NP-MRD: Showing NP-Card for 4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate (NP0197718)

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Record Information

Version

2.0

Created at

2022-09-04 16:01:50 UTC

Updated at

2022-09-04 16:01:50 UTC

NP-MRD ID

NP0197718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate

Description

4-(Benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. 4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate is found in Monteverdia apurimacensis. 4-(Benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251511262D          

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M  END

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M  END


  Mrv1533004251511262D          

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   -0.1914   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -4.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -6.0474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -6.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039   -5.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164   -6.0474    0.0000 O   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  1  0  0  0  0
  8  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
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  8 19  1  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  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 31 39  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC(COC(=O)C2=CC=CC=C2)C(COC(=O)C2=CC=CC=C2)CC2=CC=C(O)C(OC)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H34O8/c1-39-31-16-14-23(19-30(31)36)17-27(21-41-33(37)25-9-5-3-6-10-25)28(18-24-13-15-29(35)32(20-24)40-2)22-42-34(38)26-11-7-4-8-12-26/h3-16,19-20,27-28,35-36H,17-18,21-22H2,1-2H3

> <INCHI_KEY>
XDDSQSSDBMRHJP-UHFFFAOYSA-N

> <FORMULA>
C34H34O8

> <MOLECULAR_WEIGHT>
570.638

> <EXACT_MASS>
570.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
61.04528547940369

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(benzoyloxy)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate

> <ALOGPS_LOGP>
6.04

> <JCHEM_LOGP>
7.32346078

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.22631099658667

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.62322041919169

> <JCHEM_PKA_STRONGEST_BASIC>
-4.586138420922727

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
158.931

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(benzoyloxy)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate

> <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     -10.367  -9.955   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.597  -8.621   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.057  -8.621   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.287  -7.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.747  -7.287   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.977  -8.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.437  -8.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.437  -5.954   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.437  -3.286   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -1.953   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.977  -3.286   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.747  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.287  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.057  -3.286   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.287  -1.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.747  -1.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.127  -7.287   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.357  -5.954   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.183  -5.954   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.953  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.493  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.183  -3.286   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.357  -3.286   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.127  -1.953   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.357  -0.619   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.183  -0.619   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.953  -1.953   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.357  -8.621   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.183  -8.621   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.953  -7.287   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.493  -7.287   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.263  -8.621   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.803  -8.621   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.493  -9.955   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.263 -11.288   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.493 -12.622   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.953  -9.955   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.747  -9.955   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -7.287  -9.955   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.057 -11.288   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    8   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   19   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   31                                                       
CONECT   40    6   41                                                       
CONECT   41   40    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
4-(Benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoic acid	Generator

Chemical Formula

C₃₄H₃₄O₈

Average Mass

570.6380 Da

Monoisotopic Mass

570.22537 Da

IUPAC Name

4-(benzoyloxy)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate

Traditional Name

4-(benzoyloxy)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC(COC(=O)C2=CC=CC=C2)C(COC(=O)C2=CC=CC=C2)CC2=CC=C(O)C(OC)=C2)C=C1O

InChI Identifier

InChI=1S/C34H34O8/c1-39-31-16-14-23(19-30(31)36)17-27(21-41-33(37)25-9-5-3-6-10-25)28(18-24-13-15-29(35)32(20-24)40-2)22-42-34(38)26-11-7-4-8-12-26/h3-16,19-20,27-28,35-36H,17-18,21-22H2,1-2H3

InChI Key

XDDSQSSDBMRHJP-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
Monteverdia apurimacensis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
Benzoate ester
Methoxyphenol
Benzoic acid or derivatives
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6.04	ALOGPS
logP	7.32	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	9.62	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	158.93 m³·mol⁻¹	ChemAxon
Polarizability	61.05 Å³	ChemAxon
Number of Rings	4	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 4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate (NP0197718)

MOL for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

3D MOL for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

3D SDF for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

3D-SDF for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

PDB for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

3D PDB for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

SMILES for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

INCHI for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

Structure for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)

3D Structure for NP0197718 (4-(benzoyloxy)-2-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]butyl benzoate)