NP-MRD: Showing NP-Card for 3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0166789)

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Record Information

Version

2.0

Created at

2022-09-03 02:13:47 UTC

Updated at

2022-09-03 02:13:47 UTC

NP-MRD ID

NP0166789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

Junipegenin b 7-o-glucoside belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, junipegenin b 7-O-glucoside is considered to be a flavonoid. 3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Juniperus polycarpos. Based on a literature review very few articles have been published on Junipegenin b 7-o-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032204132D          

 36 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652309032204132D          

 36 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0166789

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C1=COC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(OC)C(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O12/c1-31-12-5-4-10(6-13(12)32-2)11-9-34-14-7-15(23(33-3)20(28)17(14)18(11)26)35-24-22(30)21(29)19(27)16(8-25)36-24/h4-7,9,16,19,21-22,24-25,27-30H,8H2,1-3H3/t16-,19-,21+,22-,24-/m1/s1

> <INCHI_KEY>
YBTHHPIEZVFXLZ-YDKVSCPQSA-N

> <FORMULA>
C24H26O12

> <MOLECULAR_WEIGHT>
506.46

> <EXACT_MASS>
506.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.223367743809675

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
0.6393558209999995

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20003163905641

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.857285020696936

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354981798

> <JCHEM_POLAR_SURFACE_AREA>
173.6

> <JCHEM_REFRACTIVITY>
121.23599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   10   31                                                  
CONECT   31   30    7   32                                                  
CONECT   32   31                                                            
CONECT   33    6   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₁₂

Average Mass

506.4600 Da

Monoisotopic Mass

506.14243 Da

IUPAC Name

3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C1=COC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(OC)C(O)=C2C1=O

InChI Identifier

InChI=1S/C24H26O12/c1-31-12-5-4-10(6-13(12)32-2)11-9-34-14-7-15(23(33-3)20(28)17(14)18(11)26)35-24-22(30)21(29)19(27)16(8-25)36-24/h4-7,9,16,19,21-22,24-25,27-30H,8H2,1-3H3/t16-,19-,21+,22-,24-/m1/s1

InChI Key

YBTHHPIEZVFXLZ-YDKVSCPQSA-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
Juniperus polycarpos	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid-7-o-glycoside
Isoflavonoid o-glycoside
3p-methoxyisoflavone
4p-o-methylisoflavone
Hydroxyisoflavonoid
Isoflavone
Phenolic glycoside
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Dimethoxybenzene
1-benzopyran
Benzopyran
O-dimethoxybenzene
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Pyran
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxide
Organic oxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
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	0.69	ALOGPS
logP	0.64	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	173.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.24 m³·mol⁻¹	ChemAxon
Polarizability	50.22 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

C00010149

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

14185734

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0166789)

MOL for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0166789 (3-(3,4-dimethoxyphenyl)-5-hydroxy-6-methoxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)