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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:14 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030659

Secondary Accession Numbers

HMDB30659

Metabolite Identification

Common Name

Takakin

Description

Takakin belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, takakin is considered to be a flavonoid. Takakin has been detected, but not quantified in, citrus. This could make takakin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Takakin.

Structure

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

HMDB0030659
     RDKit          3D
Takakin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.3220    0.1440    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4292    0.8126    0.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787    0.5106    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5637   -0.4075    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.6726    1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3016   -0.0479    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -0.3048    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -1.2085    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -1.4022    1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -2.2214    1.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -0.6967    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2164   -0.8740    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -1.7863    1.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9564   -0.1560   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3671    0.7383   -1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    1.4587   -2.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9783    0.9004   -1.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3877    1.7996   -2.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094    0.1938   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068    0.3468   -0.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    0.8727   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819    1.1451   -0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.2772    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2213   -0.9457    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3489    0.5133    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -0.8968    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779   -1.3987    1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -1.7777    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568   -1.9201    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210   -0.2914   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    2.1080   -3.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    1.9319   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1240    1.3775   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    1.8778   -1.4088 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
 15 17  1  0
 17 18  1  0
 17 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
 16 31  1  0
 18 32  1  0
 21 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061305252D          

 22 24  0  0  0  0            999 V2000
    7.8592   -1.2375    0.0000 C   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
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    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
    3.5724    1.2375    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20 15  1  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22 13  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030659

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-9-4-2-8(3-5-9)13-7-11(18)14-10(17)6-12(19)15(20)16(14)22-13/h2-7,17,19-20H,1H3

> <INCHI_KEY>
FIYPYRNWAKRRIU-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.72346056540464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7,8-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
2.5490178679999995

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.879702266959027

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.819409866567347

> <JCHEM_PKA_STRONGEST_BASIC>
-4.735586488659912

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
79.37710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
takakin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030659
     RDKit          3D
Takakin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.3220    0.1440    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4292    0.8126    0.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787    0.5106    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5637   -0.4075    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.6726    1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3016   -0.0479    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -0.3048    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -1.2085    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -1.4022    1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -2.2214    1.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -0.6967    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2164   -0.8740    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -1.7863    1.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9564   -0.1560   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3671    0.7383   -1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    1.4587   -2.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9783    0.9004   -1.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3877    1.7996   -2.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094    0.1938   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068    0.3468   -0.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    0.8727   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819    1.1451   -0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.2772    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2213   -0.9457    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3489    0.5133    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -0.8968    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779   -1.3987    1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -1.7777    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568   -1.9201    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210   -0.2914   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    2.1080   -3.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    1.9319   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1240    1.3775   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    1.8778   -1.4088 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
 15 17  1  0
 17 18  1  0
 17 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
 16 31  1  0
 18 32  1  0
 21 33  1  0
 22 34  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      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   12                                                       
CONECT    7   11   13                                                       
CONECT    8    2    3   13                                                  
CONECT    9    4    5   21                                                  
CONECT   10    6   14   17                                                  
CONECT   11    7   14   18                                                  
CONECT   12    6   15   19                                                  
CONECT   13    7    8   22                                                  
CONECT   14   10   11   16                                                  
CONECT   15   12   16   20                                                  
CONECT   16   14   15   22                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   15                                                            
CONECT   21    1    9                                                       
CONECT   22   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030659
HETATM    1  C1  UNL     1      -6.322   0.144   0.924  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.429   0.813   0.057  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.079   0.511   0.155  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.564  -0.407   1.052  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.211  -0.673   1.110  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.302  -0.048   0.288  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.131  -0.305   0.323  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.687  -1.208   1.198  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.056  -1.402   1.176  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.627  -2.221   1.959  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.834  -0.697   0.290  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.216  -0.874   0.248  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.757  -1.786   1.135  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.956  -0.156  -0.646  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.367   0.738  -1.505  1.00  0.00           C  
HETATM   16  O4  UNL     1       5.143   1.459  -2.408  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.978   0.900  -1.446  1.00  0.00           C  
HETATM   18  O5  UNL     1       2.388   1.800  -2.311  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.209   0.194  -0.560  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.907   0.347  -0.506  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.826   0.873  -0.611  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.182   1.145  -0.676  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.932   0.277   1.955  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.221  -0.946   0.695  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.349   0.513   0.861  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.283  -0.897   1.697  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.878  -1.399   1.832  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.102  -1.778   1.906  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.757  -1.920   1.111  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.021  -0.291  -0.679  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.669   2.108  -3.024  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.388   1.932  -2.285  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.124   1.378  -1.270  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.494   1.878  -1.409  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   17
CONECT   16   31
CONECT   17   18   19   19
CONECT   18   32
CONECT   19   20
CONECT   21   22   22   33
CONECT   22   34
END

HMDB0030659
     RDKit          3D
Takakin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.3220    0.1440    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4292    0.8126    0.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787    0.5106    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5637   -0.4075    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.6726    1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3016   -0.0479    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309   -0.3048    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -1.2085    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -1.4022    1.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -2.2214    1.9587 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -0.6967    0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2164   -0.8740    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7574   -1.7863    1.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9564   -0.1560   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3671    0.7383   -1.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1427    1.4587   -2.4075 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9783    0.9004   -1.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3877    1.7996   -2.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2094    0.1938   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9068    0.3468   -0.5057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8256    0.8727   -0.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1819    1.1451   -0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.2772    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2213   -0.9457    0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3489    0.5133    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2827   -0.8968    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8779   -1.3987    1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -1.7777    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568   -1.9201    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210   -0.2914   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    2.1080   -3.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3878    1.9319   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1240    1.3775   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4940    1.8778   -1.4088 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
 15 17  1  0
 17 18  1  0
 17 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
 16 31  1  0
 18 32  1  0
 21 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7,8-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
5,7,8-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
Isoscutellarein 4'-methyl ether	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

5,7,8-trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

takakin

CAS Registry Number

51876-19-8

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C=C2O

InChI Identifier

InChI=1S/C16H12O6/c1-21-9-4-2-8(3-5-9)13-7-11(18)14-10(17)6-12(19)15(20)16(14)22-13/h2-7,17,19-20H,1H3

InChI Key

FIYPYRNWAKRRIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111364 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	275 - 277 °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	0.077 g/L	ALOGPS
logP	3.15	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	29.72 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]+	170.209	31661259
DarkChem	[M-H]-	173.05	31661259
DeepCCS	[M+H]+	171.102	30932474
DeepCCS	[M-H]-	168.744	30932474
DeepCCS	[M-2H]-	202.446	30932474
DeepCCS	[M+Na]+	177.841	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	164.7	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	167.5	32859911
AllCCS	[M+HCOO]-	166.9	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.	6.77 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3846 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.14 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2607.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	330.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	512.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	643.4 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	682.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	147.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1075.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	475.9 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	1491.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	509.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	204.8 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	154.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Takakin	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C=C2O	4776.4	Standard polar	33892256
Takakin	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C=C2O	3181.5	Standard non polar	33892256
Takakin	COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C=C2O	3042.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Takakin,1TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C(O[Si](C)(C)C)=C3O2)C=C1	3288.5	Semi standard non polar	33892256
Takakin,1TMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C(O)=C3O2)C=C1	3309.5	Semi standard non polar	33892256
Takakin,1TMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C(O)=C3O2)C=C1	3315.7	Semi standard non polar	33892256
Takakin,2TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C(O[Si](C)(C)C)=C3O2)C=C1	3249.0	Semi standard non polar	33892256
Takakin,2TMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3O2)C=C1	3183.5	Semi standard non polar	33892256
Takakin,2TMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O)=C3O2)C=C1	3253.4	Semi standard non polar	33892256
Takakin,3TMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3O2)C=C1	3141.1	Semi standard non polar	33892256
Takakin,1TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3526.2	Semi standard non polar	33892256
Takakin,1TBDMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C3O2)C=C1	3555.7	Semi standard non polar	33892256
Takakin,1TBDMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O)=C3O2)C=C1	3560.1	Semi standard non polar	33892256
Takakin,2TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3715.8	Semi standard non polar	33892256
Takakin,2TBDMS,isomer #2	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3686.2	Semi standard non polar	33892256
Takakin,2TBDMS,isomer #3	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O)=C3O2)C=C1	3740.2	Semi standard non polar	33892256
Takakin,3TBDMS,isomer #1	COC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3O2)C=C1	3863.3	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 - Takakin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0490000000-8c1ab051bcc5e574a35c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Takakin GC-MS (3 TMS) - 70eV, Positive	splash10-0udl-3515960000-27c8c1e9662cc9dd39dc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Takakin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Takakin 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 - Takakin 10V, Positive-QTOF	splash10-0udi-0019000000-29124aa9691ed7cd6bbb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 20V, Positive-QTOF	splash10-0udi-0149000000-fc0e4ba793b9fdd9fb9f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 40V, Positive-QTOF	splash10-00kf-3960000000-42a969a82f0722dba0c4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 10V, Negative-QTOF	splash10-0002-0090000000-a32c2d363c039be66cc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 20V, Negative-QTOF	splash10-0002-0090000000-8ef0f3a05aa5a7261f0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 40V, Negative-QTOF	splash10-001i-3690000000-07cd5837698acda92e0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 10V, Negative-QTOF	splash10-0002-0090000000-79172b4191eb0ab50b2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 20V, Negative-QTOF	splash10-001i-0090000000-a7310606d67b19a35738	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 40V, Negative-QTOF	splash10-052b-0490000000-403636d8344a366d6b3f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 10V, Positive-QTOF	splash10-0udi-0009000000-4cf9dd217b03f450a62e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 20V, Positive-QTOF	splash10-0udi-0039000000-21f9279ab01ca5ee3dd4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Takakin 40V, Positive-QTOF	splash10-0a4i-0190000000-b0fdcc99e567342ff495	2021-09-23	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

FDB002569

KNApSAcK ID

C00003851

Chemspider ID

24844227

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44258588

PDB ID

Not Available

ChEBI ID

Not Available

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Takakin → 6-{[7,8-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Takakin → 6-{[5,8-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Takakin (HMDB0030659)

MOL for HMDB0030659 (Takakin)

3D MOL for HMDB0030659 (Takakin)

3D SDF for HMDB0030659 (Takakin)

3D-SDF for HMDB0030659 (Takakin)

PDB for HMDB0030659 (Takakin)

3D PDB for HMDB0030659 (Takakin)

SMILES for HMDB0030659 (Takakin)

INCHI for HMDB0030659 (Takakin)

Structure for HMDB0030659 (Takakin)

3D Structure for HMDB0030659 (Takakin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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