NP-MRD: Showing NP-Card for [2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate (NP0181731)

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Record Information

Version

2.0

Created at

2022-09-03 20:18:17 UTC

Updated at

2022-09-03 20:18:17 UTC

NP-MRD ID

NP0181731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate

Description

[2-(4-Hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. [2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate is found in Tanacetum sinaicum. [2-(4-Hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201500072D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201500072D          

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    3.5635   -0.7930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    0.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -0.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069    0.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4214   -0.7930    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
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  2  0  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 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  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0181731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(C(COC(=O)CC(C)C)C2=CC(C=CCOC(=O)CC(C)C)=C1)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O8/c1-18(2)12-27(32)36-11-7-8-20-14-22-23(17-37-28(33)13-19(3)4)29(38-30(22)26(15-20)35-6)21-9-10-24(31)25(16-21)34-5/h7-10,14-16,18-19,23,29,31H,11-13,17H2,1-6H3

> <INCHI_KEY>
HZUKVQHPHZPOEM-UHFFFAOYSA-N

> <FORMULA>
C30H38O8

> <MOLECULAR_WEIGHT>
526.626

> <EXACT_MASS>
526.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.09510462137541

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate

> <ALOGPS_LOGP>
6.88

> <JCHEM_LOGP>
5.579710271

> <ALOGPS_LOGS>
-5.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.909974160569087

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4368873017907795

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000001

> <JCHEM_REFRACTIVITY>
144.3129

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.616  -9.116   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.472  -8.085   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.792  -6.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.648  -5.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.968  -4.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.433  -3.566   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.577  -4.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.257  -6.103   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.401  -7.134   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.823  -3.012   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.317  -3.332   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.547  -1.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.041  -1.678   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.990  -2.823   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.496  -2.502   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.435  -0.214   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.595   0.931   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.119   2.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.150   3.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.674   5.005   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.832   5.325   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.308   6.789   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.278   7.934   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.815   7.110   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.290   8.574   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.797   8.894   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.260   9.719   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.102   0.611   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.578  -0.854   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.984  -1.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.318  -0.710   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.652  -1.480   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.986  -0.710   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.986   0.830   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.319  -1.480   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.653  -0.710   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.653   0.830   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.987  -1.480   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   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   17   29                                                       
CONECT   29   28   12   30                                                  
CONECT   30   29   10   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   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
[2-(4-Hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoic acid	Generator

Chemical Formula

C₃₀H₃₈O₈

Average Mass

526.6260 Da

Monoisotopic Mass

526.25667 Da

IUPAC Name

[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate

Traditional Name

[2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

COC1=C2OC(C(COC(=O)CC(C)C)C2=CC(C=CCOC(=O)CC(C)C)=C1)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C30H38O8/c1-18(2)12-27(32)36-11-7-8-20-14-22-23(17-37-28(33)13-19(3)4)29(38-30(22)26(15-20)35-6)21-9-10-24(31)25(16-21)34-5/h7-10,14-16,18-19,23,29,31H,11-13,17H2,1-6H3

InChI Key

HZUKVQHPHZPOEM-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
Tanacetum sinaicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Methoxyphenol
Benzofuran
Coumaran
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	6.88	ALOGPS
logP	5.58	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	144.31 m³·mol⁻¹	ChemAxon
Polarizability	59.1 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 [2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate (NP0181731)

MOL for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

3D MOL for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

3D SDF for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

3D-SDF for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

PDB for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

3D PDB for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

SMILES for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

INCHI for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

Structure for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)

3D Structure for NP0181731 ([2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-{3-[(3-methylbutanoyl)oxy]prop-1-en-1-yl}-2,3-dihydro-1-benzofuran-3-yl]methyl 3-methylbutanoate)