NP-MRD: Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate (NP0162336)

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Record Information

Version

2.0

Created at

2022-09-02 20:42:16 UTC

Updated at

2022-09-02 20:42:16 UTC

NP-MRD ID

NP0162336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

Description

Marshmine belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Marshmine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Marshmine has been detected, but not quantified in, citrus. 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate is found in Physalis angulata. This could make marshmine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241215592D          

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M  END

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M  END


  Mrv0541 02241215592D          

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    2.1756    2.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4593    2.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066    0.8580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6053    2.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  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
  4  7  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  1  0  0  0  0
 16 17  2  0  0  0  0
 17 27  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  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
 29 34  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 35  2  0  0  0  0
 32 33  2  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 33 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CC(C)=C(C)C(=O)O1)C1=CC(OC(C)=O)C2(O)C3CC4OC44CC=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O7/c1-15-12-22(36-26(33)16(15)2)17(3)20-13-25(35-18(4)31)30(34)21-14-24-29(37-24)10-7-8-23(32)28(29,6)19(21)9-11-27(20,30)5/h7-8,13,17,19,21-22,24-25,34H,9-12,14H2,1-6H3

> <INCHI_KEY>
GPTVOZHQPZXWDW-UHFFFAOYSA-N

> <FORMULA>
C30H38O7

> <MOLECULAR_WEIGHT>
510.6185

> <EXACT_MASS>
510.26175357

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
55.706672529108126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
3.816945164999998

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.651463060738514

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.1231182919588

> <JCHEM_PKA_STRONGEST_BASIC>
-3.613805574420808

> <JCHEM_POLAR_SURFACE_AREA>
102.43

> <JCHEM_REFRACTIVITY>
136.8726

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.732  -2.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.732  -4.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.398  -5.029   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.066  -4.258   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.066  -2.715   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.398  -1.946   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.732  -5.029   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.400  -4.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.400  -2.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.732  -1.946   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.071  -1.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.071  -0.411   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.400   0.355   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.732  -0.411   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.387  -2.419   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.284  -1.178   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.387   0.059   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.398  -0.404   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.066  -5.800   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.066  -1.172   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.071  -3.489   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.071   1.131   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.786  -3.911   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.123  -4.682   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.459  -3.911   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.123  -6.225   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.387   1.602   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.050   2.373   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.724   2.373   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.061   1.602   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.395   2.373   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.395   3.913   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.061   4.682   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.724   3.913   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.732   1.602   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.061   6.225   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.730   4.684   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6   10   20                                             
CONECT    6    1    5   18                                                  
CONECT    7    4    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   21                                             
CONECT   12   11   13   17   22                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16   27                                                  
CONECT   18    6                                                            
CONECT   19    4    7                                                       
CONECT   20    5                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   15   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   17   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   29   33                                                       
CONECT   35   31                                                            
CONECT   36   33                                                            
CONECT   37   32                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
(-)-Marshmine	HMDB
1,5-Dihydroxy-4-(2-hydroxy-3-methyl-3-butenyl)-3-methoxy-10-methylacridone	HMDB
15-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetic acid	Generator

Chemical Formula

C₃₀H₃₈O₇

Average Mass

510.6185 Da

Monoisotopic Mass

510.26175 Da

IUPAC Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

Traditional Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C1CC(C)=C(C)C(=O)O1)C1=CC(OC(C)=O)C2(O)C3CC4OC44CC=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C30H38O7/c1-15-12-22(36-26(33)16(15)2)17(3)20-13-25(35-18(4)31)30(34)21-14-24-29(37-24)10-7-8-23(32)28(29,6)19(21)9-11-27(20,30)5/h7-8,13,17,19,21-22,24-25,34H,9-12,14H2,1-6H3

InChI Key

GPTVOZHQPZXWDW-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 acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Dihydroquinolone
8-hydroxyquinoline
Dihydroquinoline
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Azacycle
Alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
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
logP	4.16	ALOGPS
logP	3.82	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.12	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.87 m³·mol⁻¹	ChemAxon
Polarizability	55.71 Å³	ChemAxon
Number of Rings	6	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

HMDB0041046

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020919

KNApSAcK ID

C00024218

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

101696941

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate (NP0162336)

MOL for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D MOL for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D SDF for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D-SDF for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

PDB for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D PDB for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

SMILES for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

INCHI for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

Structure for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D Structure for NP0162336 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)