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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:49:17 UTC

Update Date

2022-03-07 02:55:24 UTC

HMDB ID

HMDB0037570

Secondary Accession Numbers

HMDB37570

Metabolite Identification

Common Name

Demethoxykanugin

Description

Demethoxykanugin 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, demethoxykanugin is considered to be a flavonoid. Based on a literature review very few articles have been published on Demethoxykanugin.

Structure

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

HMDB0037570
     RDKit          3D
Demethoxykanugin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -5.8369   -2.5500   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4430   -2.6443   -0.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7051   -1.5011   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -0.2774   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    0.8761   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.7935    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    1.9207    0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0606    3.0280    0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081    1.7528    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    2.9458    0.7267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    3.6476   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    0.5224    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8799    0.2819    0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.1808    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    0.8562    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190   -0.3856    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -1.3082    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.9700    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -2.4985    0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225   -2.1807   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -1.0451    0.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339   -0.5057    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -0.4386   -0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653   -1.6012   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019   -3.5655   -0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3293   -1.9863   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0955   -2.0128   -1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195   -0.2189   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0880    1.8432   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    4.4945   -0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    4.0179   -0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    2.9277   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.1582    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    1.5835    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800   -1.7081   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3399   -3.0307    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052   -1.8759   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994   -2.5262   -0.2960 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  1  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 23  6  1  0
 18 13  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 24 38  1  0
M  END


  Mrv0541 05061309522D          

 24 27  0  0  0  0            999 V2000
   10.4970    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  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
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 17 10  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21  2  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 22 13  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 14  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037570

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O6/c1-20-11-4-5-12-14(8-11)24-17(18(21-2)16(12)19)10-3-6-13-15(7-10)23-9-22-13/h3-8H,9H2,1-2H3

> <INCHI_KEY>
UBKPBGYXBIXFFC-UHFFFAOYSA-N

> <FORMULA>
C18H14O6

> <MOLECULAR_WEIGHT>
326.3002

> <EXACT_MASS>
326.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.191651807849595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-3,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.2989503419999995

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3439675735941865

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
85.9199

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethoxykanugin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037570
     RDKit          3D
Demethoxykanugin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -5.8369   -2.5500   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4430   -2.6443   -0.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7051   -1.5011   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -0.2774   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    0.8761   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.7935    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    1.9207    0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0606    3.0280    0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081    1.7528    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    2.9458    0.7267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    3.6476   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    0.5224    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8799    0.2819    0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.1808    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    0.8562    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190   -0.3856    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -1.3082    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.9700    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -2.4985    0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225   -2.1807   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -1.0451    0.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339   -0.5057    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -0.4386   -0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653   -1.6012   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019   -3.5655   -0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3293   -1.9863   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0955   -2.0128   -1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195   -0.2189   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0880    1.8432   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    4.4945   -0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    4.0179   -0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    2.9277   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.1582    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    1.5835    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800   -1.7081   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3399   -3.0307    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052   -1.8759   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994   -2.5262   -0.2960 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  1  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 23  6  1  0
 18 13  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 24 38  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      19.594   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.927   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.593   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.593   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.221   5.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.927   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.926  -0.237   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      18.261   4.383   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.127   6.399   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.127   3.907   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.926   4.383   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    6   10                                                       
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    3   13                                                       
CONECT    7   10   15                                                       
CONECT    8   11   14                                                       
CONECT    9   22   23                                                       
CONECT   10    3    7   17                                                  
CONECT   11    4    8   20                                                  
CONECT   12    5   14   16                                                  
CONECT   13    6   15   22                                                  
CONECT   14    8   12   24                                                  
CONECT   15    7   13   23                                                  
CONECT   16   12   18   19                                                  
CONECT   17   10   18   24                                                  
CONECT   18   16   17   21                                                  
CONECT   19   16                                                            
CONECT   20    1   11                                                       
CONECT   21    2   18                                                       
CONECT   22    9   13                                                       
CONECT   23    9   15                                                       
CONECT   24   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0037570
HETATM    1  C1  UNL     1      -5.837  -2.550  -0.870  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.443  -2.644  -0.685  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.705  -1.501  -0.434  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.340  -0.277  -0.368  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.620   0.876  -0.119  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.234   0.793   0.067  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.490   1.921   0.314  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.061   3.028   0.374  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.108   1.753   0.487  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.568   2.946   0.727  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.992   3.648  -0.456  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.473   0.522   0.415  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.880   0.282   0.584  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.796   1.181   1.027  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.167   0.856   1.119  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.619  -0.386   0.763  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.702  -1.308   0.313  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.380  -0.970   0.232  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.351  -2.498   0.004  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.722  -2.181  -0.136  1.00  0.00           C  
HETATM   21  O5  UNL     1       5.847  -1.045   0.720  1.00  0.00           O  
HETATM   22  O6  UNL     1      -0.334  -0.506   0.170  1.00  0.00           O  
HETATM   23  C17 UNL     1      -1.618  -0.439  -0.004  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.365  -1.601  -0.258  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.302  -3.565  -0.846  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.329  -1.986  -0.039  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.095  -2.013  -1.804  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.419  -0.219  -0.513  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.088   1.843  -0.061  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.644   4.494  -0.179  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.076   4.018  -0.978  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.560   2.928  -1.073  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.505   2.158   1.345  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.879   1.584   1.473  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.680  -1.708  -0.123  1.00  0.00           H  
HETATM   36  H12 UNL     1       6.340  -3.031   0.254  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.005  -1.876  -1.147  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.799  -2.526  -0.296  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   23
CONECT    7    8    8    9
CONECT    9   10   12   12
CONECT   10   11
CONECT   11   30   31   32
CONECT   12   13   22
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   18   35
CONECT   19   20
CONECT   20   21   36   37
CONECT   22   23
CONECT   23   24   24
CONECT   24   38
END

HMDB0037570
     RDKit          3D
Demethoxykanugin
 38 41  0  0  0  0  0  0  0  0999 V2000
   -5.8369   -2.5500   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4430   -2.6443   -0.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7051   -1.5011   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401   -0.2774   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199    0.8761   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2337    0.7935    0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4901    1.9207    0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0606    3.0280    0.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081    1.7528    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    2.9458    0.7267 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9925    3.6476   -0.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4727    0.5224    0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8799    0.2819    0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.1808    1.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668    0.8562    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190   -0.3856    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7020   -1.3082    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -0.9700    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3509   -2.4985    0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225   -2.1807   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466   -1.0451    0.7201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339   -0.5057    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -0.4386   -0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3653   -1.6012   -0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3019   -3.5655   -0.8458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3293   -1.9863   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0955   -2.0128   -1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195   -0.2189   -0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0880    1.8432   -0.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6443    4.4945   -0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0762    4.0179   -0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600    2.9277   -1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5053    2.1582    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    1.5835    1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6800   -1.7081   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3399   -3.0307    0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052   -1.8759   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994   -2.5262   -0.2960 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  1  0
  9 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 23  6  1  0
 18 13  1  0
 21 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one	HMDB
3,7-Dimethoxy-3',4'-methylenedioxyflavone	HMDB
Desmethoxykanugin	HMDB

Chemical Formula

C₁₈H₁₄O₆

Average Molecular Weight

326.3002

Monoisotopic Molecular Weight

326.07903818

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

demethoxykanugin

CAS Registry Number

1668-33-3

SMILES

COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C18H14O6/c1-20-11-4-5-12-14(8-11)24-17(18(21-2)16(12)19)10-3-6-13-15(7-10)23-9-22-13/h3-8H,9H2,1-2H3

InChI Key

UBKPBGYXBIXFFC-UHFFFAOYSA-N

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111572 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037570)
Cell membrane (HMDB: HMDB0037570)

Source

Exogenous

Exogenous (HMDB: HMDB0037570)

Food

Food (HMDB: HMDB0037570)

Endogenous

Plant

Plant (HMDB: HMDB0037570)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037570)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	26.42 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	2.64	ALOGPS
logP	2.3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.92 m³·mol⁻¹	ChemAxon
Polarizability	33.19 Å³	ChemAxon
Number of Rings	4	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]+	175.79	31661259
DarkChem	[M-H]-	180.121	31661259
DeepCCS	[M+H]+	179.116	30932474
DeepCCS	[M-H]-	176.758	30932474
DeepCCS	[M-2H]-	210.824	30932474
DeepCCS	[M+Na]+	186.147	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.3	32859911
AllCCS	[M+NH4]+	178.2	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	177.8	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	176.1	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.	7.58 minutes	32390414
Predicted by Siyang on May 30, 2022	16.2108 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	2514.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	460.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	223.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	245.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	621.2 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	717.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	154.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1404.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	560.6 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	1600.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	445.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	464.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	430.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	462.5 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	26.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demethoxykanugin	COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1	4184.5	Standard polar	33892256
Demethoxykanugin	COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1	2904.1	Standard non polar	33892256
Demethoxykanugin	COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1	3021.3	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 - Demethoxykanugin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0961000000-d6c8cac9cea4d7772292	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethoxykanugin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethoxykanugin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 10V, Positive-QTOF	splash10-004i-0009000000-633ab32c4408d2246bcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 20V, Positive-QTOF	splash10-004i-0009000000-e2d5a6bc2de974ae9f47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 40V, Positive-QTOF	splash10-0uka-4891000000-6e496f33a3634eaafa12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 10V, Negative-QTOF	splash10-004i-0009000000-841185ca38cf4fca59ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 20V, Negative-QTOF	splash10-004i-0019000000-ae302011522f02f9fa52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 40V, Negative-QTOF	splash10-004j-2920000000-49f182898aaba9280bf4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 10V, Negative-QTOF	splash10-004i-0009000000-73983f66a563c6777817	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 20V, Negative-QTOF	splash10-004i-0319000000-701d8f0ebf2fd303fd09	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 40V, Negative-QTOF	splash10-015j-1911000000-622ff6036daf722ac55c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 10V, Positive-QTOF	splash10-004i-0009000000-fdece4c688aa8992d2ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 20V, Positive-QTOF	splash10-004i-0009000000-f176ed5b2ceb725e7afe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethoxykanugin 40V, Positive-QTOF	splash10-0ufr-1904000000-20fdf9ad0264b457d95c	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

FDB016658

KNApSAcK ID

C00005045

Chemspider ID

8557152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10381709

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1862191

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 Demethoxykanugin (HMDB0037570)

MOL for HMDB0037570 (Demethoxykanugin)

3D MOL for HMDB0037570 (Demethoxykanugin)

3D SDF for HMDB0037570 (Demethoxykanugin)

3D-SDF for HMDB0037570 (Demethoxykanugin)

PDB for HMDB0037570 (Demethoxykanugin)

3D PDB for HMDB0037570 (Demethoxykanugin)

SMILES for HMDB0037570 (Demethoxykanugin)

INCHI for HMDB0037570 (Demethoxykanugin)

Structure for HMDB0037570 (Demethoxykanugin)

3D Structure for HMDB0037570 (Demethoxykanugin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra