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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:00 UTC

Update Date

2022-03-07 02:52:15 UTC

HMDB ID

HMDB0029677

Secondary Accession Numbers

HMDB29677

Metabolite Identification

Common Name

Zapotinin

Description

Zapotinin belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, zapotinin is considered to be a flavonoid. Based on a literature review very few articles have been published on Zapotinin.

Structure

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

HMDB0029677
     RDKit          3D
Zapotinin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.8854   -2.7703    2.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5210   -1.6268    1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.7074    0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -0.9155    1.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -0.0118    0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4142    1.0903    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0715    1.2895   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    2.4219   -0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7818    3.3239   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986    0.4140    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.5555   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153    1.5626   -0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    1.5647   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7327    2.5176   -1.7497 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    0.5609   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.5037   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    1.4773   -1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764   -0.5732   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140   -0.6296   -0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3888   -1.6225   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.5489    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1799   -1.5077    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215   -0.4496    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1522   -0.4039    0.2516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744   -2.5340    3.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915   -3.2849    1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -3.4817    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373   -1.8074    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424   -0.1849    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1587    1.8096   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010    2.8483   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240    3.7130   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    4.1569   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    2.3805   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8402    2.2971   -1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -1.7503   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -2.6247   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9392   -1.3538    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -2.4237    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -2.2744    1.0924 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 10  3  1  0
 24 11  1  0
 23 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END


  Mrv0541 05061304512D          

 24 26  0  0  0  0            999 V2000
    6.4302    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
    0.0000    0.8250    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
    6.4302   -0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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
    5.7158    0.0000    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
    2.8579    0.0000    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    0.0000    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
    5.0013   -0.4125    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    2.0625    0.0000 O   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
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 16 10  1  0  0  0  0
 16 13  2  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19 10  2  0  0  0  0
 20 18  1  0  0  0  0
 21  1  1  0  0  0  0
 21 11  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  1  0  0  0  0
 23  3  1  0  0  0  0
 23 14  1  0  0  0  0
 24 13  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029677

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-21-11-5-4-6-12(22-2)17(11)15-9-10(19)16-13(24-15)7-8-14(23-3)18(16)20/h4-9,20H,1-3H3

> <INCHI_KEY>
BFXYIQRRGIMMSR-UHFFFAOYSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.26996103679225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,6-dimethoxyphenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
2.84080598

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.87979316538786

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.13659887925086

> <JCHEM_PKA_STRONGEST_BASIC>
-4.35605829231806

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
88.34169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zapotinin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029677
     RDKit          3D
Zapotinin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.8854   -2.7703    2.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5210   -1.6268    1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.7074    0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -0.9155    1.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -0.0118    0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4142    1.0903    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0715    1.2895   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    2.4219   -0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7818    3.3239   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986    0.4140    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.5555   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153    1.5626   -0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    1.5647   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7327    2.5176   -1.7497 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    0.5609   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.5037   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    1.4773   -1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764   -0.5732   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140   -0.6296   -0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3888   -1.6225   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.5489    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1799   -1.5077    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215   -0.4496    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1522   -0.4039    0.2516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744   -2.5340    3.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915   -3.2849    1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -3.4817    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373   -1.8074    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424   -0.1849    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1587    1.8096   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010    2.8483   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240    3.7130   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    4.1569   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    2.3805   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8402    2.2971   -1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -1.7503   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -2.6247   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9392   -1.3538    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -2.4237    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -2.2744    1.0924 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 10  3  1  0
 24 11  1  0
 23 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  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      12.003   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -2.310   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      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   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      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    5    6                                                       
CONECT    5    4   11                                                       
CONECT    6    4   12                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9   10   15                                                       
CONECT   10    9   16   19                                                  
CONECT   11    5   17   21                                                  
CONECT   12    6   17   22                                                  
CONECT   13    7   16   24                                                  
CONECT   14    8   18   23                                                  
CONECT   15    9   17   24                                                  
CONECT   16   10   13   18                                                  
CONECT   17   11   12   15                                                  
CONECT   18   14   16   20                                                  
CONECT   19   10                                                            
CONECT   20   18                                                            
CONECT   21    1   11                                                       
CONECT   22    2   12                                                       
CONECT   23    3   14                                                       
CONECT   24   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0029677
HETATM    1  C1  UNL     1      -1.885  -2.770   2.007  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.521  -1.627   1.269  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.505  -0.707   0.902  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.821  -0.916   1.258  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.793  -0.012   0.898  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.414   1.090   0.182  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.072   1.290  -0.174  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.758   2.422  -0.897  1.00  0.00           O  
HETATM    9  C7  UNL     1      -3.782   3.324  -1.246  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.099   0.414   0.169  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.687   0.556  -0.165  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.115   1.563  -0.859  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.264   1.565  -1.105  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.733   2.518  -1.750  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.069   0.561  -0.657  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.432   0.504  -0.865  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.080   1.477  -1.553  1.00  0.00           O  
HETATM   18  C14 UNL     1       4.176  -0.573  -0.363  1.00  0.00           C  
HETATM   19  O5  UNL     1       5.514  -0.630  -0.567  1.00  0.00           O  
HETATM   20  C15 UNL     1       6.389  -1.623  -0.137  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.522  -1.549   0.328  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.180  -1.508   0.542  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.422  -0.450   0.053  1.00  0.00           C  
HETATM   24  O6  UNL     1       0.152  -0.404   0.252  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.274  -2.534   3.008  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.692  -3.285   1.414  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.069  -3.482   2.117  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.037  -1.807   1.821  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.842  -0.185   1.186  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.159   1.810  -0.110  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.601   2.848  -1.827  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.224   3.713  -0.284  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.403   4.157  -1.868  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.713   2.380  -1.235  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.840   2.297  -1.994  1.00  0.00           H  
HETATM   36  H12 UNL     1       7.162  -1.750  -0.951  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.925  -2.625  -0.019  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.939  -1.354   0.809  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.044  -2.424   0.751  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.623  -2.274   1.092  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   30
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   31   32   33
CONECT   10   11
CONECT   11   12   12   24
CONECT   12   13   34
CONECT   13   14   14   15
CONECT   15   16   16   23
CONECT   16   17   18
CONECT   17   35
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   36   37   38
CONECT   21   22   39
CONECT   22   23   23   40
CONECT   23   24
END

HMDB0029677
     RDKit          3D
Zapotinin
 40 42  0  0  0  0  0  0  0  0999 V2000
   -1.8854   -2.7703    2.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5210   -1.6268    1.2686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.7074    0.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213   -0.9155    1.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7926   -0.0118    0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4142    1.0903    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0715    1.2895   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    2.4219   -0.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7818    3.3239   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986    0.4140    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6869    0.5555   -0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153    1.5626   -0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2637    1.5647   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7327    2.5176   -1.7497 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689    0.5609   -0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.5037   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    1.4773   -1.5534 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764   -0.5732   -0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5140   -0.6296   -0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3888   -1.6225   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5221   -1.5489    0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1799   -1.5077    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215   -0.4496    0.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1522   -0.4039    0.2516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2744   -2.5340    3.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915   -3.2849    1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -3.4817    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0373   -1.8074    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8424   -0.1849    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1587    1.8096   -0.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6010    2.8483   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240    3.7130   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    4.1569   -1.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    2.3805   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8402    2.2971   -1.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1618   -1.7503   -0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251   -2.6247   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9392   -1.3538    0.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -2.4237    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -2.2744    1.0924 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 10  3  1  0
 24 11  1  0
 23 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 20 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-2',6,6'-trimethoxyflavone	HMDB

Chemical Formula

C₁₈H₁₆O₆

Average Molecular Weight

328.316

Monoisotopic Molecular Weight

328.094688244

IUPAC Name

2-(2,6-dimethoxyphenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one

Traditional Name

zapotinin

CAS Registry Number

14813-20-8

SMILES

COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2O

InChI Identifier

InChI=1S/C18H16O6/c1-21-11-5-4-6-12(22-2)17(11)15-9-10(19)16-13(24-15)7-8-14(23-3)18(16)20/h4-9,20H,1-3H3

InChI Key

BFXYIQRRGIMMSR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110090 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029677)
Cell membrane (HMDB: HMDB0029677)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029677)

Source

Endogenous

Endogenous (HMDB: HMDB0029677)

Plant

Plant (HMDB: HMDB0029677)

Exogenous

Food

Food (HMDB: HMDB0029677)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Exogenous (HMDB: HMDB0029677)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	224 - 225 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.83 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	0.024 g/L	ALOGPS
logP	3.34	ALOGPS
logP	2.84	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.34 m³·mol⁻¹	ChemAxon
Polarizability	33.27 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]+	176.559	31661259
DarkChem	[M-H]-	175.517	31661259
DeepCCS	[M+H]+	176.11	30932474
DeepCCS	[M-H]-	173.752	30932474
DeepCCS	[M-2H]-	207.288	30932474
DeepCCS	[M+Na]+	182.515	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	179.2	32859911
AllCCS	[M+Na]+	180.1	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	178.0	32859911
AllCCS	[M+HCOO]-	177.5	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.	8.5 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1115 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2547.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	331.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	194.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	245.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	572.9 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	700.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	142.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1265.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	531.0 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	1523.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	364.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	331.1 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	40.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zapotinin	COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2O	4306.9	Standard polar	33892256
Zapotinin	COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2O	3019.5	Standard non polar	33892256
Zapotinin	COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O1)C=CC(OC)=C2O	3108.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zapotinin,1TMS,isomer #1	COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O[Si](C)(C)C)C(OC)=CC=C2O1	3037.8	Semi standard non polar	33892256
Zapotinin,1TBDMS,isomer #1	COC1=CC=CC(OC)=C1C1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(OC)=CC=C2O1	3260.9	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 - Zapotinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2a-0956000000-80cd583d9c284972c404	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zapotinin GC-MS (1 TMS) - 70eV, Positive	splash10-05br-3239000000-eae7f4754c43b008a091	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zapotinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zapotinin 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 - Zapotinin ESI-TOF 10V, Negative-QTOF	splash10-004i-1009006000-afc42d1d6f09e7e77094	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 10V, Positive-QTOF	splash10-004i-0009000000-3ed3e15a00a8d0bbe97f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 20V, Positive-QTOF	splash10-004i-0009000000-38ff8f965e9d5c1d127c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 40V, Positive-QTOF	splash10-030s-3951000000-ce86eb8f7bc87eea4d5c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 10V, Negative-QTOF	splash10-004i-0009000000-373cb7d15dee9a2052bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 20V, Negative-QTOF	splash10-004i-0019000000-6918630582597e672986	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 40V, Negative-QTOF	splash10-03l0-7962000000-12ec39783e729b35cf0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 10V, Positive-QTOF	splash10-004i-0009000000-469c8ff76acf89a49db2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 20V, Positive-QTOF	splash10-004i-0009000000-469c8ff76acf89a49db2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 40V, Positive-QTOF	splash10-016r-0915000000-b96bc700f125b5d9e128	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 10V, Negative-QTOF	splash10-004i-0009000000-09da33804c51b0682244	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 20V, Negative-QTOF	splash10-004i-0009000000-2d0c8ed1c2dd4e90293c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zapotinin 40V, Negative-QTOF	splash10-0v00-0392000000-77fdc5ec5ce5e1f1d714	2021-09-22	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

FDB000862

KNApSAcK ID

C00003856

Chemspider ID

24843189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257595

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810871

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 Zapotinin (HMDB0029677)

MOL for HMDB0029677 (Zapotinin)

3D MOL for HMDB0029677 (Zapotinin)

3D SDF for HMDB0029677 (Zapotinin)

3D-SDF for HMDB0029677 (Zapotinin)

PDB for HMDB0029677 (Zapotinin)

3D PDB for HMDB0029677 (Zapotinin)

SMILES for HMDB0029677 (Zapotinin)

INCHI for HMDB0029677 (Zapotinin)

Structure for HMDB0029677 (Zapotinin)

3D Structure for HMDB0029677 (Zapotinin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra