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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:50:28 UTC

Update Date

2022-03-07 02:56:33 UTC

HMDB ID

HMDB0040308

Secondary Accession Numbers

HMDB40308

Metabolite Identification

Common Name

5',8-Dihydroxy-3',4',7-trimethoxyflavan

Description

5',8-Dihydroxy-3',4',7-trimethoxyflavan belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. 5',8-Dihydroxy-3',4',7-trimethoxyflavan has been detected, but not quantified in, fruits. This could make 5',8-dihydroxy-3',4',7-trimethoxyflavan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5',8-Dihydroxy-3',4',7-trimethoxyflavan.

Structure

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

HMDB0040308
     RDKit          3D
5',8-Dihydroxy-3',4',7-trimethoxyflavan
 44 46  0  0  0  0  0  0  0  0999 V2000
    6.6945    0.5507    1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3872    0.0569    1.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069    0.1963    0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    0.8232   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7570    0.9684   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5117    0.4720   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -0.1608    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308   -0.3092    1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.9301    2.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -0.6166    0.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -1.0817   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3079   -0.5478   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575   -0.0422   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.4555   -1.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698    0.9587   -2.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383    0.4597   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    0.9625   -0.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3276    0.0450   -0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2969   -0.0432    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044   -0.0326    1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785   -0.5442    3.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0081   -0.5361    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759   -0.8248   -1.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    0.5808   -1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0241    0.1247    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3740    0.2515    2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7099    1.6418    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7023    1.2175   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9449    1.4494   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -1.2806    2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -2.2048   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -0.0066   -2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    1.3169   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.6822   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1599    0.6428   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5719   -0.5363    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.2762    3.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -0.1340    3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.6483    3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -0.9249    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -1.0387   -2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -1.5167   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    1.3130   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777    0.8769   -2.8965 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
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
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 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 11 23  1  0
 23 24  1  0
  8  3  1  0
 22 12  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
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 13 32  1  0
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 22 40  1  0
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 24 44  1  0
M  END


  Mrv0541 05061311452D          

 24 26  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
   -0.7145    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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  2  0  0  0  0
 16 14  2  0  0  0  0
 17 10  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  2  0  0  0  0
 18 15  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  1  0  0  0  0
 21  1  1  0  0  0  0
 21 14  1  0  0  0  0
 22  2  1  0  0  0  0
 22 15  1  0  0  0  0
 23  3  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040308

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(O)=C1OC)C1CCC2=C(O1)C(O)=C(OC)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O6/c1-21-14-7-5-10-4-6-13(24-17(10)16(14)20)11-8-12(19)18(23-3)15(9-11)22-2/h5,7-9,13,19-20H,4,6H2,1-3H3

> <INCHI_KEY>
GOKBMBGIUIOXRB-UHFFFAOYSA-N

> <FORMULA>
C18H20O6

> <MOLECULAR_WEIGHT>
332.3478

> <EXACT_MASS>
332.125988372

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
35.101932159751115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-8-ol

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.004127468666667

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.970638824198009

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.27783580719973

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325583158131412

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
88.066

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-8-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040308
     RDKit          3D
5',8-Dihydroxy-3',4',7-trimethoxyflavan
 44 46  0  0  0  0  0  0  0  0999 V2000
    6.6945    0.5507    1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3872    0.0569    1.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069    0.1963    0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    0.8232   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7570    0.9684   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5117    0.4720   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -0.1608    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308   -0.3092    1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.9301    2.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -0.6166    0.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -1.0817   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3079   -0.5478   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575   -0.0422   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.4555   -1.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698    0.9587   -2.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383    0.4597   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    0.9625   -0.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3276    0.0450   -0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2969   -0.0432    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044   -0.0326    1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785   -0.5442    3.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0081   -0.5361    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759   -0.8248   -1.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    0.5808   -1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0241    0.1247    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3740    0.2515    2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7099    1.6418    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7023    1.2175   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9449    1.4494   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -1.2806    2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -2.2048   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -0.0066   -2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    1.3169   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.6822   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1599    0.6428   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5719   -0.5363    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.2762    3.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -0.1340    3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.6483    3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -0.9249    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -1.0387   -2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -1.5167   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    1.3130   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777    0.8769   -2.8965 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
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 11 23  1  0
 23 24  1  0
  8  3  1  0
 22 12  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   6.160   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       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    6   10                                                       
CONECT    5    7   10                                                       
CONECT    6    4   13                                                       
CONECT    7    5   14                                                       
CONECT    8   11   12                                                       
CONECT    9   11   15                                                       
CONECT   10    4    5   17                                                  
CONECT   11    8    9   13                                                  
CONECT   12    8   18   19                                                  
CONECT   13    6   11   24                                                  
CONECT   14    7   16   21                                                  
CONECT   15    9   18   22                                                  
CONECT   16   14   17   20                                                  
CONECT   17   10   16   24                                                  
CONECT   18   12   15   23                                                  
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21    1   14                                                       
CONECT   22    2   15                                                       
CONECT   23    3   18                                                       
CONECT   24   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0040308
HETATM    1  C1  UNL     1       6.694   0.551   1.736  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.387   0.057   1.955  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.407   0.196   0.984  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.720   0.823  -0.199  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.757   0.968  -1.172  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.512   0.472  -0.909  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.175  -0.161   0.271  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.131  -0.309   1.246  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.834  -0.930   2.427  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.876  -0.617   0.408  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.071  -1.082  -0.657  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.308  -0.548  -0.589  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.957  -0.042  -1.694  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.252   0.455  -1.622  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.870   0.959  -2.774  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.938   0.460  -0.425  1.00  0.00           C  
HETATM   17  O5  UNL     1      -5.249   0.963  -0.348  1.00  0.00           O  
HETATM   18  C13 UNL     1      -6.328   0.045  -0.573  1.00  0.00           C  
HETATM   19  C14 UNL     1      -3.297  -0.043   0.683  1.00  0.00           C  
HETATM   20  O6  UNL     1      -4.004  -0.033   1.889  1.00  0.00           O  
HETATM   21  C15 UNL     1      -3.379  -0.544   3.067  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.008  -0.536   0.600  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.776  -0.825  -1.938  1.00  0.00           C  
HETATM   24  C18 UNL     1       1.392   0.581  -1.913  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.024   0.125   0.746  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.374   0.252   2.556  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.710   1.642   1.607  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.702   1.218  -0.413  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.945   1.449  -2.114  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.899  -1.281   2.575  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.043  -2.205  -0.522  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.495  -0.007  -2.669  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.807   1.317  -2.714  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.021  -0.682  -1.355  1.00  0.00           H  
HETATM   35  H11 UNL     1      -7.160   0.643  -0.975  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.572  -0.536   0.326  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.978  -0.276   3.949  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.356  -0.134   3.203  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.282  -1.648   3.016  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.539  -0.925   1.505  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.236  -1.039  -2.855  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.672  -1.517  -1.951  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.685   1.313  -1.470  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.778   0.877  -2.897  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   24
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   30
CONECT   10   11
CONECT   11   12   23   31
CONECT   12   13   13   22
CONECT   13   14   32
CONECT   14   15   16   16
CONECT   15   33
CONECT   16   17   19
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   20   22   22
CONECT   20   21
CONECT   21   37   38   39
CONECT   22   40
CONECT   23   24   41   42
CONECT   24   43   44
END

HMDB0040308
     RDKit          3D
5',8-Dihydroxy-3',4',7-trimethoxyflavan
 44 46  0  0  0  0  0  0  0  0999 V2000
    6.6945    0.5507    1.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3872    0.0569    1.9549 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069    0.1963    0.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    0.8232   -0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7570    0.9684   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5117    0.4720   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751   -0.1608    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308   -0.3092    1.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.9301    2.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -0.6166    0.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707   -1.0817   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3079   -0.5478   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575   -0.0422   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    0.4555   -1.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8698    0.9587   -2.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383    0.4597   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2489    0.9625   -0.3482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3276    0.0450   -0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2969   -0.0432    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044   -0.0326    1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3785   -0.5442    3.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0081   -0.5361    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759   -0.8248   -1.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    0.5808   -1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0241    0.1247    0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3740    0.2515    2.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7099    1.6418    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7023    1.2175   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9449    1.4494   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -1.2806    2.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -2.2048   -0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947   -0.0066   -2.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8066    1.3169   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0214   -0.6822   -1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1599    0.6428   -0.9749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5719   -0.5363    0.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.2762    3.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -0.1340    3.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817   -1.6483    3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -0.9249    1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2360   -1.0387   -2.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -1.5167   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    1.3130   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777    0.8769   -2.8965 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
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 11 23  1  0
 23 24  1  0
  8  3  1  0
 22 12  1  0
 24  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 11 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 24 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₆

Average Molecular Weight

332.3478

Monoisotopic Molecular Weight

332.125988372

IUPAC Name

2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-8-ol

Traditional Name

2-(3-hydroxy-4,5-dimethoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-8-ol

CAS Registry Number

133342-96-8

SMILES

COC1=CC(=CC(O)=C1OC)C1CCC2=C(O1)C(O)=C(OC)C=C2

InChI Identifier

InChI=1S/C18H20O6/c1-21-14-7-5-10-4-6-13(24-17(10)16(14)20)11-8-12(19)18(23-3)15(9-11)22-2/h5,7-9,13,19-20H,4,6H2,1-3H3

InChI Key

GOKBMBGIUIOXRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0040308)

Cellular substructure

Membrane (HMDB: HMDB0040308)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040308)

Source

Exogenous

Food

Food (HMDB: HMDB0040308)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0040308)

Not Available

Nutrient (HMDB: HMDB0040308)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	153 °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	0.094 g/L	ALOGPS
logP	2.58	ALOGPS
logP	3	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-4.3	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	88.07 m³·mol⁻¹	ChemAxon
Polarizability	35.1 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]+	178.395	31661259
DarkChem	[M-H]-	179.191	31661259
DeepCCS	[M+H]+	179.012	30932474
DeepCCS	[M-H]-	176.654	30932474
DeepCCS	[M-2H]-	210.728	30932474
DeepCCS	[M+Na]+	186.066	30932474
AllCCS	[M+H]+	179.7	32859911
AllCCS	[M+H-H2O]+	176.4	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.7	32859911
AllCCS	[M-H]-	182.6	32859911
AllCCS	[M+Na-2H]-	182.4	32859911
AllCCS	[M+HCOO]-	182.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5',8-Dihydroxy-3',4',7-trimethoxyflavan	COC1=CC(=CC(O)=C1OC)C1CCC2=C(O1)C(O)=C(OC)C=C2	4070.3	Standard polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan	COC1=CC(=CC(O)=C1OC)C1CCC2=C(O1)C(O)=C(OC)C=C2	2775.5	Standard non polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan	COC1=CC(=CC(O)=C1OC)C1CCC2=C(O1)C(O)=C(OC)C=C2	2861.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5',8-Dihydroxy-3',4',7-trimethoxyflavan,1TMS,isomer #1	COC1=CC=C2CCC(C3=CC(OC)=C(OC)C(O[Si](C)(C)C)=C3)OC2=C1O	2833.5	Semi standard non polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan,1TMS,isomer #2	COC1=CC(C2CCC3=CC=C(OC)C(O[Si](C)(C)C)=C3O2)=CC(O)=C1OC	2812.0	Semi standard non polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan,2TMS,isomer #1	COC1=CC(C2CCC3=CC=C(OC)C(O[Si](C)(C)C)=C3O2)=CC(O[Si](C)(C)C)=C1OC	2756.7	Semi standard non polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan,1TBDMS,isomer #1	COC1=CC=C2CCC(C3=CC(OC)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1O	3068.9	Semi standard non polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan,1TBDMS,isomer #2	COC1=CC(C2CCC3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3O2)=CC(O)=C1OC	3030.3	Semi standard non polar	33892256
5',8-Dihydroxy-3',4',7-trimethoxyflavan,2TBDMS,isomer #1	COC1=CC(C2CCC3=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1OC	3183.8	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 - 5',8-Dihydroxy-3',4',7-trimethoxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-0419000000-3d276d55292310f4c73e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan GC-MS (2 TMS) - 70eV, Positive	splash10-03di-1011900000-a32ee5648b719909c7a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5',8-Dihydroxy-3',4',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 - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 10V, Positive-QTOF	splash10-001i-0509000000-b438ab47b86f4384b584	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 20V, Positive-QTOF	splash10-0udi-0901000000-19585a4910f1bfad855a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 40V, Positive-QTOF	splash10-0udi-0900000000-a2337e208811823f9d2c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 10V, Negative-QTOF	splash10-001i-0109000000-fed10a5a929d0a5e2142	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 20V, Negative-QTOF	splash10-0ue9-0449000000-2f1132e45994f9e6651c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 40V, Negative-QTOF	splash10-0ap0-1490000000-b4cdd43acfa07fcb7937	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 10V, Positive-QTOF	splash10-001i-0009000000-c3320d46d0916728ee94	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 20V, Positive-QTOF	splash10-001i-0309000000-18f7aa278fe7f6f60d08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 40V, Positive-QTOF	splash10-0002-0981000000-8ec5d236dddf48996f49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 10V, Negative-QTOF	splash10-001i-0009000000-070a13f8a79ca9be0981	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 20V, Negative-QTOF	splash10-001i-0398000000-b7cfba5dcd9e0f8d7896	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5',8-Dihydroxy-3',4',7-trimethoxyflavan 40V, Negative-QTOF	splash10-0f9i-1691000000-831572c104a1db1cc0d0	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

FDB020031

KNApSAcK ID

Not Available

Chemspider ID

35014923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75072285

PDB ID

Not Available

ChEBI ID

169286

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 5',8-Dihydroxy-3',4',7-trimethoxyflavan (HMDB0040308)

MOL for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

3D MOL for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

3D SDF for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

3D-SDF for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

PDB for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

3D PDB for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

SMILES for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

INCHI for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

Structure for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

3D Structure for HMDB0040308 (5',8-Dihydroxy-3',4',7-trimethoxyflavan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra