NP-MRD: Showing NP-Card for (E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside (NP0062600)

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Record Information

Version

2.0

Created at

2022-04-28 07:12:57 UTC

Updated at

2022-04-28 07:12:57 UTC

NP-MRD ID

NP0062600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside

Description

(2S,3R,4S,5R,6R)-2-{3-hydroxy-4-[(E)-2-(3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. (E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside is found in Morus alba and Schoenocaulon officinale. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{3-hydroxy-4-[(E)-2-(3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209122D          

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M  END

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M  END


  Mrv1652304282209122D          

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    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 20 22  1  1  0  0  0
 22 23  1  0  0  0  0
 19 24  1  1  0  0  0
 18 25  1  1  0  0  0
 17 26  1  6  0  0  0
 10 27  1  0  0  0  0
  3 28  1  0  0  0  0
 29 28  1  1  0  0  0
 29 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  1  0  0  0  0
 29 34  1  0  0  0  0
 33 35  1  1  0  0  0
 35 36  1  0  0  0  0
 32 37  1  1  0  0  0
 31 38  1  1  0  0  0
 30 39  1  6  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062600

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C(\C=C\C3=CC(O)=CC(O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)=C3)C=C2)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O14/c27-9-17-19(31)21(33)23(35)25(39-17)37-14-4-3-12(16(30)8-14)2-1-11-5-13(29)7-15(6-11)38-26-24(36)22(34)20(32)18(10-28)40-26/h1-8,17-36H,9-10H2/b2-1+/t17-,18-,19+,20+,21+,22+,23-,24-,25-,26-/m1/s1

> <INCHI_KEY>
HPSWAEGGWLOOKT-ZSAPNMPZSA-N

> <FORMULA>
C26H32O14

> <MOLECULAR_WEIGHT>
568.528

> <EXACT_MASS>
568.17920571

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
56.251551244668974

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{3-hydroxy-4-[(E)-2-(3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-1.4373106219999991

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.340866853339858

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.667469242113945

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648395345694367

> <JCHEM_POLAR_SURFACE_AREA>
239.21999999999994

> <JCHEM_REFRACTIVITY>
133.7252

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{3-hydroxy-4-[(E)-2-(3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   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      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0     -14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0     -14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0     -12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   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  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19                                                            
CONECT   25   18                                                            
CONECT   26   17                                                            
CONECT   27   10                                                            
CONECT   28    3   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   39                                                  
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   29                                                       
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37   32                                                            
CONECT   38   31                                                            
CONECT   39   30                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₄

Average Mass

568.5280 Da

Monoisotopic Mass

568.17921 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{3-hydroxy-4-[(E)-2-(3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R,6R)-2-{3-hydroxy-4-[(E)-2-(3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C(\C=C\C3=CC(O)=CC(O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)=C3)C=C2)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H32O14/c27-9-17-19(31)21(33)23(35)25(39-17)37-14-4-3-12(16(30)8-14)2-1-11-5-13(29)7-15(6-11)38-26-24(36)22(34)20(32)18(10-28)40-26/h1-8,17-36H,9-10H2/b2-1+/t17-,18-,19+,20+,21+,22+,23-,24-,25-,26-/m1/s1

InChI Key

HPSWAEGGWLOOKT-ZSAPNMPZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Morus alba	Plant	KNApSAcK
Schoenocaulon officinale	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	-0.7	ALOGPS
logP	-1.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	239.22 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.73 m³·mol⁻¹	ChemAxon
Polarizability	56.25 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

162879292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside (NP0062600)

MOL for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

3D MOL for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

3D SDF for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

3D-SDF for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

PDB for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

3D PDB for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

SMILES for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

INCHI for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

Structure for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)

3D Structure for NP0062600 ((E)-3-[2-[4-(beta-D-Glucopyranosyloxy)-2-hydroxyphenyl]ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside)