NP-MRD: Showing NP-Card for 5,7-Dimethoxyflavone (NP0050608)

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Record Information

Version

2.0

Created at

2022-04-27 21:58:55 UTC

Updated at

2022-04-27 21:58:55 UTC

NP-MRD ID

NP0050608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dimethoxyflavone

Description

5,7-Dimethoxyflavone, also known as chrysin dimethyl ether or chrysin dme, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 5,7-dimethoxyflavone is considered to be a flavonoid lipid molecule. A dimethoxyflavone that is the 5,7-dimethyl ether derivative of chrysin. 5,7-Dimethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5,7-Dimethoxyflavone has been detected, but not quantified in, tea. 5,7-Dimethoxyflavone is found in Boesenbergia pandurata , Boesenbergia rotunda, Bombax anceps, Caesalpinia pulcherrima , Celosia cristata, Helichrysum herbaceum, Helichrysum nitens, Kaempferia parviflora , Leptospermum scoparium , Melodorum fruticosum, Muntingia calabura, Piper cubeba and Piper porphyrophyllum. This could make 5,7-dimethoxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309142D          

 21 23  0  0  0  0            999 V2000
    0.0000    0.0000    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
    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
    1.4289    0.8250    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
    4.2868    0.8250    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
    2.1434    1.2375    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
    2.8579    0.8250    0.0000 C   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   -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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17 13  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 20  2  1  0  0  0  0
 20 15  1  0  0  0  0
 21 14  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-10H,1-2H3

> <INCHI_KEY>
JRFZSUMZAUHNSL-UHFFFAOYSA-N

> <FORMULA>
C17H14O4

> <MOLECULAR_WEIGHT>
282.2907

> <EXACT_MASS>
282.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.855526253217707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.652042567333333

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.364721570861334

> <JCHEM_PKA_STRONGEST_BASIC>
-4.514411431675101

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
79.8976

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dimethoxyflavone

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -2.310   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   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       8.002   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       5.335   0.000   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  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   12   15                                                       
CONECT    9   12   16                                                       
CONECT   10   13   14                                                       
CONECT   11    6    7   14                                                  
CONECT   12    8    9   19                                                  
CONECT   13   10   17   18                                                  
CONECT   14   10   11   21                                                  
CONECT   15    8   17   20                                                  
CONECT   16    9   17   21                                                  
CONECT   17   13   15   16                                                  
CONECT   18   13                                                            
CONECT   19    1   12                                                       
CONECT   20    2   15                                                       
CONECT   21   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
Chrysin dimethyl ether	ChEBI
Chrysin 5,7-dimethyl ether	Kegg
5,7-Dimethoxy-2-phenyl-4H-1-benzopyran-4-one	HMDB
5,7-Dimethoxy-flavone	HMDB
Chrysin dimethylether	HMDB
Chrysin dme	HMDB
Dimethylchrysin	HMDB
5,7-Dimethoxyflavone	ChEBI

Chemical Formula

C₁₇H₁₄O₄

Average Mass

282.2907 Da

Monoisotopic Mass

282.08921 Da

IUPAC Name

5,7-dimethoxy-2-phenyl-4H-chromen-4-one

Traditional Name

5,7-dimethoxyflavone

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H14O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-10H,1-2H3

InChI Key

JRFZSUMZAUHNSL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boesenbergia pandurata	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633
Bombax anceps	LOTUS Database	35616633
Caesalpinia pulcherrima	Plant	KNApSAcK
Celosia cristata	LOTUS Database	35616633
Helichrysum herbaceum	Plant	KNApSAcK
Helichrysum nitens	Plant	KNApSAcK
Kaempferia parviflora	Plant	KNApSAcK
Leptospermum scoparium	Plant	KNApSAcK
Melodorum fruticosum	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Piper cubeba	LOTUS Database	35616633
Piper porphyrophyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous ester
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dimethoxyflavone (CHEBI:3684 )
flavones (C10029 )
Flavones and Flavonols (C10029 )
Flavones and Flavonols (LMPK12110188 )

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	3.29	ALOGPS
logP	2.65	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.36	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	29.86 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