NP-MRD: Showing NP-Card for 4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate (NP0172217)

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Record Information

Version

2.0

Created at

2022-09-03 09:04:21 UTC

Updated at

2022-09-03 09:04:21 UTC

NP-MRD ID

NP0172217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate

Description

4-(Dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]Dodeca-1(12),8,10-trien-3-yl acetate belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton. 4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate is found in Aglaia odorata. 4-(Dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]Dodeca-1(12),8,10-trien-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151514292D          

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M  END

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M  END


  Mrv1533004151514292D          

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    0.1547    0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4754    1.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940    1.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    0.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505   -1.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -1.1203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949   -2.4703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7248   -3.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0154   -2.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29 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
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C12OC3=CC(OC)=CC(OC)=C3C1(O)C(OC(C)=O)C(C2C1=CC=CC=C1)C(=O)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H33NO8/c1-18(33)39-28-25(29(34)32(2)3)26(19-10-8-7-9-11-19)31(20-12-14-21(36-4)15-13-20)30(28,35)27-23(38-6)16-22(37-5)17-24(27)40-31/h7-17,25-26,28,35H,1-6H3

> <INCHI_KEY>
OKCNLANNJAHRLR-UHFFFAOYSA-N

> <FORMULA>
C31H33NO8

> <MOLECULAR_WEIGHT>
547.604

> <EXACT_MASS>
547.220617027

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.55308451136105

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
2.829656952333335

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.91333691819042

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.603125210582686

> <JCHEM_PKA_STRONGEST_BASIC>
-1.719725509150431

> <JCHEM_POLAR_SURFACE_AREA>
103.76

> <JCHEM_REFRACTIVITY>
145.41299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       6.413   5.865   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.094   5.069   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.125   3.529   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.473   2.785   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.504   1.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.185   0.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.837   1.193   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.806   2.733   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.216  -1.090   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.444  -0.161   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.707  -1.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.207  -0.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.260  -1.815   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.759  -1.465   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.812  -2.589   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.813  -3.289   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.313  -3.639   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.866  -5.112   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.919  -6.236   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.260  -2.515   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.720  -2.545   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.225  -4.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.493  -3.475   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.523  -5.014   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.205  -5.811   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.235  -7.350   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.856  -5.067   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.229  -2.594   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.676  -1.121   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.746   0.107   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.218  -0.084   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.289   1.144   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.887   2.563   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.415   2.754   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.345   1.526   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.774  -3.099   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.610  -2.091   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0       1.484  -4.611   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       1.353  -6.146   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.029  -5.116   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   21   29                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   11   21                                                  
CONECT   21   20    9   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   36                                                  
CONECT   29   28    9   30                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   28   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
4-(Dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0,]dodeca-1(12),8,10-trien-3-yl acetic acid	Generator
4-(Dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetic acid	Generator

Chemical Formula

C₃₁H₃₃NO₈

Average Mass

547.6040 Da

Monoisotopic Mass

547.22062 Da

IUPAC Name

4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate

Traditional Name

4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C12OC3=CC(OC)=CC(OC)=C3C1(O)C(OC(C)=O)C(C2C1=CC=CC=C1)C(=O)N(C)C

InChI Identifier

InChI=1S/C31H33NO8/c1-18(33)39-28-25(29(34)32(2)3)26(19-10-8-7-9-11-19)31(20-12-14-21(36-4)15-13-20)30(28,35)27-23(38-6)16-22(37-5)17-24(27)40-31/h7-17,25-26,28,35H,1-6H3

InChI Key

OKCNLANNJAHRLR-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
Aglaia odorata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavaglines. These are heterocyclic compounds with a structure characterized by a cyclopenta[b]benzofuran skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Flavaglines

Direct Parent

Flavaglines

Alternative Parents

Substituents

Flavagline skeleton
Stilbene
Coumaran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary carboxylic acid amide
Tertiary alcohol
Carboxamide group
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen 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	3.84	ALOGPS
logP	2.83	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	145.41 m³·mol⁻¹	ChemAxon
Polarizability	57.55 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

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

72977111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate (NP0172217)

MOL for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

3D MOL for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

3D SDF for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

3D-SDF for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

PDB for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

3D PDB for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

SMILES for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

INCHI for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

Structure for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)

3D Structure for NP0172217 (4-(dimethylcarbamoyl)-2-hydroxy-10,12-dimethoxy-6-(4-methoxyphenyl)-5-phenyl-7-oxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-yl acetate)