NP-MRD: Showing NP-Card for 1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone (NP0242087)

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Record Information

Version

2.0

Created at

2022-09-07 02:18:39 UTC

Updated at

2022-09-07 02:18:39 UTC

NP-MRD ID

NP0242087

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

Description

1-(4-{[(1R,2S)-1,3-dihydroxy-1-(3-methoxy-4-{[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethan-1-one belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. 1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone is found in Echinacea purpurea. Based on a literature review very few articles have been published on 1-(4-{[(1R,2S)-1,3-dihydroxy-1-(3-methoxy-4-{[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204182D          

 39 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072204182D          

 39 41  0  0  1  0            999 V2000
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    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  6  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 29 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0242087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]1O)[C@@H](O)[C@H](CO)OC1=C(OC)C=C(C=C1OC)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O13/c1-12(29)14-8-17(35-3)25(18(9-14)36-4)37-19(10-27)21(30)13-5-6-15(16(7-13)34-2)38-26-24(33)23(32)22(31)20(11-28)39-26/h5-9,19-24,26-28,30-33H,10-11H2,1-4H3/t19-,20+,21+,22+,23+,24-,26+/m0/s1

> <INCHI_KEY>
GEIZNIKJJFLIOO-RPZJJRIRSA-N

> <FORMULA>
C26H34O13

> <MOLECULAR_WEIGHT>
554.545

> <EXACT_MASS>
554.199941155

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.390696620294605

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-{[(1R,2S)-1,3-dihydroxy-1-(3-methoxy-4-{[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethan-1-one

> <JCHEM_LOGP>
-1.207621909666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.980465743271033

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.167563037889577

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999998

> <JCHEM_REFRACTIVITY>
132.97650000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-{[(1R,2S)-1,3-dihydroxy-1-(3-methoxy-4-{[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

> <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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   12   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    5   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    3   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   38                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   29   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₃

Average Mass

554.5450 Da

Monoisotopic Mass

554.19994 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]1O)[C@@H](O)[C@H](CO)OC1=C(OC)C=C(C=C1OC)C(C)=O

InChI Identifier

InChI=1S/C26H34O13/c1-12(29)14-8-17(35-3)25(18(9-14)36-4)37-19(10-27)21(30)13-5-6-15(16(7-13)34-2)38-26-24(33)23(32)22(31)20(11-28)39-26/h5-9,19-24,26-28,30-33H,10-11H2,1-4H3/t19-,20+,21+,22+,23+,24-,26+/m0/s1

InChI Key

GEIZNIKJJFLIOO-RPZJJRIRSA-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
Echinacea purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Phenolic glycoside
Alkyl-phenylketone
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Dimethoxybenzene
M-dimethoxybenzene
Phenylketone
Acetophenone
Anisole
Benzoyl
Phenoxy compound
Methoxybenzene
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Ketone
Secondary alcohol
Acetal
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Primary alcohol
Alcohol
Organic oxygen compound
Aromatic alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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

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

163081082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone (NP0242087)

MOL for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

3D MOL for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

3D SDF for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

3D-SDF for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

PDB for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

3D PDB for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

SMILES for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

INCHI for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

Structure for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)

3D Structure for NP0242087 (1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone)