶,²²]tetracosane-8,2'-oxolane]-5',19-dione)