NP-MRD: Showing NP-Card for 6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one (NP0257593)

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Record Information

Version

2.0

Created at

2022-09-07 22:45:44 UTC

Updated at

2022-09-07 22:45:44 UTC

NP-MRD ID

NP0257593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

Description

6-[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one is found in Gentiana verna. Based on a literature review very few articles have been published on 6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200452D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082200452D          

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    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 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
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  0  0  0  0
 18 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
  2 43  1  0  0  0  0
 14 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(OCC2OC(O)C(O)C(O)C2O)C(O)C1O)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O16/c28-6-15-19(33)23(37)26(40-7-16-20(34)22(36)24(38)27(39)43-16)25(42-15)18-12(32)5-14-17(21(18)35)11(31)4-13(41-14)8-1-2-9(29)10(30)3-8/h1-5,15-16,19-20,22-30,32-39H,6-7H2

> <INCHI_KEY>
WCSZXEBGDNWSQK-UHFFFAOYSA-N

> <FORMULA>
C27H30O16

> <MOLECULAR_WEIGHT>
610.521

> <EXACT_MASS>
610.153384886

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
58.65538068917474

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one

> <JCHEM_LOGP>
-2.1250327386666674

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.710193961299467

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.137510905868737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6534240949677077

> <JCHEM_POLAR_SURFACE_AREA>
276.52

> <JCHEM_REFRACTIVITY>
140.42640000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   43                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    4   14                                                       
CONECT   14   13   15   43                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   41                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   31   40                                                  
CONECT   40   39                                                            
CONECT   41   18   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    2   14                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₆

Average Mass

610.5210 Da

Monoisotopic Mass

610.15338 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OCC1OC(C(OCC2OC(O)C(O)C(O)C2O)C(O)C1O)C1=C(O)C=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H30O16/c28-6-15-19(33)23(37)26(40-7-16-20(34)22(36)24(38)27(39)43-16)25(42-15)18-12(32)5-14-17(21(18)35)11(31)4-13(41-14)8-1-2-9(29)10(30)3-8/h1-5,15-16,19-20,22-30,32-39H,6-7H2

InChI Key

WCSZXEBGDNWSQK-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

Species Name	Source	Reference
Gentiana verna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
Flavone
5-hydroxyflavonoid
7-hydroxyflavonoid
Phenolic glycoside
C-glycosyl compound
Chromone
Glycosyl compound
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Hemiacetal
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
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

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

162952089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one (NP0257593)

MOL for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

3D MOL for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

3D SDF for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

3D-SDF for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

PDB for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

3D PDB for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

SMILES for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

INCHI for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

Structure for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)

3D Structure for NP0257593 (6-[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5,6-tetrahydroxyoxan-2-yl)methoxy]oxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one)