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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:00:13 UTC

Update Date

2021-09-26 22:54:43 UTC

HMDB ID

HMDB0245959

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Methoxy-5,7,3',4'-tetrahydroxyflavan

Description

2-Methoxy-5,7,3',4'-tetrahydroxyflavan, also known as 3-MTHF or 3',4',5,7-tetrahydroxy-3-methoxyflavan, 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. Based on a literature review very few articles have been published on 2-Methoxy-5,7,3',4'-tetrahydroxyflavan. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-methoxy-5,7,3',4'-tetrahydroxyflavan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-Methoxy-5,7,3',4'-tetrahydroxyflavan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245959
     RDKit          3D
2-Methoxy-5,7,3',4'-tetrahydroxyflavan
 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.4141   -0.9934    2.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.9328    1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266    0.3432    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903    0.9362    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.6652   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7893    1.0321   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932    1.6391    0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5195    0.7892   -1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503    0.1818   -2.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -0.0631   -3.5633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254   -0.1666   -2.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665    0.0696   -1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301   -0.2880   -1.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2981    0.3851   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -0.0763   -0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661   -1.4328   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -1.9012   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -1.0461   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6516   -1.5445   -0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842    0.3061   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979    1.2388   -0.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7714    0.7732   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -0.2835    3.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.6969    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4454   -1.9962    3.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3449    0.9523    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090    0.5328    1.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    2.0338    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075    1.8360    1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646    1.0674   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1568   -0.9536   -3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338   -0.6366   -3.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898    1.4618   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -2.1309   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4830   -2.9743   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4741   -0.9750   -0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703    1.0089   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    1.8392   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 14  3  1  0
 22 15  1  0
 12  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv1533004231522322D          

 22 24  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245959

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3

> <INCHI_KEY>
PDHSAQOQVUXZGQ-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.44633301091239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-5,7-diol

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
2.4382335189999997

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.6232949992153

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.004144524189943

> <JCHEM_PKA_STRONGEST_BASIC>
-4.077565856426833

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
78.7509

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
meciadanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245959
     RDKit          3D
2-Methoxy-5,7,3',4'-tetrahydroxyflavan
 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.4141   -0.9934    2.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.9328    1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266    0.3432    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903    0.9362    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.6652   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7893    1.0321   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932    1.6391    0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5195    0.7892   -1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503    0.1818   -2.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -0.0631   -3.5633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254   -0.1666   -2.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665    0.0696   -1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301   -0.2880   -1.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2981    0.3851   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -0.0763   -0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661   -1.4328   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -1.9012   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -1.0461   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6516   -1.5445   -0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842    0.3061   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979    1.2388   -0.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7714    0.7732   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -0.2835    3.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.6969    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4454   -1.9962    3.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3449    0.9523    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090    0.5328    1.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    2.0338    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075    1.8360    1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646    1.0674   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1568   -0.9536   -3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338   -0.6366   -3.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898    1.4618   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -2.1309   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4830   -2.9743   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4741   -0.9750   -0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703    1.0089   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    1.8392   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 14  3  1  0
 22 15  1  0
 12  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0245959
HETATM    1  C1  UNL     1      -0.414  -0.993   2.835  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.388  -0.933   1.701  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.327   0.343   1.190  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.690   0.936   1.119  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.449   0.665  -0.109  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.789   1.032  -0.156  1.00  0.00           C  
HETATM    7  O2  UNL     1       4.393   1.639   0.936  1.00  0.00           O  
HETATM    8  C6  UNL     1       4.519   0.789  -1.297  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.950   0.182  -2.415  1.00  0.00           C  
HETATM   10  O3  UNL     1       4.684  -0.063  -3.563  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.625  -0.167  -2.333  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.866   0.070  -1.188  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.530  -0.288  -1.120  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.298   0.385  -0.193  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.685  -0.076  -0.217  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.966  -1.433  -0.252  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.263  -1.901  -0.275  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.342  -1.046  -0.265  1.00  0.00           C  
HETATM   19  O5  UNL     1      -5.652  -1.544  -0.289  1.00  0.00           O  
HETATM   20  C15 UNL     1      -4.084   0.306  -0.230  1.00  0.00           C  
HETATM   21  O6  UNL     1      -5.098   1.239  -0.217  1.00  0.00           O  
HETATM   22  C16 UNL     1      -2.771   0.773  -0.206  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.089  -0.283   3.622  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.477  -0.697   2.597  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.445  -1.996   3.295  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.345   0.952   1.831  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.309   0.533   1.970  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.634   2.034   1.321  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.907   1.836   1.784  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.565   1.067  -1.353  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.157  -0.954  -3.618  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.134  -0.637  -3.161  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.290   1.462  -0.490  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.130  -2.131  -0.261  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.483  -2.974  -0.303  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.474  -0.975  -0.283  1.00  0.00           H  
HETATM   37  H15 UNL     1      -6.070   1.009  -0.232  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.542   1.839  -0.178  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4   14   26
CONECT    4    5   27   28
CONECT    5    6    6   12
CONECT    6    7    8
CONECT    7   29
CONECT    8    9    9   30
CONECT    9   10   11
CONECT   10   31
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14
CONECT   14   15   33
CONECT   15   16   16   22
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19   20
CONECT   19   36
CONECT   20   21   22   22
CONECT   21   37
CONECT   22   38
END

HMDB0245959
     RDKit          3D
2-Methoxy-5,7,3',4'-tetrahydroxyflavan
 38 40  0  0  0  0  0  0  0  0999 V2000
   -0.4141   -0.9934    2.8354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.9328    1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266    0.3432    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903    0.9362    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.6652   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7893    1.0321   -0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3932    1.6391    0.9363 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5195    0.7892   -1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503    0.1818   -2.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -0.0631   -3.5633 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254   -0.1666   -2.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8665    0.0696   -1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301   -0.2880   -1.1200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2981    0.3851   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -0.0763   -0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661   -1.4328   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -1.9012   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417   -1.0461   -0.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6516   -1.5445   -0.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842    0.3061   -0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0979    1.2388   -0.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7714    0.7732   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0888   -0.2835    3.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.6969    2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4454   -1.9962    3.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3449    0.9523    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090    0.5328    1.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341    2.0338    1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9075    1.8360    1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646    1.0674   -1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1568   -0.9536   -3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338   -0.6366   -3.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898    1.4618   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -2.1309   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4830   -2.9743   -0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4741   -0.9750   -0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0703    1.0089   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5416    1.8392   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 14  3  1  0
 22 15  1  0
 12  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-MTHF	HMDB
3',4',5,7-Tetrahydroxy-3-methoxyflavan	HMDB
3-O-Methylcatechin, (2R-trans)-isomer	HMDB
Meciadanol	HMDB
2-Methoxy-5,7,3',4'-tetrahydroxyflavan	MeSH

Chemical Formula

C₁₆H₁₆O₆

Average Molecular Weight

304.298

Monoisotopic Molecular Weight

304.094688235

IUPAC Name

2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2H-1-benzopyran-5,7-diol

Traditional Name

meciadanol

CAS Registry Number

Not Available

SMILES

COC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C16H16O6/c1-21-15-7-10-12(19)5-9(17)6-14(10)22-16(15)8-2-3-11(18)13(20)4-8/h2-6,15-20H,7H2,1H3

InChI Key

PDHSAQOQVUXZGQ-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
3-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	1.68	ALOGPS
logP	2.44	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	30.45 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
DeepCCS	[M+H]+	174.38	30932474
DeepCCS	[M-H]-	172.022	30932474
DeepCCS	[M-2H]-	204.909	30932474
DeepCCS	[M+Na]+	180.473	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.4	32859911
AllCCS	[M-H]-	169.8	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	168.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.0803 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1535.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	224.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	142.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	114.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	580.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	404.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	184.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	798.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	378.7 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	1175.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	408.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	327.1 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	115.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-5,7,3',4'-tetrahydroxyflavan	COC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1	4320.5	Standard polar	33892256
2-Methoxy-5,7,3',4'-tetrahydroxyflavan	COC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1	2995.6	Standard non polar	33892256
2-Methoxy-5,7,3',4'-tetrahydroxyflavan	COC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1	3110.8	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 - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-0971000000-4d8948386862a2ee2f1f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	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 - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan 10V, Positive-QTOF	splash10-0a4i-0139000000-157d4385e0271f06ecf4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan 20V, Positive-QTOF	splash10-059i-0901000000-bc0f60177079aa3dc81c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan 40V, Positive-QTOF	splash10-00fr-2940000000-8e0989042cf8fe085893	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan 10V, Negative-QTOF	splash10-0udi-0019000000-dd0993511ab8867d6b2e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan 20V, Negative-QTOF	splash10-00di-0390000000-416f7ee79c5792ea6b77	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-5,7,3',4'-tetrahydroxyflavan 40V, Negative-QTOF	splash10-0fe3-2932000000-cffb536b50b6f165fdab	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

43318

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meciadanol

METLIN ID

Not Available

PubChem Compound

47610

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2-Methoxy-5,7,3',4'-tetrahydroxyflavan (HMDB0245959)

MOL for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

3D MOL for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

3D SDF for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

3D-SDF for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

PDB for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

3D PDB for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

SMILES for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

INCHI for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

Structure for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

3D Structure for HMDB0245959 (2-Methoxy-5,7,3',4'-tetrahydroxyflavan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra