NP-MRD: Showing NP-Card for 5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone (NP0335559)

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Record Information

Version

2.0

Created at

2024-09-11 02:09:47 UTC

Updated at

2024-09-11 02:09:48 UTC

NP-MRD ID

NP0335559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone

Description

5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. 5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone has been detected, but not quantified in, citrus. This could make 5,6,7,8-tetrahydroxy-3',4'-dimethoxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310282D          

 25 27  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
   -5.0013    1.2375    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    2.4750    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
   -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
   -3.5724    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
   -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
    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
    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
    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
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    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
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18  8  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23  9  1  0  0  0  0
 24  2  1  0  0  0  0
 24 11  1  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
M  END


  Mrv0541 05061310282D          

 25 27  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
   -5.0013    1.2375    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    2.4750    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
   -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
   -3.5724    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
   -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
    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
    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
    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
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    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
  4  3  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18  8  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 23  1  1  0  0  0  0
 23  9  1  0  0  0  0
 24  2  1  0  0  0  0
 24 11  1  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(O)=C(O)C(O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O8/c1-23-9-4-3-7(5-11(9)24-2)10-6-8(18)12-13(19)14(20)15(21)16(22)17(12)25-10/h3-6,19-22H,1-2H3

> <INCHI_KEY>
WTGSDFJZUGAHBH-UHFFFAOYSA-N

> <FORMULA>
C17H14O8

> <MOLECULAR_WEIGHT>
346.2883

> <EXACT_MASS>
346.068867424

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
33.65782724978237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.0877812806666656

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.042207483405576

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.341152830798085

> <JCHEM_PKA_STRONGEST_BASIC>
-4.537913038485413

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
87.8212

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydroxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -9.336   2.310   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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3    4    7                                                       
CONECT    4    3    9                                                       
CONECT    5    7   11                                                       
CONECT    6    8   10                                                       
CONECT    7    3    5   10                                                  
CONECT    8    6   12   18                                                  
CONECT    9    4   11   23                                                  
CONECT   10    6    7   25                                                  
CONECT   11    5    9   24                                                  
CONECT   12    8   13   17                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   22                                                  
CONECT   17   12   16   25                                                  
CONECT   18    8                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23    1    9                                                       
CONECT   24    2   11                                                       
CONECT   25   10   17                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₄O₈

Average Mass

346.2883 Da

Monoisotopic Mass

346.06887 Da

IUPAC Name

2-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydroxy-4H-chromen-4-one

Traditional Name

2-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydroxychromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(O)=C(O)C(O)=C2O1

InChI Identifier

InChI=1S/C17H14O8/c1-23-9-4-3-7(5-11(9)24-2)10-6-8(18)12-13(19)14(20)15(21)16(22)17(12)25-10/h3-6,19-22H,1-2H3

InChI Key

WTGSDFJZUGAHBH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
5-hydroxyflavonoid
6-hydroxyflavonoid
7-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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
logP	2.69	ALOGPS
logP	2.09	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.34	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.82 m³·mol⁻¹	ChemAxon
Polarizability	33.66 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038466

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017825

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

131752378

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone (NP0335559)

MOL for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

3D MOL for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

3D SDF for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

3D-SDF for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

PDB for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

3D PDB for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

SMILES for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

INCHI for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

Structure for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)

3D Structure for NP0335559 (5,6,7,8-Tetrahydroxy-3',4'-dimethoxyflavone)