NP-MRD: Showing NP-Card for (1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate (NP0194838)

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Record Information

Version

2.0

Created at

2022-09-04 12:35:13 UTC

Updated at

2022-09-04 12:35:13 UTC

NP-MRD ID

NP0194838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate

Description

(1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-13-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]Octadec-17-en-2-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate is found in Briareum violaceum. Based on a literature review very few articles have been published on (1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-13-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]Octadec-17-en-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214352D          

 35 38  0  0  1  0            999 V2000
    2.4491    0.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7821   -0.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -0.2773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8093    0.5570    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2582   -0.7833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9408   -0.3200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5924   -0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323   -0.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042214352D          

 35 38  0  0  1  0            999 V2000
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 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 34  1  6  0  0  0
  2 35  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H]3O[C@H]3[C@H](OC(C)=O)[C@]3(C)C=CC(=O)[C@@](C)(O)[C@@H]3[C@H](OC(C)=O)[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO10/c1-9-14(25)18-24(31,10(2)21(29)35-18)20(33-12(4)27)17-22(5,8-7-13(28)23(17,6)30)19(32-11(3)26)16-15(9)34-16/h7-8,10,14-20,30-31H,1H2,2-6H3/t10-,14-,15+,16+,17+,18-,19-,20-,22+,23+,24+/m0/s1

> <INCHI_KEY>
ZMZWRXWIJZDCCP-UQRQEXTGSA-N

> <FORMULA>
C24H29ClO10

> <MOLECULAR_WEIGHT>
512.94

> <EXACT_MASS>
512.1449248

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.19702636523911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

> <JCHEM_LOGP>
0.7489085633333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.041722627120198

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.262119929293156

> <JCHEM_PKA_STRONGEST_BASIC>
-3.704040437861374

> <JCHEM_POLAR_SURFACE_AREA>
148.96000000000004

> <JCHEM_REFRACTIVITY>
118.3569

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

> <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       4.572   1.008   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.193  -0.468   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.732  -0.518   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       7.111   1.040   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       7.949  -1.462   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.223  -0.597   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.439  -1.542   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.820  -0.706   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.917  -2.991   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.564  -3.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.377  -2.941   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.646  -4.049   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.855  -4.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.918  -6.220   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.542  -7.885   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.046  -8.655   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.058  -8.919   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.581  -5.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.308  -6.612   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.274  -5.395   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.331  -7.824   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.495  -7.921   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.999  -9.781   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.956  -7.871   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.229  -6.514   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.041  -5.205   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.415  -5.629   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.825  -4.261   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.076  -4.206   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.425  -3.846   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.830  -4.856   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.708  -2.714   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.396  -2.782   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.403  -1.605   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.919  -1.333   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   26                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35                                                  
CONECT   34   33   35                                                       
CONECT   35   34    2   33                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-13-(Acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0,.0,]octadec-17-en-2-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₉ClO₁₀

Average Mass

512.9400 Da

Monoisotopic Mass

512.14492 Da

IUPAC Name

(1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

Traditional Name

(1R,2R,3R,5R,7S,8R,11R,12S,13S,14S,15S)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0^{3,5}.0^{8,12}]octadec-17-en-13-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)C(=C)[C@H]3O[C@H]3[C@H](OC(C)=O)[C@]3(C)C=CC(=O)[C@@](C)(O)[C@@H]3[C@H](OC(C)=O)[C@@]12O

InChI Identifier

InChI=1S/C24H29ClO10/c1-9-14(25)18-24(31,10(2)21(29)35-18)20(33-12(4)27)17-22(5,8-7-13(28)23(17,6)30)19(32-11(3)26)16-15(9)34-16/h7-8,10,14-20,30-31H,1H2,2-6H3/t10-,14-,15+,16+,17+,18-,19-,20-,22+,23+,24+/m0/s1

InChI Key

ZMZWRXWIJZDCCP-UQRQEXTGSA-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
Briareum violaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Cyclohexenone
Gamma butyrolactone
Acyloin
Tetrahydrofuran
Tertiary alcohol
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	0.75	ChemAxon
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	148.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.36 m³·mol⁻¹	ChemAxon
Polarizability	48.2 Å³	ChemAxon
Number of Rings	4	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

162908110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate (NP0194838)

MOL for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

3D MOL for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

3D SDF for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

3D-SDF for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

PDB for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

3D PDB for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

SMILES for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

INCHI for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

Structure for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)

3D Structure for NP0194838 ((1r,2r,3r,5r,7s,8r,11r,12s,13s,14s,15s)-2-(acetyloxy)-7-chloro-12,15-dihydroxy-1,11,15-trimethyl-6-methylidene-10,16-dioxo-4,9-dioxatetracyclo[12.4.0.0³,⁵.0⁸,¹²]octadec-17-en-13-yl acetate)