NP-MRD: Showing NP-Card for 7-Methoxyflavone (NP0052233)

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Record Information

Version

2.0

Created at

2022-04-27 23:22:07 UTC

Updated at

2022-04-27 23:22:07 UTC

NP-MRD ID

NP0052233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Methoxyflavone

Description

7-Methoxyflavone 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, 7-methoxyflavone is considered to be a flavonoid lipid molecule. 7-Methoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The O-methylated flavonoids or methoxyflavonoids are flavonoids with methylations on hydroxyl groups (methoxy bonds). O-methylation has an effect on the solubility of flavonoids. Those positions can be ortho, meta, para and there can be a special 3-O-methyltransferase for the 3-OH position. Those enzymes mediate the O-methylation on a specific hydroxyl group, like on 4' (example in Catharanthus roseus) or 3' (example in rice) positions. O-methylated flavonoids formation implies the presence of specific O-methyltransferase (OMT) enzymes which accept a variety of substrates. 7-Methoxyflavone is found in Conchocarpus heterophyllus, Muntingia calabura, Pimelea simplex and Salix matsudana. Calamondin orange (Citrus mitis) exhibits all of those activities.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.6337   -0.3462    1.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -0.6392    1.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -0.2126    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5395    0.4710   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5536    0.9021   -1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.6264   -1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223    1.0426   -1.8723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980    1.6564   -2.9219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1077    0.7746   -1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500    0.0964   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -0.2054    0.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7729    0.1742   -0.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0599   -0.1412   -0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3006   -0.8262    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2309   -1.2051    1.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9436   -0.8960    1.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3312   -0.2873    0.4061 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9201   -0.0505    0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -0.4595    0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3760   -0.8886    1.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7493   -0.7504    0.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8370    0.7291    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714    0.6781   -0.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7863    1.4359   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8608    1.1208   -2.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    0.7082   -1.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9212    0.1430   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3138   -1.0626    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4191   -1.7413    2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1325   -1.2091    1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033   -0.9877    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 19  2  0
 19 18  1  0
 18  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 17  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4  3  1  0
 16 11  1  0
 17 18  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 31  1  0
  5 24  1  0
  4 23  1  0
  9 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv1533004241522222D          

 19 21  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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   -1.6500    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
    0.7145   -0.4125    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 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C(=O)C=C(O2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-10H,1H3

> <INCHI_KEY>
QKNDCRMJDZLFEG-UHFFFAOYSA-N

> <FORMULA>
C16H12O3

> <MOLECULAR_WEIGHT>
252.269

> <EXACT_MASS>
252.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.924466058491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-2-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
2.809713832999999

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.818347399493852

> <JCHEM_PKA_STRONGEST_BASIC>
-4.736002017778921

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
73.43440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-2-phenylchromen-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   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       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    5                                                       
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₃

Average Mass

252.2690 Da

Monoisotopic Mass

252.07864 Da

IUPAC Name

7-methoxy-2-phenyl-4H-chromen-4-one

Traditional Name

7-methoxy-2-phenylchromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C(=O)C=C(O2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H12O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-10H,1H3

InChI Key

QKNDCRMJDZLFEG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Conchocarpus heterophyllus	LOTUS Database	35616633
Muntingia calabura	LOTUS Database	35616633
Pimelea simplex	Plant	KNApSAcK
Salix matsudana	Plant	KNApSAcK

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110021 )

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	3.53	ALOGPS
logP	2.81	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.43 m³·mol⁻¹	ChemAxon
Polarizability	26.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

O-methylated flavonoid

METLIN ID

Not Available

PubChem Compound

466268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-Methoxyflavone (NP0052233)

MOL for NP0052233 (7-Methoxyflavone)

3D MOL for NP0052233 (7-Methoxyflavone)

3D SDF for NP0052233 (7-Methoxyflavone)

3D-SDF for NP0052233 (7-Methoxyflavone)

PDB for NP0052233 (7-Methoxyflavone)

3D PDB for NP0052233 (7-Methoxyflavone)

SMILES for NP0052233 (7-Methoxyflavone)

INCHI for NP0052233 (7-Methoxyflavone)

Structure for NP0052233 (7-Methoxyflavone)

3D Structure for NP0052233 (7-Methoxyflavone)