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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:23 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030679

Secondary Accession Numbers

HMDB30679

Metabolite Identification

Common Name

Cabreuvin

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. Based on a literature review very few articles have been published on Cabreuvin.

Structure

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

HMDB0030679
     RDKit          3D
Cabreuvin
 39 41  0  0  0  0  0  0  0  0999 V2000
    7.2663   -0.1006   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2364   -1.0495   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9120   -0.6635   -0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6201    0.6726   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    1.0575   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808    0.1255   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.5133   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    1.7472   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424   -0.4291   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.0184   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372    1.1155   -0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    1.4969   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0820    0.8240   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    1.1906    0.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997    2.2712   -0.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6458   -0.2789    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254   -0.9832    1.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -2.1025    2.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203   -0.6643    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133   -1.7476   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723   -2.0811   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -1.2245   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839   -1.6027   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1947    0.5049    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2737    0.5957   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2269   -0.6688   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4075    1.4097   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    2.0885   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    1.6942   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    2.3583   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4681    2.0013   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8261    2.6311    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    3.0855   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301   -2.5920    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -1.7401    2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079   -2.8262    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967   -1.5294    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4977   -2.4853   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1342   -2.6326   -0.5842 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
  9 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23  3  1  0
 22  6  1  0
 19 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  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>
HMDB0030679

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0030679
     RDKit          3D
Cabreuvin
 39 41  0  0  0  0  0  0  0  0999 V2000
    7.2663   -0.1006   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2364   -1.0495   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9120   -0.6635   -0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6201    0.6726   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    1.0575   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808    0.1255   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.5133   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    1.7472   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424   -0.4291   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.0184   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372    1.1155   -0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    1.4969   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0820    0.8240   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    1.1906    0.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997    2.2712   -0.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6458   -0.2789    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254   -0.9832    1.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -2.1025    2.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203   -0.6643    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133   -1.7476   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723   -2.0811   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -1.2245   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839   -1.6027   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1947    0.5049    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2737    0.5957   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2269   -0.6688   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4075    1.4097   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    2.0885   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    1.6942   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    2.3583   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4681    2.0013   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8261    2.6311    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    3.0855   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301   -2.5920    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -1.7401    2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079   -2.8262    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967   -1.5294    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4977   -2.4853   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1342   -2.6326   -0.5842 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
  9 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23  3  1  0
 22  6  1  0
 19 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
M  END

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

COMPND    HMDB0030679
HETATM    1  C1  UNL     1       7.266  -0.101  -0.341  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.236  -1.049  -0.434  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.912  -0.663  -0.377  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.620   0.673  -0.228  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.296   1.058  -0.171  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.281   0.125  -0.262  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.963   0.513  -0.205  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.665   1.747  -0.066  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.042  -0.429  -0.297  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.420   0.018  -0.233  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.837   1.115  -0.948  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.168   1.497  -0.847  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.082   0.824  -0.063  1.00  0.00           C  
HETATM   14  O3  UNL     1      -5.395   1.191   0.044  1.00  0.00           O  
HETATM   15  C12 UNL     1      -6.000   2.271  -0.603  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.646  -0.279   0.651  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.525  -0.983   1.449  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.038  -2.102   2.160  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.320  -0.664   0.555  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.313  -1.748  -0.445  1.00  0.00           C  
HETATM   21  O5  UNL     1       1.572  -2.081  -0.496  1.00  0.00           O  
HETATM   22  C17 UNL     1       2.562  -1.225  -0.413  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.884  -1.603  -0.469  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.195   0.505   0.580  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.274   0.596  -1.216  1.00  0.00           H  
HETATM   26  H3  UNL     1       8.227  -0.669  -0.275  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.408   1.410  -0.156  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.050   2.088  -0.055  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.171   1.694  -1.587  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.504   2.358  -1.406  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.468   2.001  -1.571  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.826   2.631   0.046  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.279   3.086  -0.712  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.830  -2.592   2.759  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.204  -1.740   2.804  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.608  -2.826   1.415  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.997  -1.529   1.120  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.498  -2.485  -0.517  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.134  -2.633  -0.584  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   22
CONECT    7    8    8    9
CONECT    9   10   20   20
CONECT   10   11   11   19
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   16
CONECT   14   15
CONECT   15   31   32   33
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   37
CONECT   20   21   38
CONECT   21   22
CONECT   22   23   23
CONECT   23   39
END

HMDB0030679
     RDKit          3D
Cabreuvin
 39 41  0  0  0  0  0  0  0  0999 V2000
    7.2663   -0.1006   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2364   -1.0495   -0.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9120   -0.6635   -0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6201    0.6726   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    1.0575   -0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2808    0.1255   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.5133   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    1.7472   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424   -0.4291   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.0184   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8372    1.1155   -0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1684    1.4969   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0820    0.8240   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    1.1906    0.0441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9997    2.2712   -0.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6458   -0.2789    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254   -0.9832    1.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -2.1025    2.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203   -0.6643    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3133   -1.7476   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723   -2.0811   -0.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -1.2245   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8839   -1.6027   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1947    0.5049    0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2737    0.5957   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2269   -0.6688   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4075    1.4097   -0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    2.0885   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    1.6942   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    2.3583   -1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4681    2.0013   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8261    2.6311    0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2788    3.0855   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8301   -2.5920    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -1.7401    2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079   -2.8262    1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9967   -1.5294    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4977   -2.4853   -0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1342   -2.6326   -0.5842 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
  9 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23  3  1  0
 22  6  1  0
 19 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

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 Molecular Weight

312.3166

Monoisotopic Molecular Weight

312.099773622

IUPAC Name

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

Traditional Name

cabreuvin

CAS Registry Number

1621-61-0

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030679)
Cell membrane (HMDB: HMDB0030679)

Source

Endogenous

Endogenous (HMDB: HMDB0030679)

Plant

Plant (HMDB: HMDB0030679)

Exogenous

Food

Food (HMDB: HMDB0030679)

Exogenous (HMDB: HMDB0030679)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.79	31661259
DarkChem	[M-H]-	176.216	31661259
DeepCCS	[M+H]+	178.76	30932474
DeepCCS	[M-H]-	176.402	30932474
DeepCCS	[M-2H]-	210.535	30932474
DeepCCS	[M+Na]+	185.762	30932474
AllCCS	[M+H]+	173.2	32859911
AllCCS	[M+H-H2O]+	169.6	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.4	32859911
AllCCS	[M-H]-	176.8	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.86 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5445 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2173.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	348.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	187.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	497.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	640.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	145.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1178.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	457.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1369.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	373.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cabreuvin	COC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC(OC)=C(OC)C=C1	3927.6	Standard polar	33892256
Cabreuvin	COC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC(OC)=C(OC)C=C1	2856.2	Standard non polar	33892256
Cabreuvin	COC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC(OC)=C(OC)C=C1	2939.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cabreuvin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0690000000-4af1402d353bb20c4911	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cabreuvin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cabreuvin , positive-QTOF	splash10-0fr2-0490000000-9a44484614920381d440	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 10V, Positive-QTOF	splash10-03di-0009000000-2cbec3877c995d5d6976	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 20V, Positive-QTOF	splash10-03di-0019000000-485c58f31ea6497e70db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 40V, Positive-QTOF	splash10-0ufr-2690000000-9528c01d1f9dd2adb176	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 10V, Negative-QTOF	splash10-03di-0009000000-30e7c515938ae721f48e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 20V, Negative-QTOF	splash10-03di-0029000000-79b1067e57f4fb54550c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 40V, Negative-QTOF	splash10-0pdj-2490000000-c550dd916a511a890e3c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 10V, Positive-QTOF	splash10-03di-0009000000-0c9c5e8761c67e87c624	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 20V, Positive-QTOF	splash10-03di-0019000000-0e4bfe4c3300043fc21d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 40V, Positive-QTOF	splash10-016r-0290000000-100c4cc485f7c77c2b8c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 10V, Negative-QTOF	splash10-03di-0009000000-a968dea78994eb63447d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 20V, Negative-QTOF	splash10-03di-0029000000-7d8e16dc5eaa4aa1a786	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuvin 40V, Negative-QTOF	splash10-002k-0290000000-ce74bdf5fd877c8bf46b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cabreuvin (HMDB0030679)

MOL for HMDB0030679 (Cabreuvin)

3D MOL for HMDB0030679 (Cabreuvin)

3D SDF for HMDB0030679 (Cabreuvin)

3D-SDF for HMDB0030679 (Cabreuvin)

PDB for HMDB0030679 (Cabreuvin)

3D PDB for HMDB0030679 (Cabreuvin)

SMILES for HMDB0030679 (Cabreuvin)

INCHI for HMDB0030679 (Cabreuvin)

Structure for HMDB0030679 (Cabreuvin)

3D Structure for HMDB0030679 (Cabreuvin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra