NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0303286)

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Record Information

Version

2.0

Created at

2022-09-10 17:31:28 UTC

Updated at

2022-09-10 17:31:28 UTC

NP-MRD ID

NP0303286

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

3-[[6-O-[(E)-3-(4-Hydroxyphenyl)propenoyl]-beta-D-glucopyranosyl]oxy]-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenol 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. [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Eucalyptus rubida. Based on a literature review very few articles have been published on 3-[[6-O-[(E)-3-(4-Hydroxyphenyl)propenoyl]-beta-D-glucopyranosyl]oxy]-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102219312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102219312D          

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 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 23 33  2  0  0  0  0
 18 33  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 14 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0303286

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H28O10/c30-20-8-3-17(4-9-20)1-2-19-13-22(32)15-23(14-19)38-29-28(36)27(35)26(34)24(39-29)16-37-25(33)12-7-18-5-10-21(31)11-6-18/h1-15,24,26-32,34-36H,16H2/b2-1+,12-7+/t24-,26-,27+,28-,29-/m1/s1

> <INCHI_KEY>
RYCZLEHSEALCKD-GFRBQNRUSA-N

> <FORMULA>
C29H28O10

> <MOLECULAR_WEIGHT>
536.533

> <EXACT_MASS>
536.168247102

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
54.53265784283832

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
3.8646481893333338

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.064073380539861

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.53783316230124

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491102895687586

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
141.14850000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667 -23.100   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   38                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
CONECT   33   23   18                                                       
CONECT   34   16   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   14   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
3-[[6-O-[(e)-3-(4-Hydroxyphenyl)propenoyl]-b-D-glucopyranosyl]oxy]-5-[(e)-2-(4-hydroxyphenyl)ethenyl]phenol	Generator
3-[[6-O-[(e)-3-(4-Hydroxyphenyl)propenoyl]-β-D-glucopyranosyl]oxy]-5-[(e)-2-(4-hydroxyphenyl)ethenyl]phenol	Generator

Chemical Formula

C₂₉H₂₈O₁₀

Average Mass

536.5330 Da

Monoisotopic Mass

536.16825 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC(O)=CC(\C=C\C3=CC=C(O)C=C3)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C29H28O10/c30-20-8-3-17(4-9-20)1-2-19-13-22(32)15-23(14-19)38-29-28(36)27(35)26(34)24(39-29)16-37-25(33)12-7-18-5-10-21(31)11-6-18/h1-15,24,26-32,34-36H,16H2/b2-1+,12-7+/t24-,26-,27+,28-,29-/m1/s1

InChI Key

RYCZLEHSEALCKD-GFRBQNRUSA-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
Eucalyptus rubida	LOTUS Database	35616633

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
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Phenoxy compound
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Oxane
Monosaccharide
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
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
logP	3.86	ChemAxon
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	141.15 m³·mol⁻¹	ChemAxon
Polarizability	54.53 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

14731037

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0303286)

MOL for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0303286 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)