NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate (NP0270388)

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Record Information

Version

2.0

Created at

2022-09-08 16:15:46 UTC

Updated at

2022-09-08 16:15:46 UTC

NP-MRD ID

NP0270388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate

Description

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate is found in Siphoneugena densiflora. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]Hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082218152D          

 38 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082218152D          

 38 42  0  0  1  0            999 V2000
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 15 27  1  0  0  0  0
 27 28  1  1  0  0  0
 13 29  2  0  0  0  0
 29 30  1  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
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
 34 37  2  0  0  0  0
  5 37  1  0  0  0  0
 37 38  1  0  0  0  0
  9 38  1  0  0  0  0
 30 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0270388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C3C(=C1)C(=O)OC1=C(OC)C(O[C@@H]4O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]4O)=CC(C(=O)O2)=C31

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O14/c1-7(25)34-6-12-15(26)17(28)18(29)24(36-12)35-11-5-9-14-13-8(23(31)38-21(14)19(11)33-3)4-10(32-2)16(27)20(13)37-22(9)30/h4-5,12,15,17-18,24,26-29H,6H2,1-3H3/t12-,15-,17+,18-,24-/m1/s1

> <INCHI_KEY>
RQIKJFPMCUEYIW-BMMFWZCSSA-N

> <FORMULA>
C24H22O14

> <MOLECULAR_WEIGHT>
534.426

> <EXACT_MASS>
534.100955388

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
49.9143465956527

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
0.13076784699999983

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202755612647852

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.678433585013792

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6053089976762207

> <JCHEM_POLAR_SURFACE_AREA>
196.73999999999998

> <JCHEM_REFRACTIVITY>
120.86809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4(16),5,7,11,13-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      11.137  -0.206   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.127  -4.207   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.183  -0.206   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.723  -0.206   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.493   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.033   1.127   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.803  -0.206   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.343  -0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.113  -1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.113   1.127   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.723   2.461   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.493   3.795   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.183   2.461   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.413   3.795   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.413   1.127   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.747   1.127   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   38                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   15   28                                                  
CONECT   28   27                                                            
CONECT   29   13   30                                                       
CONECT   30   29   31   38                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   37                                                  
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
CONECT   37   34    5   38                                                  
CONECT   38   37    9   30                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0,.0,]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl}oxy)oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₂₂O₁₄

Average Mass

534.4260 Da

Monoisotopic Mass

534.10096 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C3C(=C1)C(=O)OC1=C(OC)C(O[C@@H]4O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]4O)=CC(C(=O)O2)=C31

InChI Identifier

InChI=1S/C24H22O14/c1-7(25)34-6-12-15(26)17(28)18(29)24(36-12)35-11-5-9-14-13-8(23(31)38-21(14)19(11)33-3)4-10(32-2)16(27)20(13)37-22(9)30/h4-5,12,15,17-18,24,26-29H,6H2,1-3H3/t12-,15-,17+,18-,24-/m1/s1

InChI Key

RQIKJFPMCUEYIW-BMMFWZCSSA-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
Siphoneugena densiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
Phenolic glycoside
O-glycosyl compound
Isocoumarin
Glycosyl compound
Coumarin
2-benzopyran
1-benzopyran
Benzopyran
Anisole
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

162877399

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate (NP0270388)

MOL for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

3D MOL for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

3D SDF for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

3D-SDF for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

PDB for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

3D PDB for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

SMILES for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

INCHI for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

Structure for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)

3D Structure for NP0270388 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-({14-hydroxy-7,13-dimethoxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)oxan-2-yl]methyl acetate)