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Showing NP-Card for 5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone (NP0335297)

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Record Information
Version2.0
Created at2024-09-11 00:57:15 UTC
Updated at2024-09-11 00:57:15 UTC
NP-MRD IDNP0335297
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone
Description5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. 5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone has been detected, but not quantified in, citrus. This could make 5-hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)


  Mrv0541 05061312312D          

 29 32  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   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    2.0625    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    2.0625    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
    4.8419    1.6500    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   -0.4125    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
   -1.4289    0.8250    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    0.0000    0.8250    0.0000 C   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
    2.1434   -0.4125    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
    2.8579    3.3000    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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    2.3174    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
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 11  2  0  0  0  0
 18 13  1  0  0  0  0
 19 12  2  0  0  0  0
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 20 19  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23 10  1  0  0  0  0
 24  2  1  0  0  0  0
 24 11  1  0  0  0  0
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 25 12  1  0  0  0  0
 26  4  1  0  0  0  0
 26 19  1  0  0  0  0
 27  8  1  0  0  0  0
 27 13  1  0  0  0  0
 28  8  1  0  0  0  0
 28 18  1  0  0  0  0
 29 17  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
Download

3D MOL for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)

Download
3D SDF for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)

  Mrv0541 05061312312D          

 29 32  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   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    2.0625    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    2.0625    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
    4.8419    1.6500    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   -0.4125    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
   -1.4289    0.8250    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    0.0000    0.8250    0.0000 C   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
    2.1434   -0.4125    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
    2.8579    3.3000    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
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570    2.3174    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
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  2  0  0  0  0
 14 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 11  2  0  0  0  0
 18 13  1  0  0  0  0
 19 12  2  0  0  0  0
 20 14  2  0  0  0  0
 20 19  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23 10  1  0  0  0  0
 24  2  1  0  0  0  0
 24 11  1  0  0  0  0
 25  3  1  0  0  0  0
 25 12  1  0  0  0  0
 26  4  1  0  0  0  0
 26 19  1  0  0  0  0
 27  8  1  0  0  0  0
 27 13  1  0  0  0  0
 28  8  1  0  0  0  0
 28 18  1  0  0  0  0
 29 17  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(OC)C=C2OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O9/c1-23-10-7-12(25-3)19(26-4)20-14(10)15(21)16(22)17(29-20)9-5-11(24-2)18-13(6-9)27-8-28-18/h5-7,22H,8H2,1-4H3

> <INCHI_KEY>
ADHJMNNFIWLSBG-UHFFFAOYSA-N

> <FORMULA>
C20H18O9

> <MOLECULAR_WEIGHT>
402.3515

> <EXACT_MASS>
402.095082174

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
39.913437146816044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-5,7,8-trimethoxy-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.7131091556666675

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50119588388636

> <JCHEM_PKA_STRONGEST_BASIC>
-4.009836920440333

> <JCHEM_POLAR_SURFACE_AREA>
101.91000000000003

> <JCHEM_REFRACTIVITY>
100.55829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5,7,8-trimethoxy-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)
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PDB for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)
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      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   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       9.038   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   3.850   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.001   2.310   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       8.133   1.834   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.133   4.326   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5    9   11                                                       
CONECT    6    9   13                                                       
CONECT    7   10   12                                                       
CONECT    8   27   28                                                       
CONECT    9    5    6   17                                                  
CONECT   10    7   14   23                                                  
CONECT   11    5   18   24                                                  
CONECT   12    7   19   25                                                  
CONECT   13    6   18   27                                                  
CONECT   14   10   15   20                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   22                                                  
CONECT   17    9   16   29                                                  
CONECT   18   11   13   28                                                  
CONECT   19   12   20   26                                                  
CONECT   20   14   19   29                                                  
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    1   10                                                       
CONECT   24    2   11                                                       
CONECT   25    3   12                                                       
CONECT   26    4   19                                                       
CONECT   27    8   13                                                       
CONECT   28    8   18                                                       
CONECT   29   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

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3D PDB for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)
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SMILES for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)
COC1=C2OCOC2=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(OC)C=C2OC
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INCHI for NP0335297 (5-Hydroxy-3,3',7,8-tetramethoxy-4',5'-methylenedioxyflavone)
InChI=1S/C20H18O9/c1-23-10-7-12(25-3)19(26-4)20-14(10)15(21)16(22)17(29-20)9-5-11(24-2)18-13(6-9)27-8-28-18/h5-7,22H,8H2,1-4H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H18O9
Average Mass402.3515 Da
Monoisotopic Mass402.09508 Da
IUPAC Name3-hydroxy-5,7,8-trimethoxy-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-4H-chromen-4-one
Traditional Name3-hydroxy-5,7,8-trimethoxy-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)chromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=C2OCOC2=CC(=C1)C1=C(O)C(=O)C2=C(O1)C(OC)=C(OC)C=C2OC
InChI Identifier
InChI=1S/C20H18O9/c1-23-10-7-12(25-3)19(26-4)20-14(10)15(21)16(22)17(29-20)9-5-11(24-2)18-13(6-9)27-8-28-18/h5-7,22H,8H2,1-4H3
InChI KeyADHJMNNFIWLSBG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavones  
Direct ParentFlavonols  
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
    • 

  • 5-methoxyflavonoid-skeleton
    • 

  • 7-methoxyflavonoid-skeleton
    • 

  • 8-methoxyflavonoid-skeleton
    • 

  • 3-hydroxyflavone
    • 

  • 3-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzodioxole
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Vinylogous ester
    • 

  • Heteroaromatic compound
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP1.59ALOGPS
logP1.71ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area101.91 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.56 m³·mol⁻¹ChemAxon
Polarizability39.91 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0041257  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021165  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131753088  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available