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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:55 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030768

Secondary Accession Numbers

HMDB30768

Metabolite Identification

Common Name

2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran

Description

2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran, also known as 2-benzofuranyl-3-methoxy-4,5-methylenedioxyphenol or 6-(2-benzofuranyl)-7-methoxy-1,3-benzodioxol-5-ol, 9CI, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Based on a literature review very few articles have been published on 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran.

Structure

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

HMDB0030768
     RDKit          3D
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.3551   -0.8712    2.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    0.3431    1.6211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6894    0.1333    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    0.1072   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4116   -0.1002   -1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -0.2754   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013   -0.2513   -2.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -0.4310   -3.0565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -0.0397   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698    0.0587   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993    0.4949    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065    0.4269    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.7159    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.5358    1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1912    0.0533   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -0.2412   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283   -0.0561   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893   -0.2458   -1.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.0741   -1.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    0.4507   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029    0.2545    0.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0664   -1.7338    1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -0.7402    3.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387   -1.0660    2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -0.4351   -3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -0.4310   -2.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    0.8602    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.0929    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979    0.7622    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2087   -0.0915   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -0.6228   -1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5318    1.5206   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -0.1038    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
  9  3  1  0
 18 10  1  0
 21  4  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 20 32  1  0
 20 33  1  0
M  END

  Mrv0541 05061305292D          

 21 24  0  0  0  0            999 V2000
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3277    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0902    4.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382    2.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0902    2.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6777    3.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708    3.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18  1  1  0  0  0  0
 18 16  1  0  0  0  0
 19  8  1  0  0  0  0
 19 13  1  0  0  0  0
 20  8  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 21 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030768

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO2

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-18-16-14(10(17)7-13-15(16)20-8-19-13)12-6-9-4-2-3-5-11(9)21-12/h2-7,17H,8H2,1H3

> <INCHI_KEY>
ACHFSGOIKJNVJV-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.034730971065322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-ol

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.861592582666666

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.922899342289833

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6671343551338436

> <JCHEM_POLAR_SURFACE_AREA>
61.06

> <JCHEM_REFRACTIVITY>
74.1238

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030768
     RDKit          3D
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.3551   -0.8712    2.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    0.3431    1.6211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6894    0.1333    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    0.1072   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4116   -0.1002   -1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -0.2754   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013   -0.2513   -2.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -0.4310   -3.0565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -0.0397   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698    0.0587   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993    0.4949    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065    0.4269    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.7159    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.5358    1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1912    0.0533   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -0.2412   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283   -0.0561   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893   -0.2458   -1.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.0741   -1.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    0.4507   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029    0.2545    0.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0664   -1.7338    1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -0.7402    3.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387   -1.0660    2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -0.4351   -3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -0.4310   -2.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    0.8602    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.0929    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979    0.7622    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2087   -0.0915   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -0.6228   -1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5318    1.5206   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -0.1038    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
  9  3  1  0
 18 10  1  0
 21  4  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 20 32  1  0
 20 33  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       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.945   6.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.175   7.568   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.175   4.901   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.635   7.568   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.605   3.756   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.635   4.901   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.865   6.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.359   5.914   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   11                                                       
CONECT    6    9   12                                                       
CONECT    7   10   13                                                       
CONECT    8   19   20                                                       
CONECT    9    4    6   11                                                  
CONECT   10    7   14   17                                                  
CONECT   11    5    9   21                                                  
CONECT   12    6   14   21                                                  
CONECT   13    7   15   19                                                  
CONECT   14   10   12   16                                                  
CONECT   15   13   16   20                                                  
CONECT   16   14   15   18                                                  
CONECT   17   10                                                            
CONECT   18    1   16                                                       
CONECT   19    8   13                                                       
CONECT   20    8   15                                                       
CONECT   21   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0030768
HETATM    1  C1  UNL     1      -1.355  -0.871   2.388  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.403   0.343   1.621  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.689   0.133   0.263  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.053   0.107  -0.046  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.412  -0.100  -1.360  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.467  -0.275  -2.334  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.101  -0.251  -2.044  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.200  -0.431  -3.057  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.735  -0.040  -0.708  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.670   0.059  -0.343  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.199   0.495   0.854  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.607   0.427   0.764  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.648   0.716   1.603  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.971   0.536   1.208  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.191   0.053  -0.065  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.129  -0.241  -0.920  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.828  -0.056  -0.510  1.00  0.00           C  
HETATM   18  O3  UNL     1       1.689  -0.246  -1.090  1.00  0.00           O  
HETATM   19  O4  UNL     1      -4.814  -0.074  -1.351  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.278   0.451  -0.140  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.203   0.255   0.734  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.066  -1.734   1.779  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.608  -0.740   3.194  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.339  -1.066   2.831  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.791  -0.435  -3.346  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.764  -0.431  -2.982  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.751   0.860   1.756  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.437   1.093   2.595  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.798   0.762   1.866  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.209  -0.092  -0.386  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.310  -0.623  -1.926  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.532   1.521  -0.238  1.00  0.00           H  
HETATM   33  H12 UNL     1      -6.157  -0.104   0.261  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   21
CONECT    5    6    6   19
CONECT    6    7   25
CONECT    7    8    9    9
CONECT    8   26
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   27
CONECT   12   13   13   17
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   19   20
CONECT   20   21   32   33
END

HMDB0030768
     RDKit          3D
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.3551   -0.8712    2.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    0.3431    1.6211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6894    0.1333    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    0.1072   -0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4116   -0.1002   -1.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667   -0.2754   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1013   -0.2513   -2.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -0.4310   -3.0565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7355   -0.0397   -0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6698    0.0587   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1993    0.4949    0.8536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6065    0.4269    0.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.7159    1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9707    0.5358    1.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1912    0.0533   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -0.2412   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283   -0.0561   -0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6893   -0.2458   -1.0903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8137   -0.0741   -1.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    0.4507   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029    0.2545    0.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0664   -1.7338    1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   -0.7402    3.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387   -1.0660    2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905   -0.4351   -3.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -0.4310   -2.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    0.8602    1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    1.0929    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7979    0.7622    1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2087   -0.0915   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -0.6228   -1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5318    1.5206   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1566   -0.1038    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  1  0
 19 20  1  0
 20 21  1  0
  9  3  1  0
 18 10  1  0
 21  4  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 20 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Benzofuranyl-3-methoxy-4,5-methylenedioxyphenol	HMDB
6-(2-Benzofuranyl)-7-methoxy-1,3-benzodioxol-5-ol, 9ci	HMDB

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-ol

Traditional Name

6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-ol

CAS Registry Number

90996-89-7

SMILES

COC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO2

InChI Identifier

InChI=1S/C16H12O5/c1-18-16-14(10(17)7-13-15(16)20-8-19-13)12-6-9-4-2-3-5-11(9)21-12/h2-7,17H,8H2,1H3

InChI Key

ACHFSGOIKJNVJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Benzodioxole
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030768)
Cell membrane (HMDB: HMDB0030768)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030768)

Source

Endogenous

Endogenous (HMDB: HMDB0030768)

Plant

Poaceae (HMDB: HMDB0030768)

Exogenous

Food

Food (HMDB: HMDB0030768)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Exogenous (HMDB: HMDB0030768)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 °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	0.15 g/L	ALOGPS
logP	3.04	ALOGPS
logP	2.86	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.12 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	4	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]+	163.873	31661259
DarkChem	[M-H]-	164.2	31661259
DeepCCS	[M+H]+	170.195	30932474
DeepCCS	[M-H]-	167.838	30932474
DeepCCS	[M-2H]-	200.724	30932474
DeepCCS	[M+Na]+	176.289	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran	COC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO2	3646.7	Standard polar	33892256
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran	COC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO2	2267.7	Standard non polar	33892256
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran	COC1=C(C2=CC3=CC=CC=C3O2)C(O)=CC2=C1OCO2	2542.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran,1TMS,isomer #1	COC1=C2OCOC2=CC(O[Si](C)(C)C)=C1C1=CC2=CC=CC=C2O1	2631.8	Semi standard non polar	33892256
2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran,1TBDMS,isomer #1	COC1=C2OCOC2=CC(O[Si](C)(C)C(C)(C)C)=C1C1=CC2=CC=CC=C2O1	2885.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kai-1190000000-d3f912309ccfef752743	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran GC-MS (1 TMS) - 70eV, Positive	splash10-007o-7239000000-615e6fee44a136ebaa58	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 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 - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Positive-QTOF	splash10-000i-0090000000-8a163de7f38e28e475d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Positive-QTOF	splash10-000i-0090000000-0a95fe455860f0b5d375	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Positive-QTOF	splash10-0a4r-2190000000-bf45eec5c0811130f146	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Negative-QTOF	splash10-001i-0090000000-800c6b79a1f5bd990a90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Negative-QTOF	splash10-001i-0090000000-e074dfdae01df08fe202	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Negative-QTOF	splash10-0ffc-1290000000-491ad6a93b8233683c00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Positive-QTOF	splash10-000i-0090000000-edc9ea273e98ea6aa00a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Positive-QTOF	splash10-000i-0090000000-005cd0acf791ae456fca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Positive-QTOF	splash10-05mo-2490000000-e11c768c8bf884ab37dc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 10V, Negative-QTOF	splash10-001i-0090000000-549f6b30f75977e8ff35	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 20V, Negative-QTOF	splash10-001i-0390000000-5f15091431e0544a183e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran 40V, Negative-QTOF	splash10-0ul0-1290000000-2d37552d63c389935bd8	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-17	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

FDB002703

KNApSAcK ID

Not Available

Chemspider ID

9066636

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10891372

PDB ID

Not Available

ChEBI ID

103729

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

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

Reactions

2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran → 6-{[6-(1-benzofuran-2-yl)-7-methoxy-2H-1,3-benzodioxol-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran (HMDB0030768)

MOL for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

3D MOL for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

3D SDF for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

3D-SDF for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

PDB for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

3D PDB for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

SMILES for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

INCHI for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

Structure for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

3D Structure for HMDB0030768 (2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions