NP-MRD: Showing NP-Card for {2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate (NP0318848)

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Record Information

Version

2.0

Created at

2022-09-11 19:34:46 UTC

Updated at

2022-09-11 19:34:46 UTC

NP-MRD ID

NP0318848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

{2-[4-(Acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. {2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate is found in Araucaria angustifolia. Based on a literature review very few articles have been published on {2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112221342D          

 33 35  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -5.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -5.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938   -4.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -3.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3068   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653    0.4014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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    8.1213   -1.3337   -0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -0.1919   -1.3184 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6244   -1.2993    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491   -2.5759    0.1545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7149   -3.3807   -0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404   -0.8187    0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    1.3875    0.2641 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0013    2.8963    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    3.4772    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112221342D          

 33 35  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0318848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2COC(C2COC(C)=O)C2=CC=C(OC(C)=O)C(OC)=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O8/c1-15(26)31-14-20-19(10-17-6-8-21(28-3)23(11-17)29-4)13-32-25(20)18-7-9-22(33-16(2)27)24(12-18)30-5/h6-9,11-12,19-20,25H,10,13-14H2,1-5H3

> <INCHI_KEY>
VZPHBGQRBYHTQG-UHFFFAOYSA-N

> <FORMULA>
C25H30O8

> <MOLECULAR_WEIGHT>
458.507

> <EXACT_MASS>
458.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.18750390206492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.803156077333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9814716315672602

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000002

> <JCHEM_REFRACTIVITY>
119.97890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
{2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl 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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.104  -4.680   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.057  -9.663   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.589  -9.502   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.494 -10.748   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.215  -8.096   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.310  -6.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.936  -5.443   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.162  -0.757   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.306  -1.788   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.482   0.749   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   12                                                       
CONECT   24   11    8   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    6   31                                                       
CONECT   31   30    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₅H₃₀O₈

Average Mass

458.5070 Da

Monoisotopic Mass

458.19407 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2COC(C2COC(C)=O)C2=CC=C(OC(C)=O)C(OC)=C2)C=C1OC

InChI Identifier

InChI=1S/C25H30O8/c1-15(26)31-14-20-19(10-17-6-8-21(28-3)23(11-17)29-4)13-32-25(20)18-7-9-22(33-16(2)27)24(12-18)30-5/h6-9,11-12,19-20,25H,10,13-14H2,1-5H3

InChI Key

VZPHBGQRBYHTQG-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
Araucaria angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
O-dimethoxybenzene
Dimethoxybenzene
Phenol ester
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.8	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	119.98 m³·mol⁻¹	ChemAxon
Polarizability	49.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

73830431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate (NP0318848)

MOL for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

3D MOL for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

3D SDF for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

3D-SDF for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

PDB for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

3D PDB for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

SMILES for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

INCHI for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

Structure for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)

3D Structure for NP0318848 ({2-[4-(acetyloxy)-3-methoxyphenyl]-4-[(3,4-dimethoxyphenyl)methyl]oxolan-3-yl}methyl acetate)