NP-MRD: Showing NP-Card for (1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione (NP0189208)

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Record Information

Version

2.0

Created at

2022-09-04 05:39:23 UTC

Updated at

2022-09-04 05:39:23 UTC

NP-MRD ID

NP0189208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione

Description

(1S,3R,4S,7R,8R,9R,11S,14S,26S)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacosa-16,20,22-triene-5,10,24-trione belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione is found in Schisandra sphenanthera. Based on a literature review very few articles have been published on (1S,3R,4S,7R,8R,9R,11S,14S,26S)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacosa-16,20,22-triene-5,10,24-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207392D          

 35 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042207392D          

 35 41  0  0  1  0            999 V2000
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 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 21 18  1  1  0  0  0
  6 21  1  0  0  0  0
 22 21  1  6  0  0  0
 14 22  1  0  0  0  0
  9 22  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  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
 27 30  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0189208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2O[C@]34O[C@@]5(CC[C@@]6(C)[C@@H]3[C@H]([C@H]2OC1=O)[C@@](C)(O)C6=O)CC1=COC(C)(C)C1=CC=C5C4=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O8/c1-12-17-18(33-21(12)29)16-19-24(4,22(30)25(16,5)31)8-9-26-10-13-11-32-23(2,3)14(13)6-7-15(26)20(28)27(19,34-17)35-26/h6-7,11-12,16-19,31H,8-10H2,1-5H3/t12-,16-,17+,18+,19-,24-,25+,26-,27-/m0/s1

> <INCHI_KEY>
NTTNNBFBFNBAKE-IRELMZGISA-N

> <FORMULA>
C27H30O8

> <MOLECULAR_WEIGHT>
482.529

> <EXACT_MASS>
482.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.02537893208001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,7R,8R,9R,11S,14S,26S)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16,20,22-triene-5,10,24-trione

> <JCHEM_LOGP>
2.496121009333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.928713866143895

> <JCHEM_PKA_STRONGEST_BASIC>
-3.70478055494866

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
123.06419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,7R,8R,9R,11S,14S,26S)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16,20,22-triene-5,10,24-trione

> <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       4.645  -1.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.530  -3.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.219  -3.863   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.795  -3.279   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.584  -5.359   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.120  -5.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.704  -4.050   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.247  -3.873   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.322  -5.040   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.739  -5.437   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.102  -5.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.047  -7.150   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.872  -8.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.287  -7.986   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.697  -9.471   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.076  -9.021   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.224 -10.554   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.723  -8.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.102  -9.664   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.259  -7.778   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.056  -6.728   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.624  -6.531   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.671  -5.852   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.986  -5.026   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.399  -5.639   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.419  -4.485   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.636  -3.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.037  -2.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.147  -1.698   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.133  -3.493   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.042  -2.389   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.515  -2.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.720  -3.883   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.136  -3.635   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.473  -2.245   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22   34                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   23   33                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18    6   22                                                  
CONECT   22   21   14    9                                                  
CONECT   23   11   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   24   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   11   34                                                  
CONECT   34   33    9   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₈

Average Mass

482.5290 Da

Monoisotopic Mass

482.19407 Da

IUPAC Name

(1S,3R,4S,7R,8R,9R,11S,14S,26S)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16,20,22-triene-5,10,24-trione

Traditional Name

(1S,3R,4S,7R,8R,9R,11S,14S,26S)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16,20,22-triene-5,10,24-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2O[C@]34O[C@@]5(CC[C@@]6(C)[C@@H]3[C@H]([C@H]2OC1=O)[C@@](C)(O)C6=O)CC1=COC(C)(C)C1=CC=C5C4=O

InChI Identifier

InChI=1S/C27H30O8/c1-12-17-18(33-21(12)29)16-19-24(4,22(30)25(16,5)31)8-9-26-10-13-11-32-23(2,3)14(13)6-7-15(26)20(28)27(19,34-17)35-26/h6-7,11-12,16-19,31H,8-10H2,1-5H3/t12-,16-,17+,18+,19-,24-,25+,26-,27-/m0/s1

InChI Key

NTTNNBFBFNBAKE-IRELMZGISA-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
Schisandra sphenanthera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Ketal
Oxepane
Pyran
Oxane
Gamma butyrolactone
3-furanone
Acyloin
Tetrahydrofuran
Tertiary alcohol
Furan
Dihydrofuran
Cyclic alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.5	ChemAxon
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	123.06 m³·mol⁻¹	ChemAxon
Polarizability	50.03 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

162942675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione (NP0189208)

MOL for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

3D MOL for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

3D SDF for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

3D-SDF for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

PDB for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

3D PDB for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

SMILES for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

INCHI for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

Structure for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)

3D Structure for NP0189208 ((1s,3r,4s,7r,8r,9r,11s,14s,26s)-9-hydroxy-4,9,11,19,19-pentamethyl-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]hexacosa-16,20,22-triene-5,10,24-trione)