NP-MRD: Showing NP-Card for 7,3',4'-Trimethoxyisoflavone (NP0056504)

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Record Information

Version

2.0

Created at

2022-04-28 02:16:12 UTC

Updated at

2022-04-28 02:16:12 UTC

NP-MRD ID

NP0056504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,3',4'-Trimethoxyisoflavone

Description

Cabreuvin belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, cabreuvin is considered to be a flavonoid lipid molecule. 7,3',4'-Trimethoxyisoflavone is found in Araucaria angustifolia, Calopogonium mucunoides, Muntingia calabura, Myrocarpus fastigiatus, Myroxylon balsamum , Myroxylon peruiferum and Senna alata. Cabreuvin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    6.9892    0.4604    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4027   -0.7788    0.4203 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0176   -0.8780    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -2.0536    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9965   -2.1491    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2064   -1.0742    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -1.1469    0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -2.2293    0.5570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1214   -0.0411   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262   -0.0699   -0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0314   -1.1079   -0.7602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4093   -1.1432   -0.8253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1064   -0.0775   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4804   -0.0587   -0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2544   -1.0944   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    0.9947    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2103    2.0344    0.8323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    3.1619    1.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    0.9694    0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8084    1.1069   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175    1.1252   -0.3809 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415    0.0976   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104    0.2016    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6050    0.8012   -0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6964    1.1884    0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0977    0.3846    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9446   -2.9353    1.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -3.1032    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -1.9503   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360   -1.9913   -1.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3071   -1.0131   -0.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1930   -1.0991   -2.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8376   -2.0652   -0.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428    3.5181    0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3716    4.0465    1.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4503    3.0134    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.8323    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516    2.0062   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7063    1.1172   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 23 22  1  0
 22  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 20  2  0
 20 21  1  0
  9 10  1  0
 10 19  2  0
 19 16  1  0
 16 17  1  0
 17 18  1  0
 16 13  2  0
 13 14  1  0
 14 15  1  0
 13 12  1  0
 12 11  2  0
  4  3  1  0
 11 10  1  0
 21 22  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 39  1  0
  5 28  1  0
  4 27  1  0
 20 38  1  0
 19 37  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 12 30  1  0
 11 29  1  0
M  END

  Mrv0541 05061305262D          

 23 25  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
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   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
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    4.2868    2.4750    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
    2.1434    2.0625    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
    5.7158    3.3000    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
    5.0013    3.7125    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   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
  6  5  2  0  0  0  0
  7  4  2  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 12  9  2  0  0  0  0
 13  6  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17  8  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20  1  1  0  0  0  0
 20 12  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  3  1  0  0  0  0
 22 17  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC(OC)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-20-12-5-6-13-16(9-12)23-10-14(18(13)19)11-4-7-15(21-2)17(8-11)22-3/h4-10H,1-3H3

> <INCHI_KEY>
UKWLNMIPRJLYGH-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.3166

> <EXACT_MASS>
312.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.88560435976248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.8645545576666667

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.356929092278714

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
85.12979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cabreuvin

> <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      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    7   11                                                       
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7    4   15                                                       
CONECT    8   11   17                                                       
CONECT    9   12   16                                                       
CONECT   10   14   23                                                       
CONECT   11    4    8   14                                                  
CONECT   12    5    9   20                                                  
CONECT   13    6   16   18                                                  
CONECT   14   10   11   18                                                  
CONECT   15    7   17   21                                                  
CONECT   16    9   13   23                                                  
CONECT   17    8   15   22                                                  
CONECT   18   13   14   19                                                  
CONECT   19   18                                                            
CONECT   20    1   12                                                       
CONECT   21    2   15                                                       
CONECT   22    3   17                                                       
CONECT   23   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3'4'7-Trimethoxyisoflavone	HMDB
73'4'-Trimethoxyisoflavone	HMDB
3',4',7-Trimethoxyisoflavone	HMDB
3-(3,4-Dimethoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	HMDB
3-(3,4-Dimethoxyphenyl)-7-methoxy-4H-chromen-4-one	HMDB
7,3',4'-Trimethoxyisoflavone	HMDB
7-Methoxy-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one	HMDB

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3166 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

3-(3,4-dimethoxyphenyl)-7-methoxy-4H-chromen-4-one

Traditional Name

cabreuvin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC(OC)=C(OC)C=C1

InChI Identifier

InChI=1S/C18H16O5/c1-20-12-5-6-13-16(9-12)23-10-14(18(13)19)11-4-7-15(21-2)17(8-11)22-3/h4-10H,1-3H3

InChI Key

UKWLNMIPRJLYGH-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
Araucaria angustifolia	Plant	KNApSAcK
Calopogonium mucunoides	Plant	KNApSAcK
Muntingia calabura	LOTUS Database	35616633
Myrocarpus fastigiatus	Plant	KNApSAcK
Myroxylon balsamum	Plant	KNApSAcK
Myroxylon peruiferum	Plant	KNApSAcK
Senna alata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

3p-methoxyisoflavone
4p-o-methylisoflavone
7-o-methylisoflavone
Isoflavone
Chromone
Benzopyran
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050060 )

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	3.23	ALOGPS
logP	2.86	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.13 m³·mol⁻¹	ChemAxon
Polarizability	32.89 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

HMDB0030679

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002596

KNApSAcK ID

C00009405

Chemspider ID

545876

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628528

PDB ID

Not Available

ChEBI ID

112111

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7,3',4'-Trimethoxyisoflavone (NP0056504)

MOL for NP0056504 (7,3',4'-Trimethoxyisoflavone)

3D MOL for NP0056504 (7,3',4'-Trimethoxyisoflavone)

3D SDF for NP0056504 (7,3',4'-Trimethoxyisoflavone)

3D-SDF for NP0056504 (7,3',4'-Trimethoxyisoflavone)

PDB for NP0056504 (7,3',4'-Trimethoxyisoflavone)

3D PDB for NP0056504 (7,3',4'-Trimethoxyisoflavone)

SMILES for NP0056504 (7,3',4'-Trimethoxyisoflavone)

INCHI for NP0056504 (7,3',4'-Trimethoxyisoflavone)

Structure for NP0056504 (7,3',4'-Trimethoxyisoflavone)

3D Structure for NP0056504 (7,3',4'-Trimethoxyisoflavone)