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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:17 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030664

Secondary Accession Numbers

HMDB30664

Metabolite Identification

Common Name

3,3'-Dihydroxy-4',5,7-trimethoxyflavan

Description

3,3'-Dihydroxy-4',5,7-trimethoxyflavan belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. 3,3'-Dihydroxy-4',5,7-trimethoxyflavan has been detected, but not quantified in, a few different foods, such as chinese cinnamons (Cinnamomum aromaticum), green vegetables, and herbs and spices. This could make 3,3'-dihydroxy-4',5,7-trimethoxyflavan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Dihydroxy-4',5,7-trimethoxyflavan.

Structure

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

HMDB0030664
     RDKit          3D
3,3'-Dihydroxy-4',5,7-trimethoxyflavan
 44 46  0  0  0  0  0  0  0  0999 V2000
    0.2509    2.1121    4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387    0.7939    4.1654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568    0.2020    3.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989   -1.1186    3.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439   -1.8043    1.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617   -3.0709    1.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -4.3134    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9071   -1.0652    0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5677    0.2616    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462    0.8871    1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788    0.9151   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.2419   -1.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    0.6369   -1.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362    1.9113   -1.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    2.2724   -1.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    1.4164   -2.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252    1.7708   -2.2572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    3.0328   -1.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    0.1543   -2.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -0.6713   -3.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -0.1906   -2.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -1.2125   -1.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -1.6638   -2.8583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -1.6111   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824    2.6599    5.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168    2.7043    3.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    2.0880    4.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   -1.7080    3.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017   -5.0983    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746   -4.6089    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521   -4.5930    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741    1.9303    1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    0.6522   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    2.5383   -0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    3.2716   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    3.2830   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7622    3.0538   -1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931    3.8199   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1765   -1.5906   -3.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9494   -1.1894   -2.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847   -1.7964   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -1.2480   -3.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -2.7371   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -1.3184   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv0541 05061305252D          

 24 26  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    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
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    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
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    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
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 23 16  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0030664

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O6/c1-21-11-7-16(23-3)12-9-14(20)18(24-17(12)8-11)10-4-5-15(22-2)13(19)6-10/h4-8,14,18-20H,9H2,1-3H3

> <INCHI_KEY>
WCBCDLSKTYUDDL-UHFFFAOYSA-N

> <FORMULA>
C18H20O6

> <MOLECULAR_WEIGHT>
332.3478

> <EXACT_MASS>
332.125988372

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.48734967623115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.2327891833333338

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.898393310591281

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.786657323400123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2919391902841353

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
87.44659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030664
     RDKit          3D
3,3'-Dihydroxy-4',5,7-trimethoxyflavan
 44 46  0  0  0  0  0  0  0  0999 V2000
    0.2509    2.1121    4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387    0.7939    4.1654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568    0.2020    3.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989   -1.1186    3.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439   -1.8043    1.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617   -3.0709    1.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -4.3134    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9071   -1.0652    0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5677    0.2616    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462    0.8871    1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788    0.9151   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.2419   -1.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    0.6369   -1.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362    1.9113   -1.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    2.2724   -1.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    1.4164   -2.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252    1.7708   -2.2572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    3.0328   -1.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    0.1543   -2.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -0.6713   -3.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -0.1906   -2.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -1.2125   -1.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -1.6638   -2.8583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -1.6111   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824    2.6599    5.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168    2.7043    3.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    2.0880    4.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   -1.7080    3.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017   -5.0983    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746   -4.6089    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521   -4.5930    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741    1.9303    1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    0.6522   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    2.5383   -0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    3.2716   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3931    3.8199   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1765   -1.5906   -3.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9494   -1.1894   -2.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847   -1.7964   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -1.2480   -3.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -2.7371   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -1.3184   -0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
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 24 43  1  0
 24 44  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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    5   10                                                       
CONECT    5    4   15                                                       
CONECT    6   10   13                                                       
CONECT    7   11   16                                                       
CONECT    8   11   17                                                       
CONECT    9   12   14                                                       
CONECT   10    4    6   18                                                  
CONECT   11    7    8   21                                                  
CONECT   12    9   16   17                                                  
CONECT   13    6   15   19                                                  
CONECT   14    9   18   20                                                  
CONECT   15    5   13   22                                                  
CONECT   16    7   12   23                                                  
CONECT   17    8   12   24                                                  
CONECT   18   10   14   24                                                  
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21    1   11                                                       
CONECT   22    2   15                                                       
CONECT   23    3   16                                                       
CONECT   24   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030664
HETATM    1  C1  UNL     1       0.251   2.112   4.366  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.639   0.794   4.165  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.057   0.202   3.003  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.399  -1.119   3.016  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.844  -1.804   1.841  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.162  -3.071   1.902  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.457  -4.313   2.034  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.907  -1.065   0.706  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.568   0.262   0.673  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.146   0.887   1.816  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.679   0.915  -0.580  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.159   0.242  -1.747  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.278   0.637  -1.891  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.636   1.911  -1.427  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.959   2.272  -1.559  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.871   1.416  -2.119  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.225   1.771  -2.257  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.645   3.033  -1.800  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.530   0.154  -2.583  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.478  -0.671  -3.137  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.186  -0.191  -2.440  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.330  -1.212  -1.619  1.00  0.00           C  
HETATM   23  O6  UNL     1       1.880  -1.664  -2.858  1.00  0.00           O  
HETATM   24  C18 UNL     1       2.344  -1.611  -0.587  1.00  0.00           C  
HETATM   25  H1  UNL     1       0.982   2.660   5.034  1.00  0.00           H  
HETATM   26  H2  UNL     1       0.017   2.704   3.483  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.696   2.088   4.980  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.353  -1.708   3.919  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.702  -5.098   1.728  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.675  -4.609   3.122  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.452  -4.593   1.546  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.874   1.930   1.819  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.703   0.652  -2.610  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.117   2.538  -0.996  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.257   3.272  -1.197  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.244   3.283  -0.792  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.762   3.054  -1.657  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.393   3.820  -2.541  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.177  -1.591  -3.461  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.949  -1.189  -2.828  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.385  -1.796  -1.517  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.461  -1.248  -3.626  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.369  -2.737  -0.459  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.376  -1.318  -0.863  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    8    8
CONECT    6    7
CONECT    7   29   30   31
CONECT    8    9   24
CONECT    9   10   10   11
CONECT   10   32
CONECT   11   12
CONECT   12   13   22   33
CONECT   13   14   14   21
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   19
CONECT   17   18
CONECT   18   36   37   38
CONECT   19   20   21   21
CONECT   20   39
CONECT   21   40
CONECT   22   23   24   41
CONECT   23   42
CONECT   24   43   44
END

HMDB0030664
     RDKit          3D
3,3'-Dihydroxy-4',5,7-trimethoxyflavan
 44 46  0  0  0  0  0  0  0  0999 V2000
    0.2509    2.1121    4.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387    0.7939    4.1654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568    0.2020    3.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989   -1.1186    3.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439   -1.8043    1.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617   -3.0709    1.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572   -4.3134    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9071   -1.0652    0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5677    0.2616    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1462    0.8871    1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788    0.9151   -0.5797 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.2419   -1.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    0.6369   -1.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362    1.9113   -1.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    2.2724   -1.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    1.4164   -2.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2252    1.7708   -2.2572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    3.0328   -1.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    0.1543   -2.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -0.6713   -3.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1857   -0.1906   -2.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -1.2125   -1.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -1.6638   -2.8583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3437   -1.6111   -0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9824    2.6599    5.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0168    2.7043    3.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6961    2.0880    4.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532   -1.7080    3.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017   -5.0983    1.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746   -4.6089    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521   -4.5930    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8741    1.9303    1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    0.6522   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174    2.5383   -0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    3.2716   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2441    3.2830   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7622    3.0538   -1.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931    3.8199   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1765   -1.5906   -3.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9494   -1.1894   -2.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3847   -1.7964   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -1.2480   -3.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -2.7371   -0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759   -1.3184   -0.8635 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 12 22  1  0
 22 23  1  0
 22 24  1  0
 10  3  1  0
 21 13  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5,7-Tri-O-methylcatechin	HMDB
Catechin 5,7,4'-trimethyl ether	HMDB

Chemical Formula

C₁₈H₂₀O₆

Average Molecular Weight

332.3478

Monoisotopic Molecular Weight

332.125988372

IUPAC Name

2-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

Traditional Name

2-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

CAS Registry Number

105330-59-4

SMILES

COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1

InChI Identifier

InChI=1S/C18H20O6/c1-21-11-7-16(23-3)12-9-14(20)18(24-17(12)8-11)10-4-5-15(22-2)13(19)6-10/h4-8,14,18-20H,9H2,1-3H3

InChI Key

WCBCDLSKTYUDDL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030664)
Cytoplasm (HMDB: HMDB0030664)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030664)

Source

Endogenous

Endogenous (HMDB: HMDB0030664)

Plant

Plant (HMDB: HMDB0030664)

Exogenous

Food

Food (HMDB: HMDB0030664)

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030664)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 °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	0.17 g/L	ALOGPS
logP	1.91	ALOGPS
logP	2.23	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.45 m³·mol⁻¹	ChemAxon
Polarizability	34.49 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]+	180.177	31661259
DarkChem	[M-H]-	178.686	31661259
DeepCCS	[M+H]+	180.251	30932474
DeepCCS	[M-H]-	177.893	30932474
DeepCCS	[M-2H]-	211.952	30932474
DeepCCS	[M+Na]+	187.185	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.1	32859911
AllCCS	[M+NH4]+	183.5	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	182.3	32859911
AllCCS	[M+Na-2H]-	182.2	32859911
AllCCS	[M+HCOO]-	182.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dihydroxy-4',5,7-trimethoxyflavan	COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1	4229.4	Standard polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan	COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1	2877.2	Standard non polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan	COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC(O)=C(OC)C=C1	2942.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dihydroxy-4',5,7-trimethoxyflavan,1TMS,isomer #1	COC1=CC(OC)=C2CC(O[Si](C)(C)C)C(C3=CC=C(OC)C(O)=C3)OC2=C1	2890.7	Semi standard non polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan,1TMS,isomer #2	COC1=CC(OC)=C2CC(O)C(C3=CC=C(OC)C(O[Si](C)(C)C)=C3)OC2=C1	2924.0	Semi standard non polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan,2TMS,isomer #1	COC1=CC(OC)=C2CC(O[Si](C)(C)C)C(C3=CC=C(OC)C(O[Si](C)(C)C)=C3)OC2=C1	2791.5	Semi standard non polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan,1TBDMS,isomer #1	COC1=CC(OC)=C2CC(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(OC)C(O)=C3)OC2=C1	3149.8	Semi standard non polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan,1TBDMS,isomer #2	COC1=CC(OC)=C2CC(O)C(C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3167.8	Semi standard non polar	33892256
3,3'-Dihydroxy-4',5,7-trimethoxyflavan,2TBDMS,isomer #1	COC1=CC(OC)=C2CC(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3264.0	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 - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gbi-0927000000-b7ca1780828ea51a2749	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan GC-MS (2 TMS) - 70eV, Positive	splash10-03fr-5111900000-e5bae5891917ef367bc0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 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 - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 10V, Positive-QTOF	splash10-00lr-0309000000-23247d7f6b807b37ac95	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 20V, Positive-QTOF	splash10-014i-0902000000-b83908b22226c29e9dcc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 40V, Positive-QTOF	splash10-0079-1920000000-d34bf168e64c44d8f1ea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 10V, Negative-QTOF	splash10-001i-0109000000-c47d38b2809b7fb0b7f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 20V, Negative-QTOF	splash10-014i-0925000000-945232f7d9b93747b86c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 40V, Negative-QTOF	splash10-000i-2930000000-64b8770d4c6430497a7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 10V, Positive-QTOF	splash10-001i-0019000000-6cd7c88d3bd80121270d	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 20V, Positive-QTOF	splash10-00lr-0906000000-ee61fd4addbb81b67af9	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 40V, Positive-QTOF	splash10-014r-1941000000-471e03915afde59250a7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 10V, Negative-QTOF	splash10-001i-0009000000-368987f4c32345c339d2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 20V, Negative-QTOF	splash10-02aj-0497000000-29abda06a9d41c8cb287	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dihydroxy-4',5,7-trimethoxyflavan 40V, Negative-QTOF	splash10-053i-1590000000-76a5421b6ce1a197101a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002575

KNApSAcK ID

C00008816

Chemspider ID

35013252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67233312

PDB ID

Not Available

ChEBI ID

175243

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3,3'-Dihydroxy-4',5,7-trimethoxyflavan (HMDB0030664)

MOL for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

3D MOL for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

3D SDF for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

3D-SDF for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

PDB for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

3D PDB for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

SMILES for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

INCHI for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

Structure for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

3D Structure for HMDB0030664 (3,3'-Dihydroxy-4',5,7-trimethoxyflavan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra