NP-MRD: Showing NP-Card for (2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate (NP0242475)

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Record Information

Version

2.0

Created at

2022-09-07 02:47:58 UTC

Updated at

2022-09-07 02:47:58 UTC

NP-MRD ID

NP0242475

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate

Description

(2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. (2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate is found in Gymnanthemum myrianthum. Based on a literature review very few articles have been published on (2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204472D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072204472D          

 38 39  0  0  1  0            999 V2000
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    6.1824  -10.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8711   -9.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432  -10.3441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7237  -10.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3793   -8.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0681   -4.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -4.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9041   -3.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -2.6788    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  1  0  0  0  0
  7  6  1  1  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  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  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
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 26 34  1  0  0  0  0
  5 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242475

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@H](COC(=O)CC(C)C)[C@H](COC(=O)CC(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O8/c1-19(2)11-29(33)37-17-23(13-21-7-9-25(31)27(15-21)35-5)24(18-38-30(34)12-20(3)4)14-22-8-10-26(32)28(16-22)36-6/h7-10,15-16,19-20,23-24,31-32H,11-14,17-18H2,1-6H3/t23-,24+

> <INCHI_KEY>
LCNKELFTVLGXKF-PSWAGMNNSA-N

> <FORMULA>
C30H42O8

> <MOLECULAR_WEIGHT>
530.658

> <EXACT_MASS>
530.287968312

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
58.40782285782013

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate

> <JCHEM_LOGP>
6.079359119999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.246955924084146

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.644895932756185

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5879813125514355

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
145.14299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.645  -3.411   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.563  -4.647   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.951  -6.060   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.869  -7.297   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.257  -8.710   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.175  -9.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.563 -11.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.033 -11.536   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.115 -10.300   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.585 -10.477   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.973 -11.890   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.138  -9.417   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.526 -10.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.220  -8.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.481 -12.596   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.011 -12.420   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.622 -11.007   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.152 -10.830   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.070 -12.066   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.764  -9.417   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.294  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.906  -7.827   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.212 -10.477   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.869 -14.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.787 -15.246   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.317 -15.069   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.234 -16.306   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.622 -17.719   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.540 -18.956   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.093 -17.896   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.481 -19.309   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.951 -19.486   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.175 -16.659   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.727  -8.887   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.809  -7.650   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.421  -6.237   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.503  -5.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   26                                                       
CONECT   35    5   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoic acid	Generator

Chemical Formula

C₃₀H₄₂O₈

Average Mass

530.6580 Da

Monoisotopic Mass

530.28797 Da

IUPAC Name

(2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate

Traditional Name

(2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@H](COC(=O)CC(C)C)[C@H](COC(=O)CC(C)C)CC2=CC=C(O)C(OC)=C2)=CC=C1O

InChI Identifier

InChI=1S/C30H42O8/c1-19(2)11-29(33)37-17-23(13-21-7-9-25(31)27(15-21)35-5)24(18-38-30(34)12-20(3)4)14-22-8-10-26(32)28(16-22)36-6/h7-10,15-16,19-20,23-24,31-32H,11-14,17-18H2,1-6H3/t23-,24+

InChI Key

LCNKELFTVLGXKF-PSWAGMNNSA-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
Gymnanthemum myrianthum	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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Carboxylic acid ester
Carboxylic acid derivative
Ether
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	6.08	ChemAxon
pKa (Strongest Acidic)	9.64	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	17	ChemAxon
Refractivity	145.14 m³·mol⁻¹	ChemAxon
Polarizability	58.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162848382

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate (NP0242475)

MOL for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

3D MOL for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

3D SDF for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

3D-SDF for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

PDB for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

3D PDB for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

SMILES for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

INCHI for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

Structure for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)

3D Structure for NP0242475 ((2s,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methylbutanoyl)oxy]butyl 3-methylbutanoate)