NP-MRD: Showing NP-Card for (5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate (NP0220996)

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Record Information

Version

2.0

Created at

2022-09-05 22:27:24 UTC

Updated at

2022-09-05 22:27:24 UTC

NP-MRD ID

NP0220996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate

Description

(5-Hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate 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 (5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161504072D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161504072D          

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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=C(O)C=C2COC(=O)C2=CC=CC=C2CC(=O)C2=CC=CC=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O10/c29-14-23-24(32)25(33)26(34)28(38-23)37-22-11-10-19(30)12-18(22)15-36-27(35)20-9-5-4-8-17(20)13-21(31)16-6-2-1-3-7-16/h1-12,23-26,28-30,32-34H,13-15H2

> <INCHI_KEY>
VHDJHNGKXWBNIQ-UHFFFAOYSA-N

> <FORMULA>
C28H28O10

> <MOLECULAR_WEIGHT>
524.522

> <EXACT_MASS>
524.168247102

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.96747866584213

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.217984499

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.077667755141746

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.674261036201187

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923448972835

> <JCHEM_POLAR_SURFACE_AREA>
162.98

> <JCHEM_REFRACTIVITY>
133.92680000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334 -19.250   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334 -23.870   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.668 -11.550   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   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33    5   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(5-Hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₀

Average Mass

524.5220 Da

Monoisotopic Mass

524.16825 Da

IUPAC Name

(5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate

Traditional Name

(5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC=C(O)C=C2COC(=O)C2=CC=CC=C2CC(=O)C2=CC=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C28H28O10/c29-14-23-24(32)25(33)26(34)28(38-23)37-22-11-10-19(30)12-18(22)15-36-27(35)20-9-5-4-8-17(20)13-21(31)16-6-2-1-3-7-16/h1-12,23-26,28-30,32-34H,13-15H2

InChI Key

VHDJHNGKXWBNIQ-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

Not Available

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
Alkyl-phenylketone
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Benzoate ester
Benzyloxycarbonyl
Benzoic acid or derivatives
4-alkoxyphenol
Phenylketone
Phenol ether
Benzoyl
Phenoxy compound
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Ketone
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	2.21	ALOGPS
logP	2.22	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	133.93 m³·mol⁻¹	ChemAxon
Polarizability	52.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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 (5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate (NP0220996)

MOL for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

3D MOL for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

3D SDF for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

3D-SDF for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

PDB for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

3D PDB for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

SMILES for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

INCHI for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

Structure for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)

3D Structure for NP0220996 ((5-hydroxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-(2-oxo-2-phenylethyl)benzoate)