NP-MRD: Showing NP-Card for 3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate (NP0246771)

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Record Information

Version

2.0

Created at

2022-09-07 08:20:58 UTC

Updated at

2022-09-07 08:20:58 UTC

NP-MRD ID

NP0246771

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate

Description

3-{[4-(Acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. 3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate is found in Cunninghamia lanceolata. 3-{[4-(Acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251516182D          

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M  END

     RDKit          3D

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  Mrv1533004251516182D          

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 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
 14 27  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  5 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC2COC(=O)C2(CC2=CC(OC)=C(OC(C)=O)C(OC)=C2)OC(C)=O)=CC=C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O11/c1-15(28)36-21-8-7-18(10-22(21)32-4)9-20-14-35-26(31)27(20,38-17(3)30)13-19-11-23(33-5)25(37-16(2)29)24(12-19)34-6/h7-8,10-12,20H,9,13-14H2,1-6H3

> <INCHI_KEY>
NLGFAMMBGBWNKW-UHFFFAOYSA-N

> <FORMULA>
C27H30O11

> <MOLECULAR_WEIGHT>
530.526

> <EXACT_MASS>
530.178811786

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.605613294798786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.5351133916666653

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4313667988391705

> <JCHEM_POLAR_SURFACE_AREA>
132.89000000000001

> <JCHEM_REFRACTIVITY>
131.0073

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       6.229  -8.876   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.693  -8.400   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.013  -6.894   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.869  -5.864   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.189  -4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.045  -3.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.580  -3.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.104  -5.267   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.564  -5.267   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.088  -3.803   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.624  -3.327   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.334  -2.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.578  -1.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.362  -0.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.606   1.111   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.390   2.437   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.634   3.779   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.094   3.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.930   2.421   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.714   3.746   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.958   5.088   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.418   5.104   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.742   6.413   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.686   1.079   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.226   1.063   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.010   2.388   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.902  -0.246   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.090  -1.556   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.630  -1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.386  -0.198   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.414  -2.865   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.654  -3.881   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.798  -4.912   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.478  -6.418   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.622  -7.449   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.302  -8.955   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.447  -9.986   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.838  -9.431   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13   28                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   14                                                       
CONECT   28   12   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    5   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₀O₁₁

Average Mass

530.5260 Da

Monoisotopic Mass

530.17881 Da

IUPAC Name

3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate

Traditional Name

3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(CC2COC(=O)C2(CC2=CC(OC)=C(OC(C)=O)C(OC)=C2)OC(C)=O)=CC=C1OC(C)=O

InChI Identifier

InChI=1S/C27H30O11/c1-15(28)36-21-8-7-18(10-22(21)32-4)9-20-14-35-26(31)27(20,38-17(3)30)13-19-11-23(33-5)25(37-16(2)29)24(12-19)34-6/h7-8,10-12,20H,9,13-14H2,1-6H3

InChI Key

NLGFAMMBGBWNKW-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
Cunninghamia lanceolata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Tetracarboxylic acid or derivatives
Phenol ester
Dimethoxybenzene
M-dimethoxybenzene
Methoxybenzene
Anisole
Phenol ether
Phenoxy compound
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.41	ALOGPS
logP	2.54	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	132.89 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	131.01 m³·mol⁻¹	ChemAxon
Polarizability	54.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate (NP0246771)

MOL for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

3D MOL for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

3D SDF for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

3D-SDF for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

PDB for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

3D PDB for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

SMILES for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

INCHI for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

Structure for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)

3D Structure for NP0246771 (3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]methyl}-4-{[4-(acetyloxy)-3-methoxyphenyl]methyl}-2-oxooxolan-3-yl acetate)