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Showing NP-Card for 7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0245973)

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Record Information
Version2.0
Created at2022-09-07 07:15:49 UTC
Updated at2022-09-07 07:15:49 UTC
NP-MRD IDNP0245973
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
DescriptionToringin belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Toringin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Toringin has been detected, but not quantified in, fruits and malus (crab apple). 7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Malus doumeri and Pyracantha coccinea. This could make toringin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)


  Mrv0541 05061309142D          

 30 33  0  0  0  0            999 V2000
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    0.0000    3.3000    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
    0.7145    2.0625    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
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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    2.0625    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22  9  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  2  0  0  0  0
 25 18  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
 28 14  1  0  0  0  0
 29 15  1  0  0  0  0
 29 21  1  0  0  0  0
 30 16  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
Download

3D MOL for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Download
3D SDF for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

  Mrv0541 05061309142D          

 30 33  0  0  0  0            999 V2000
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    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
    0.0000    3.3000    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
    0.7145    2.0625    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
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   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    2.0625    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 14  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22  9  1  0  0  0  0
 23 11  1  0  0  0  0
 24 12  2  0  0  0  0
 25 18  1  0  0  0  0
 26 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
 28 14  1  0  0  0  0
 29 15  1  0  0  0  0
 29 21  1  0  0  0  0
 30 16  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC(O)=CC3=C2C(=O)C=C(O3)C2=CC=CC=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O9/c22-9-16-18(25)19(26)20(27)21(30-16)29-15-7-11(23)6-14-17(15)12(24)8-13(28-14)10-4-2-1-3-5-10/h1-8,16,18-23,25-27H,9H2

> <INCHI_KEY>
IRHAYEHCEVRWSB-UHFFFAOYSA-N

> <FORMULA>
C21H20O9

> <MOLECULAR_WEIGHT>
416.3781

> <EXACT_MASS>
416.110732238

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
41.1626347361286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
0.09218636200000002

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.199989115262847

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5286682905033695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463095067

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
103.0774

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
Download
PDB for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
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      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6   11   14                                                       
CONECT    7   11   15                                                       
CONECT    8   12   13                                                       
CONECT    9   16   22                                                       
CONECT   10    4    5   13                                                  
CONECT   11    6    7   23                                                  
CONECT   12    8   17   24                                                  
CONECT   13    8   10   28                                                  
CONECT   14    6   17   28                                                  
CONECT   15    7   17   29                                                  
CONECT   16    9   18   30                                                  
CONECT   17   12   14   15                                                  
CONECT   18   16   19   25                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   29   30                                                  
CONECT   22    9                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   13   14                                                       
CONECT   29   15   21                                                       
CONECT   30   16   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

Download
3D PDB for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
Download
SMILES for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
OCC1OC(OC2=CC(O)=CC3=C2C(=O)C=C(O3)C2=CC=CC=C2)C(O)C(O)C1O
Download
INCHI for NP0245973 (7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
InChI=1S/C21H20O9/c22-9-16-18(25)19(26)20(27)21(30-16)29-15-7-11(23)6-14-17(15)12(24)8-13(28-14)10-4-2-1-3-5-10/h1-8,16,18-23,25-27H,9H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H20O9
Average Mass416.3781 Da
Monoisotopic Mass416.11073 Da
IUPAC Name7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name7-hydroxy-2-phenyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2=CC(O)=CC3=C2C(=O)C=C(O3)C2=CC=CC=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C21H20O9/c22-9-16-18(25)19(26)20(27)21(30-16)29-15-7-11(23)6-14-17(15)12(24)8-13(28-14)10-4-2-1-3-5-10/h1-8,16,18-23,25-27H,9H2
InChI KeyIRHAYEHCEVRWSB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Malus doumeriLOTUS Database
Pyracantha coccineaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid O-glycosides  
Alternative Parents
Substituents
  • Flavonoid-5-o-glycoside
    • 

  • Flavonoid o-glycoside
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Phenolic glycoside
    • 

  • Hexose monosaccharide
    • 

  • Chromone
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Monosaccharide
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Vinylogous ester
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Primary 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
logP0.65ALOGPS
logP0.092ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.53ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.08 m³·mol⁻¹ChemAxon
Polarizability41.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036618  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015534  
KNApSAcK IDC00004109  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74977424  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]