NP-MRD: Showing NP-Card for 4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one (NP0284196)

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Record Information

Version

2.0

Created at

2022-09-09 11:47:52 UTC

Updated at

2022-09-09 11:47:52 UTC

NP-MRD ID

NP0284196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one

Description

4,7-Dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]-2H-chromen-2-one 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. 4,7-Dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201501252D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201501252D          

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M  END
> <DATABASE_ID>
NP0284196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC2=CC=C(OC3OC(CO)C(O)C(O)C3O)C=C2)=C2C(OC(=O)C(C)=C2OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O10/c1-13-24(33-3)20-15(10-17(32-2)11-18(20)35-25(13)31)7-4-14-5-8-16(9-6-14)34-26-23(30)22(29)21(28)19(12-27)36-26/h4-11,19,21-23,26-30H,12H2,1-3H3

> <INCHI_KEY>
ZXUJUHSPUYLMNR-UHFFFAOYSA-N

> <FORMULA>
C26H28O10

> <MOLECULAR_WEIGHT>
500.5

> <EXACT_MASS>
500.168247102

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.57734026388097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]-2H-chromen-2-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.1487269496666666

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196091452687789

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20014177203259

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343686506

> <JCHEM_POLAR_SURFACE_AREA>
144.14000000000001

> <JCHEM_REFRACTIVITY>
128.5925

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   36                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
CONECT   34   21   35                                                       
CONECT   35   34   18                                                       
CONECT   36   15    3    9                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₀

Average Mass

500.5000 Da

Monoisotopic Mass

500.16825 Da

IUPAC Name

4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]-2H-chromen-2-one

Traditional Name

4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC2=CC=C(OC3OC(CO)C(O)C(O)C3O)C=C2)=C2C(OC(=O)C(C)=C2OC)=C1

InChI Identifier

InChI=1S/C26H28O10/c1-13-24(33-3)20-15(10-17(32-2)11-18(20)35-25(13)31)7-4-14-5-8-16(9-6-14)34-26-23(30)22(29)21(28)19(12-27)36-26/h4-11,19,21-23,26-30H,12H2,1-3H3

InChI Key

ZXUJUHSPUYLMNR-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
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumarin
1-benzopyran
Benzopyran
Styrene
Anisole
Phenol ether
Phenoxy compound
Pyranone
Alkyl aryl ether
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Pyran
Oxane
Vinylogous ester
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.89	ALOGPS
logP	1.15	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	144.14 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	128.59 m³·mol⁻¹	ChemAxon
Polarizability	51.58 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 4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one (NP0284196)

MOL for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

3D MOL for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

3D SDF for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

3D-SDF for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

PDB for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

3D PDB for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

SMILES for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

INCHI for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

Structure for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)

3D Structure for NP0284196 (4,7-dimethoxy-3-methyl-5-[2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethenyl]chromen-2-one)