NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0185906)

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Record Information

Version

2.0

Created at

2022-09-04 01:31:42 UTC

Updated at

2022-09-04 01:31:42 UTC

NP-MRD ID

NP0185906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosiduronic acid belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. (2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Spinacia oleracea. Based on a literature review very few articles have been published on 5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosiduronic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042203312D          

 38 41  0  0  1  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042203312D          

 38 41  0  0  1  0            999 V2000
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 33 34  1  1  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C(=O)C2=C(O)C(O)=C(OC)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O14/c1-33-9-5-4-8(6-10(9)34-2)20-21(37-24-19(30)17(28)18(29)22(38-24)23(31)32)16(27)13-11(36-20)7-12(35-3)14(25)15(13)26/h4-7,17-19,22,24-26,28-30H,1-3H3,(H,31,32)/t17-,18-,19+,22-,24+/m0/s1

> <INCHI_KEY>
LURNGPWLQCDCBE-YPQORGHUSA-N

> <FORMULA>
C24H24O14

> <MOLECULAR_WEIGHT>
536.442

> <EXACT_MASS>
536.116605453

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.720056756060195

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_LOGP>
0.309556088333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.385330900178099

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.587338705004305

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868297480421157

> <JCHEM_POLAR_SURFACE_AREA>
210.89999999999995

> <JCHEM_REFRACTIVITY>
124.57069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667   1.540   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   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+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       8.002   1.540   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    7   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   23   34                                                  
CONECT   34   33                                                            
CONECT   35    6   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl b-D-glucopyranosiduronate	Generator
5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl b-D-glucopyranosiduronic acid	Generator
5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosiduronate	Generator
5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl β-D-glucopyranosiduronate	Generator
5,6-Dihydroxy-2-(3,4-dimethoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl β-D-glucopyranosiduronic acid	Generator

Chemical Formula

C₂₄H₂₄O₁₄

Average Mass

536.4420 Da

Monoisotopic Mass

536.11661 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C(=O)C2=C(O)C(O)=C(OC)C=C2O1

InChI Identifier

InChI=1S/C24H24O14/c1-33-9-5-4-8(6-10(9)34-2)20-21(37-24-19(30)17(28)18(29)22(38-24)23(31)32)16(27)13-11(36-20)7-12(35-3)14(25)15(13)26/h4-7,17-19,22,24-26,28-30H,1-3H3,(H,31,32)/t17-,18-,19+,22-,24+/m0/s1

InChI Key

LURNGPWLQCDCBE-YPQORGHUSA-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
Spinacia oleracea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glucuronides

Alternative Parents

Substituents

Flavonoid-3-o-glucuronide
Flavonoid-3-o-glycoside
7-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
3p-methoxyflavonoid-skeleton
6-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
Flavone
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
O-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Beta-hydroxy acid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Oxacycle
Polyol
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
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	0.31	ChemAxon
pKa (Strongest Acidic)	2.59	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	210.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.57 m³·mol⁻¹	ChemAxon
Polarizability	50.72 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

9181201

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11006011

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0185906)

MOL for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0185906 ((2s,3s,4s,5r,6s)-6-{[2-(3,4-dimethoxyphenyl)-5,6-dihydroxy-7-methoxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)