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Showing NP-Card for 6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone (NP0049259)

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Record Information
Version2.0
Created at2022-03-17 21:09:36 UTC
Updated at2022-03-17 21:09:36 UTC
NP-MRD IDNP0049259
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone
Description6-C-Fucosylluteolin 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-C-Fucosylluteolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-C-Fucosylluteolin has been detected, but not quantified in, fruits and passion fruits. 6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone is found in Eremochloa ophiuroides. This could make 6-C-fucosylluteolin a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)


  Mrv0541 05061311262D          

 31 34  0  0  0  0            999 V2000
    5.0013    2.0625    0.0000 C   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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   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
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  5  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 22  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  2  0  0  0  0
 25 12  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30  7  1  0  0  0  0
 30 21  1  0  0  0  0
 31 13  1  0  0  0  0
 31 14  1  0  0  0  0
M  END
Download

3D MOL for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)

Download
3D SDF for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)

  Mrv0541 05061311262D          

 31 34  0  0  0  0            999 V2000
    5.0013    2.0625    0.0000 C   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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   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
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  5  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 22  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  2  0  0  0  0
 25 12  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30  7  1  0  0  0  0
 30 21  1  0  0  0  0
 31 13  1  0  0  0  0
 31 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O10/c1-7-17(26)19(28)20(29)21(30-7)16-12(25)6-14-15(18(16)27)11(24)5-13(31-14)8-2-3-9(22)10(23)4-8/h2-7,17,19-23,25-29H,1H3

> <INCHI_KEY>
ROQHTXBYBLROKW-UHFFFAOYSA-N

> <FORMULA>
C21H20O10

> <MOLECULAR_WEIGHT>
432.3775

> <EXACT_MASS>
432.10564686

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
42.61425068461187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3,4,5-trihydroxy-6-methyloxan-2-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
0.692712873666667

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.489548156917554

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.196627616525169

> <JCHEM_PKA_STRONGEST_BASIC>
-3.608542600863829

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
106.46939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3,4,5-trihydroxy-6-methyloxan-2-yl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)
Download
PDB for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   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  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    8   10                                                       
CONECT    5   11   13                                                       
CONECT    6   12   14                                                       
CONECT    7    1   17   30                                                  
CONECT    8    2    4   13                                                  
CONECT    9    3   10   22                                                  
CONECT   10    4    9   23                                                  
CONECT   11    5   15   24                                                  
CONECT   12    6   16   25                                                  
CONECT   13    5    8   31                                                  
CONECT   14    6   15   31                                                  
CONECT   15   11   14   18                                                  
CONECT   16   12   18   21                                                  
CONECT   17    7   19   26                                                  
CONECT   18   15   16   27                                                  
CONECT   19   17   20   28                                                  
CONECT   20   19   21   29                                                  
CONECT   21   16   20   30                                                  
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30    7   21                                                       
CONECT   31   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)
Download
SMILES for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)
CC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O
Download
INCHI for NP0049259 (6-C-(6-Deoxyglucopyranosyl)-3',4',5,7-tetrahydroxyflavone)
InChI=1S/C21H20O10/c1-7-17(26)19(28)20(29)21(30-7)16-12(25)6-14-15(18(16)27)11(24)5-13(31-14)8-2-3-9(22)10(23)4-8/h2-7,17,19-23,25-29H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H20O10
Average Mass432.3775 Da
Monoisotopic Mass432.10565 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3,4,5-trihydroxy-6-methyloxan-2-yl)-4H-chromen-4-one
Traditional Name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3,4,5-trihydroxy-6-methyloxan-2-yl)chromen-4-one
CAS Registry Number132368-05-9
SMILES
CC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O
InChI Identifier
InChI=1S/C21H20O10/c1-7-17(26)19(28)20(29)21(30-7)16-12(25)6-14-15(18(16)27)11(24)5-13(31-14)8-2-3-9(22)10(23)4-8/h2-7,17,19-23,25-29H,1H3
InChI KeyROQHTXBYBLROKW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eremochloa ophiuroidesLOTUS Database
Passiflora edulisFooDB
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid C-glycosides  
Alternative Parents
Substituents
  • Flavonoid c-glycoside
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Phenolic glycoside
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Catechol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Oxane
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Dialkyl ether
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.12ALOGPS
logP0.69ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area177.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.47 m³·mol⁻¹ChemAxon
Polarizability42.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038898  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019512  
KNApSAcK IDC00006106  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74977561  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available