NP-MRD: Showing NP-Card for Apigenin 7,4'-dimethyl ether (NP0043838)

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Record Information

Version

1.0

Created at

2021-06-22 17:25:08 UTC

Updated at

2021-08-20 00:00:44 UTC

NP-MRD ID

NP0043838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apigenin 7,4'-dimethyl ether

Description

Apigenin 7,4'-dimethyl ether, also known as 4',7-dimethylapigenin or 4,7-dimethoxy-5-hydroxyflavone, 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, apigenin 7,4'-dimethyl ether is considered to be a flavonoid. Apigenin 7,4'-dimethyl ether is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Apigenin 7,4'-dimethyl ether is found in Aleuritopteris farinosa, Artabotrys hexapetalus, Artemisia pontica, Baccharis tola, Betula pendula, Betula platyphylla, Boesenbergia rotunda, Bombax anceps, Calea jamaicensis, Callicarpa americana, Cota palaestina, Cryptomeria japonica, Currania robertiana, Gymnocarpium robertianum, Hyptis capitata, Leucas cephalotes, Montanoa leucantha, Ocimum basilicum L. , Ophyrosporus charrua, Origanum dictamnus, Oroxylum indicum, Peperomia blanda, Peperomia leptostachya, Platycladus orientalis, Plectranthus fruticosus, Podocarpus fasciculus, Pongamia pinnata, Reboulia hemisphaerica, Salvia bucharica, Salvia hydrangea, Rosmarinus officinalis , Salvia staminea, Sideritis marmorea, Streptomyces avermitilis, Teucrium heterophyllum, Thymus vulgaris, Trocholejeunea sandvicensis, Turnera diffusa, Veratrum dahuricum and Xanthorrhoea australis. It was first documented in 2005 (PMID: 16323541). Based on a literature review very few articles have been published on Apigenin 7,4'-dimethyl ether (PMID: 27719955) (PMID: 30612223).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043838
     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    6.7345    0.9736    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5458    1.7200   -0.0410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2913    1.1191   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    1.8925   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8958    1.3335   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -0.0528    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5995    0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333   -1.9471    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -2.5004    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -3.7214    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -1.5990    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5232   -2.0495    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -3.3598    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488   -1.0866    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2883    0.2582   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    1.1143   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3227    2.4987   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    0.6627   -0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328   -0.2532   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939    0.1821   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525   -0.8179    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.2430    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6686    0.1442    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9754    0.4788   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5904    1.5939    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576    2.9874   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    1.9735   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515   -2.6794    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3970   -4.2057    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5700   -1.4634    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9879    2.8030   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404    2.9488   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    2.9434    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    1.6964   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760   -1.8922    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0187   -0.8528    0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20  7  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv1652306222119252D          

 22 24  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
    0.0000   -1.6500    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
   -0.7145   -2.8875    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
    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579   -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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    2.8579    0.8250    0.0000 O   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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 14 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043838

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3

> <INCHI_KEY>
LZERJKGWTQYMBB-UHFFFAOYSA-N

> <FORMULA>
C17H14O5

> <MOLECULAR_WEIGHT>
298.2901

> <EXACT_MASS>
298.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.984313198755334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.998477245666666

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.361884817285098

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.365720393863971

> <JCHEM_PKA_STRONGEST_BASIC>
-4.485557942629643

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
81.87850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apigenin 7,4'-dimethyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043838
     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    6.7345    0.9736    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5458    1.7200   -0.0410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2913    1.1191   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    1.8925   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8958    1.3335   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -0.0528    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5995    0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333   -1.9471    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -2.5004    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -3.7214    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -1.5990    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5232   -2.0495    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -3.3598    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488   -1.0866    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2883    0.2582   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    1.1143   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3227    2.4987   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    0.6627   -0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328   -0.2532   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939    0.1821   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525   -0.8179    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.2430    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6686    0.1442    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9754    0.4788   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5904    1.5939    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576    2.9874   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    1.9735   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515   -2.6794    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3970   -4.2057    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5700   -1.4634    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9879    2.8030   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404    2.9488   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    2.9434    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    1.6964   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760   -1.8922    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0187   -0.8528    0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20  7  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
CONECT   20   16   21                                                       
CONECT   21   20                                                            
CONECT   22   14                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    NP0043838
HETATM    1  C1  UNL     1       6.735   0.974   0.013  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.546   1.720  -0.041  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.291   1.119  -0.019  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.152   1.892  -0.074  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.896   1.333  -0.054  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.718  -0.053   0.023  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.356  -0.600   0.041  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.133  -1.947   0.115  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.151  -2.500   0.134  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.329  -3.721   0.202  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.213  -1.599   0.073  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.523  -2.050   0.086  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.846  -3.360   0.157  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.549  -1.087   0.021  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.288   0.258  -0.053  1.00  0.00           C  
HETATM   16  O4  UNL     1      -5.368   1.114  -0.112  1.00  0.00           O  
HETATM   17  C13 UNL     1      -5.323   2.499  -0.190  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.984   0.663  -0.063  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.933  -0.253  -0.001  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.694   0.182  -0.014  1.00  0.00           O  
HETATM   21  C16 UNL     1       2.852  -0.818   0.077  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.110  -0.243   0.057  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.669   0.144   0.765  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.975   0.479  -0.970  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.590   1.594   0.336  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.258   2.987  -0.135  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.043   1.973  -0.098  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.951  -2.679   0.165  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.397  -4.206   0.210  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.570  -1.463   0.033  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.988   2.803  -1.051  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.340   2.949  -0.310  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.832   2.943   0.714  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.743   1.696  -0.119  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.776  -1.892   0.137  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.019  -0.853   0.100  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   21
CONECT    7    8    8   20
CONECT    8    9   28
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   16   18
CONECT   16   17
CONECT   17   31   32   33
CONECT   18   19   19   34
CONECT   19   20
CONECT   21   22   22   35
CONECT   22   36
END

NP0043838
     RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
    6.7345    0.9736    0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5458    1.7200   -0.0410 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2913    1.1191   -0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1517    1.8925   -0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8958    1.3335   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7177   -0.0528    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5995    0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333   -1.9471    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -2.5004    0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3290   -3.7214    0.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -1.5990    0.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5232   -2.0495    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -3.3598    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5488   -1.0866    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2883    0.2582   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    1.1143   -0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3227    2.4987   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9842    0.6627   -0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328   -0.2532   -0.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6939    0.1821   -0.0136 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8525   -0.8179    0.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1104   -0.2430    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6686    0.1442    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9754    0.4788   -0.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5904    1.5939    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576    2.9874   -0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0432    1.9735   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515   -2.6794    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3970   -4.2057    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5700   -1.4634    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9879    2.8030   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3404    2.9488   -0.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    2.9434    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7435    1.6964   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760   -1.8922    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0187   -0.8528    0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 20  7  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
4',7-Dimethylapigenin	ChEBI
4,7-Dimethoxy-5-hydroxyflavone	ChEBI
Apigenin dimethylether	ChEBI
Genkwanin 4'-methyl ether	ChEBI
5-Hydroxy-4',7-dimethoxyflavone	HMDB
5-Hydroxy-7,4'-dimethoxyflavone	HMDB
4',7-Di-O-methylapigenin	HMDB
4'-Methoxytectochrysin	HMDB
4’,7-di-O-methylapigenin	HMDB
4’,7-dimethylapigenin	HMDB
4’-methoxytectochrysin	HMDB
5-Hydroxy-4’,7-dimethoxyflavone	HMDB
5-Hydroxy-7,4’-dimethoxyflavone	HMDB
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one	HMDB
7,4'-Di-O-methylapigenin	HMDB
7,4'-Dimethylapigenin	HMDB
7,4’-di-O-methylapigenin	HMDB
7,4’-dimethylapigenin	HMDB
7-Methylacacetin	HMDB
7-O-Methylacacetin	HMDB
Acacetin 7-methyl ether	HMDB
Apigenin 4',7-dimethyl ether	HMDB
Apigenin 4’,7-dimethyl ether	HMDB
Apigenin 7,4’-dimethyl ether	HMDB
Apigenin dimethyl ether	HMDB
Apigenin-7,4'-dimethyl ether	HMDB
Apigenin-7,4-dimethyl ether	HMDB
Apigenin-7,4’-dimethyl ether	HMDB
Genkwanin 4’-methyl ether	HMDB
Apigenin 7,4'-dimethyl ether	HMDB

Chemical Formula

C₁₇H₁₄O₅

Average Mass

298.2901 Da

Monoisotopic Mass

298.08412 Da

IUPAC Name

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

apigenin 7,4'-dimethyl ether

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3

InChI Key

LZERJKGWTQYMBB-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aleuritopteris farinosa	LOTUS Database	35616633
Alnus japonica	KNApSAcK Database	22123792
Anarrhinum forskahlii	KNApSAcK Database	22123792
Andrographis paniculata	KNApSAcK Database	22123792
Antirrhinum spp.	KNApSAcK Database	22123792
Artabotrys hexapetalus	LOTUS Database	35616633
Artabotrys uncinatus	KNApSAcK Database	22123792
Artemisia afra	KNApSAcK Database	22123792
Artemisia diffusa	KNApSAcK Database	22123792
Artemisia pontica	LOTUS Database	35616633
Baccharis crispa	KNApSAcK Database	22123792
Baccharis rhomboidalis	KNApSAcK Database	22123792
Baccharis tola	LOTUS Database	35616633
Baccharis trinervis	KNApSAcK Database	22123792
Betula nigra	KNApSAcK Database	22123792
Betula pendula	LOTUS Database	35616633
Betula platyphylla	LOTUS Database	35616633
Boesenbergia rotunda	LOTUS Database	35616633
Bombax anceps	LOTUS Database	35616633
Calea jamaicensis	LOTUS Database	35616633
Calea ternifolia	KNApSAcK Database	22123792
Callicarpa americana	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Cheilanthes grisea	KNApSAcK Database	22123792
Cistus clusii	KNApSAcK Database	22123792
Cistus spp.	KNApSAcK Database	22123792
Cota palaestina	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cunila angustifolia	KNApSAcK Database	22123792
Currania robertiana	-	KNApSAcK
Dorystoechas hastata	KNApSAcK Database	22123792
Escallonia pulverulenta	KNApSAcK Database	22123792
Eucryphia spp.	KNApSAcK Database	22123792
Gymnocarpium robertianum	LOTUS Database	35616633
Hieracium amplexicaule	KNApSAcK Database	22123792
Hyptis albida	KNApSAcK Database	22123792
Hyptis capitata	LOTUS Database	35616633
Isodon flavidus	KNApSAcK Database	22123792
Kaempferia parviflora	KNApSAcK Database	22123792
Leucas cephalotes	LOTUS Database	35616633
Leucas cephalotes SPRENG.	KNApSAcK Database	22123792
Lycopus virginicus	KNApSAcK Database	22123792
Marchesinia brachiata	KNApSAcK Database	22123792
Mirabilis viscosa	KNApSAcK Database	22123792
Monoclea gottschei	KNApSAcK Database	22123792
Montanoa leucantha	LOTUS Database	35616633
Nuxia sphaerocephala	KNApSAcK Database	22123792
Ocimum americanum L.var.pilosum (Willd.) Paton	KNApSAcK Database	22123792
Ocimum basilicum	Plant	KNApSAcK
Ocimum basilicum L.	KNApSAcK Database	22123792
Ocimum minimum L.	KNApSAcK Database	22123792
Ocimum x citriodorum Vis.	KNApSAcK Database	22123792
Ophyrosporus charrua	-	KNApSAcK
Origanum dictamnus	LOTUS Database	35616633
Oroxylum indicum	LOTUS Database	35616633
Passiflora foetida	KNApSAcK Database	22123792
Peperomia blanda	LOTUS Database	35616633
Peperomia dindygulensis Miq.	KNApSAcK Database	22123792
Peperomia leptostachya	LOTUS Database	35616633
Peperomia sui	KNApSAcK Database	22123792
Perovskia spp.	KNApSAcK Database	22123792
Piper peepuloides	KNApSAcK Database	22123792
Platycladus orientalis	LOTUS Database	35616633
Plectranthus fruticosus	LOTUS Database	35616633
Podocarpus fasciculus	LOTUS Database	35616633
Pongamia pinnata	LOTUS Database	35616633
Reboulia hemisphaerica	LOTUS Database	35616633
Rhus undulata	KNApSAcK Database	22123792
Rosmarinus officinalis	KNApSAcK Database	22123792
Salvia bucharica	LOTUS Database	35616633
Salvia dorrii	KNApSAcK Database	22123792
Salvia hydrangea	LOTUS Database	35616633
Salvia hypoleuca	KNApSAcK Database	22123792
Salvia lavandulifolia	KNApSAcK Database	22123792
Salvia macrosiphon	KNApSAcK Database	22123792
Salvia moorcroftiana	KNApSAcK Database	22123792
Salvia nicolsoniana	KNApSAcK Database	22123792
Salvia officinalis	KNApSAcK Database	22123792
Salvia palaestina	KNApSAcK Database	22123792
Salvia rosmarinus	Plant	KNApSAcK
Salvia sapinae	KNApSAcK Database	22123792
Salvia sclarea	KNApSAcK Database	22123792
Salvia spp.	KNApSAcK Database	22123792
Salvia staminea	LOTUS Database	35616633
Salvia syriaca	KNApSAcK Database	22123792
Salvia texana	KNApSAcK Database	22123792
Salvia verbenaca	KNApSAcK Database	22123792
Salvia yosgadensis	KNApSAcK Database	22123792
Sideritis marmorea	LOTUS Database	35616633
Sideritis spp.	KNApSAcK Database	22123792
Streptomyces avermitilis	LOTUS Database	35616633
Striga asiatica	KNApSAcK Database	22123792
Teucrium heterophyllum	LOTUS Database	35616633
Teucrium marum	KNApSAcK Database	22123792
Teucrium polium	KNApSAcK Database	22123792
Teucrium ramosissimum	KNApSAcK Database	22123792
Thymus piperella	KNApSAcK Database	22123792
Thymus vulgaris	LOTUS Database	35616633
Trocholejeunea sandvicensis	LOTUS Database	35616633
Trocholejeunea scandvicensis	KNApSAcK Database	22123792
Turnera diffusa	LOTUS Database	35616633
Veratrum dahuricum	LOTUS Database	35616633
Xanthorrhoea australis	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

4p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monohydroxyflavone (CHEBI:2769 )
dimethoxyflavone (CHEBI:2769 )
flavones (C10019 )
Flavones and Flavonols (LMPK12111029 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	515.00 to 516.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	19.57 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.444 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	3.56	ALOGPS
logP	3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.37	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.88 m³·mol⁻¹	ChemAxon
Polarizability	30.98 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

HMDB0132454

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281601

PDB ID

Not Available

ChEBI ID

2769

Good Scents ID

rw1504761

References

General References

Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
Yu ZW, Zhu HY, Yang XS, Sun QY, Hao XJ: [Study on chemical constituents from Incarvillea arguta and their accelerating PC-12 cell differentiation]. Zhongguo Zhong Yao Za Zhi. 2005 Sep;30(17):1335-8. [PubMed:16323541 ]
Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing NP-Card for Apigenin 7,4'-dimethyl ether (NP0043838)

MOL for NP0043838 (Apigenin 7,4'-dimethyl ether)

3D MOL for NP0043838 (Apigenin 7,4'-dimethyl ether)

3D SDF for NP0043838 (Apigenin 7,4'-dimethyl ether)

3D-SDF for NP0043838 (Apigenin 7,4'-dimethyl ether)

PDB for NP0043838 (Apigenin 7,4'-dimethyl ether)

3D PDB for NP0043838 (Apigenin 7,4'-dimethyl ether)

SMILES for NP0043838 (Apigenin 7,4'-dimethyl ether)

INCHI for NP0043838 (Apigenin 7,4'-dimethyl ether)

Structure for NP0043838 (Apigenin 7,4'-dimethyl ether)

3D Structure for NP0043838 (Apigenin 7,4'-dimethyl ether)