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Showing NP-Card for 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0247214)

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Record Information
Version1.0
Created at2022-09-07 08:58:24 UTC
Updated at2022-09-07 08:58:24 UTC
NP-MRD IDNP0247214
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
Description8-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Garcinia atroviridis, Garcinia dulcis, Garcinia livingstonei, Garcinia multiflora and Garcinia xanthochymus. 8-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)


  Mrv0541 04121520502D          

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M  END
Download

3D MOL for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

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3D SDF for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

  Mrv0541 04121520502D          

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M  END
> <DATABASE_ID>
NP0247214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2C2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H30O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-11,25,29-30,32-34,36-42,44-45,47-48H,12H2

> <INCHI_KEY>
XUDCXSSDAZIAPT-UHFFFAOYSA-N

> <FORMULA>
C36H30O16

> <MOLECULAR_WEIGHT>
718.62

> <EXACT_MASS>
718.153384886

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
68.83730485851444

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.6737082039999995

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.877886165034707

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.142941457352891

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540666616514946

> <JCHEM_POLAR_SURFACE_AREA>
273.35999999999996

> <JCHEM_REFRACTIVITY>
176.9405

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
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PDB for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  O   UNK     0      -7.150   2.220   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.643   1.900   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.168   0.435   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.661   0.115   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.185  -1.349   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.679  -1.670   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.203  -3.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.234  -4.279   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.758  -5.743   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.788  -6.888   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.251  -6.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.225  -7.528   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.806  -8.673   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.731  -7.848   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.761  -6.704   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.285  -5.239   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.779  -4.919   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.303  -3.454   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.268  -7.024   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.298  -5.880   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.804  -6.200   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.280  -7.664   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.787  -7.985   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       6.250  -8.809   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.726 -10.274   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.744  -8.489   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.216  -2.494   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -3.740  -3.959   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -5.722  -2.174   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -6.753  -3.318   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -6.198  -0.709   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -7.704  -0.389   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   51                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   47                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   39                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17    7   19                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22   30                                                  
CONECT   30   29   19   31                                                  
CONECT   31   30                                                            
CONECT   32   20   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
CONECT   39   15   40   46                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   39                                                       
CONECT   47    5   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49    3   52                                                  
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  116    0
END

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3D PDB for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
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SMILES for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
OCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2C2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O
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INCHI for NP0247214 (8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)
InChI=1S/C36H30O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-11,25,29-30,32-34,36-42,44-45,47-48H,12H2
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SynonymsNot Available
Chemical FormulaC36H30O16
Average Mass718.6200 Da
Monoisotopic Mass718.15338 Da
IUPAC Name8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2=CC(O)=C3C(=O)C=C(OC3=C2C2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C36H30O16/c37-12-25-30(45)32(47)33(48)36(52-25)51-24-11-21(44)26-20(43)10-22(14-3-6-17(40)18(41)7-14)49-35(26)28(24)29-31(46)27-19(42)8-16(39)9-23(27)50-34(29)13-1-4-15(38)5-2-13/h1-11,25,29-30,32-34,36-42,44-45,47-48H,12H2
InChI KeyXUDCXSSDAZIAPT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Garcinia atroviridisLOTUS Database
Garcinia dulcisLOTUS Database
Garcinia livingstoneiLOTUS Database
Garcinia multifloraLOTUS Database
Garcinia xanthochymusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassBiflavonoids and polyflavonoids  
Direct ParentBiflavonoids and polyflavonoids  
Alternative Parents
Substituents
  • Bi- and polyflavonoid skeleton
    • 

  • Stilbene glycoside
    • 

  • Flavonoid-7-o-glycoside
    • 

  • Flavonoid o-glycoside
    • 

  • Pyranoisoflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Flavanone
    • 

  • Isoflavanone
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • Hydroxyisoflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Isoflavonoid skeleton
    • 

  • Isoflavan
    • 

  • Flavan
    • 

  • Isoflavonoid
    • 

  • Phenolic glycoside
    • 

  • Stilbene
    • 

  • Hexose monosaccharide
    • 

  • Chromone
    • 

  • O-glycosyl compound
    • 

  • Glycosyl compound
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Chromane
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Catechol
    • 

  • Pyranone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Acetal
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • 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
logP2.91ALOGPS
logP2.67ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.14ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area273.36 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity176.94 m³·mol⁻¹ChemAxon
Polarizability68.84 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73157060  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]