NP-MRD: Showing NP-Card for (1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate (NP0309703)

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Record Information

Version

2.0

Created at

2022-09-11 04:29:28 UTC

Updated at

2022-09-11 04:29:29 UTC

NP-MRD ID

NP0309703

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate

Description

(1R)-2-[(3R)-3-acetyl-2,2-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0¹,³]Undec-9-en-11-yl]ethyl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate is found in Carapa procera. Based on a literature review very few articles have been published on (1R)-2-[(3R)-3-acetyl-2,2-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0¹,³]Undec-9-en-11-yl]ethyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112206292D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112206292D          

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  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19  5  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  1  0  0  0
 35 37  1  0  0  0  0
 19 37  1  0  0  0  0
 24 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309703

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H](C[C@]1(C=CC(=O)OC1(C)C)C(C)=O)[C@]1(C)C=CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O9/c1-16(29)27(12-8-20(31)36-24(27,3)4)14-19(34-17(2)30)25(5)10-7-11-26(6)21(18-9-13-33-15-18)35-23(32)22-28(25,26)37-22/h7-10,12-13,15,19,21-22H,11,14H2,1-6H3/t19-,21+,22-,25+,26+,27-,28+/m1/s1

> <INCHI_KEY>
YUXXBKGBSUTVMC-GIAKCZLJSA-N

> <FORMULA>
C28H32O9

> <MOLECULAR_WEIGHT>
512.555

> <EXACT_MASS>
512.20463261

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.5034069939573

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-2-[(3R)-3-acetyl-2,2-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undec-9-en-11-yl]ethyl acetate

> <JCHEM_LOGP>
3.331523429999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.638636129516915

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8727130147063717

> <JCHEM_POLAR_SURFACE_AREA>
121.64000000000001

> <JCHEM_REFRACTIVITY>
129.7741

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-2-[(3R)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undec-9-en-11-yl]ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.251  -6.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.162  -4.996   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.590  -4.100   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.398  -3.683   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.417  -4.181   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.155  -5.627   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.214  -6.887   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.747  -6.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.585  -6.978   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.140  -4.995   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.548  -7.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.548  -9.197   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.214  -9.967   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.282 -11.585   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.119  -9.197   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.119  -7.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.496  -8.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.644  -7.241   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.429  -4.593   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.670   0.802   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.581   2.445   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.105   3.910   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.565   3.910   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.061  -3.114   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11   16                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    7   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5   20   21   37                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   37                                             
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27                                                       
CONECT   32   26   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35   37                                                       
CONECT   37   36   35   19   24                                             
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1R)-2-[(3R)-3-Acetyl-2,2-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0,]undec-9-en-11-yl]ethyl acetic acid	Generator

Chemical Formula

C₂₈H₃₂O₉

Average Mass

512.5550 Da

Monoisotopic Mass

512.20463 Da

IUPAC Name

(1R)-2-[(3R)-3-acetyl-2,2-dimethyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undec-9-en-11-yl]ethyl acetate

Traditional Name

(1R)-2-[(3R)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1R,3S,6R,7S,11S)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0^{1,3}]undec-9-en-11-yl]ethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H](C[C@]1(C=CC(=O)OC1(C)C)C(C)=O)[C@]1(C)C=CC[C@@]2(C)[C@@H](OC(=O)[C@H]3O[C@@]123)C1=COC=C1

InChI Identifier

InChI=1S/C28H32O9/c1-16(29)27(12-8-20(31)36-24(27,3)4)14-19(34-17(2)30)25(5)10-7-11-26(6)21(18-9-13-33-15-18)35-23(32)22-28(25,26)37-22/h7-10,12-13,15,19,21-22H,11,14H2,1-6H3/t19-,21+,22-,25+,26+,27-,28+/m1/s1

InChI Key

YUXXBKGBSUTVMC-GIAKCZLJSA-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
Carapa procera	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
1,4-dioxepane
Delta valerolactone
Dihydropyranone
Dioxepane
Delta_valerolactone
Oxane
Pyran
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
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	3.33	ChemAxon
pKa (Strongest Acidic)	18.64	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.77 m³·mol⁻¹	ChemAxon
Polarizability	50.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

10397053

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16047138

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate (NP0309703)

MOL for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

3D MOL for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

3D SDF for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

3D-SDF for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

PDB for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

3D PDB for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

SMILES for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

INCHI for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

Structure for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)

3D Structure for NP0309703 ((1r)-2-[(3r)-3-acetyl-2,2-dimethyl-6-oxopyran-3-yl]-1-[(1r,3s,6s,7s,11s)-6-(furan-3-yl)-7,11-dimethyl-4-oxo-2,5-dioxatricyclo[5.4.0.0?,?]undec-9-en-11-yl]ethyl acetate)