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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:57:56 UTC

Update Date

2022-03-07 02:56:57 UTC

HMDB ID

HMDB0041295

Secondary Accession Numbers

HMDB41295

Metabolite Identification

Common Name

7-Hydroxy-6-methoxy-alpha-pyrufuran

Description

7-Hydroxy-6-methoxy-alpha-pyrufuran, also known as 1,3,4,6-tetramethoxy-2,7-dibenzofurandiol, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 7-Hydroxy-6-methoxy-alpha-pyrufuran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 7-hydroxy-6-methoxy-alpha-pyrufuran has been detected, but not quantified in, fruits. This could make 7-hydroxy-6-methoxy-alpha-pyrufuran a potential biomarker for the consumption of these foods.

Structure

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

HMDB0041295
     RDKit          3D
7-Hydroxy-6-methoxy-alpha-pyrufuran
 39 41  0  0  0  0  0  0  0  0999 V2000
   -4.6107    1.6122    1.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    1.0595    0.3420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.4878    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136   -0.8525    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099   -1.6668    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347   -1.3922    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474   -2.7432    0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -3.6811   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -0.6184    0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    0.7406    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096    1.2609   -0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    0.3614    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    0.3930    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8851    1.5865   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612    1.9917   -1.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -0.7231    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4317   -0.6476    0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -1.9173    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139   -1.9628    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -0.8394    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    1.2609    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    2.6038   -0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393    3.0294   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1001    2.5823    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3269    0.8592    1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636    1.7847    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539   -1.3595    0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -4.5099    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -3.2153   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -4.0566   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    1.1443   -2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1484    2.4940   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154    2.7593   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9562   -1.5001    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.8232    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -2.9079    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    4.0789   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    2.4112   -2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    2.9151   -1.7008 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 10 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 20  9  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END


  Mrv0541 05061312332D          

 23 25  0  0  0  0            999 V2000
    4.4703   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723    2.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6024   -1.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    1.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
 21  3  1  0  0  0  0
 21 15  1  0  0  0  0
 22  4  1  0  0  0  0
 22 16  1  0  0  0  0
 23 11  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041295

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OC3=C(C=CC(O)=C3OC)C2=C(OC)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c1-19-12-8(17)6-5-7-9-13(20-2)10(18)15(21-3)16(22-4)14(9)23-11(7)12/h5-6,17-18H,1-4H3

> <INCHI_KEY>
QPJPNKHHNVCLCF-UHFFFAOYSA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.294

> <EXACT_MASS>
320.089602866

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.941292052876737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,6,10-tetramethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaene-4,11-diol

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.9134313910000003

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.7771164719166

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.138021635218989

> <JCHEM_PKA_STRONGEST_BASIC>
-3.494960404290674

> <JCHEM_POLAR_SURFACE_AREA>
90.52000000000001

> <JCHEM_REFRACTIVITY>
81.04140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,6,10-tetramethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaene-4,11-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041295
     RDKit          3D
7-Hydroxy-6-methoxy-alpha-pyrufuran
 39 41  0  0  0  0  0  0  0  0999 V2000
   -4.6107    1.6122    1.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    1.0595    0.3420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.4878    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136   -0.8525    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099   -1.6668    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347   -1.3922    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474   -2.7432    0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -3.6811   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -0.6184    0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    0.7406    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096    1.2609   -0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    0.3614    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    0.3930    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8851    1.5865   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612    1.9917   -1.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -0.7231    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4317   -0.6476    0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -1.9173    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139   -1.9628    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -0.8394    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    1.2609    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    2.6038   -0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393    3.0294   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1001    2.5823    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3269    0.8592    1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636    1.7847    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539   -1.3595    0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -4.5099    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -3.2153   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -4.0566   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    1.1443   -2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1484    2.4940   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154    2.7593   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9562   -1.5001    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.8232    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -2.9079    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    4.0789   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    2.4112   -2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    2.9151   -1.7008 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 10 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 20  9  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  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       8.345  -2.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.255   4.844   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.155  -1.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.124  -2.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.899   0.130   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.727   3.059   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.838  -2.159   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.382  -2.159   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.610  -1.280   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9   11                                                  
CONECT    8    6   12   17                                                  
CONECT    9    7   13   14                                                  
CONECT   10   13   15   18                                                  
CONECT   11    7   12   23                                                  
CONECT   12    8   11   19                                                  
CONECT   13    9   10   20                                                  
CONECT   14    9   16   23                                                  
CONECT   15   10   16   21                                                  
CONECT   16   14   15   22                                                  
CONECT   17    8                                                            
CONECT   18   10                                                            
CONECT   19    1   12                                                       
CONECT   20    2   13                                                       
CONECT   21    3   15                                                       
CONECT   22    4   16                                                       
CONECT   23   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0041295
HETATM    1  C1  UNL     1      -4.611   1.612   1.446  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.965   1.060   0.342  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.690   0.488   0.380  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.514  -0.853   0.644  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.610  -1.667   0.880  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.235  -1.392   0.675  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.047  -2.743   0.940  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.044  -3.681  -0.145  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.117  -0.618   0.446  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.286   0.741   0.177  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.910   1.261  -0.004  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.853   0.361   0.123  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.241   0.393   0.030  1.00  0.00           C  
HETATM   14  O5  UNL     1       3.885   1.586  -0.256  1.00  0.00           O  
HETATM   15  C10 UNL     1       4.161   1.992  -1.573  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.027  -0.723   0.212  1.00  0.00           C  
HETATM   17  O6  UNL     1       5.432  -0.648   0.110  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.401  -1.917   0.497  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.014  -1.963   0.592  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.240  -0.839   0.408  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.573   1.261   0.151  1.00  0.00           C  
HETATM   22  O7  UNL     1      -1.766   2.604  -0.113  1.00  0.00           O  
HETATM   23  C16 UNL     1      -1.939   3.029  -1.470  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.100   2.582   1.211  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.327   0.859   1.839  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.864   1.785   2.249  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.554  -1.359   0.876  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.376  -4.510   0.183  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.613  -3.215  -1.067  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.063  -4.057  -0.340  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.111   1.144  -2.258  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.148   2.494  -1.560  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.415   2.759  -1.858  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.956  -1.500   0.253  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.984  -2.823   0.648  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.546  -2.908   0.819  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.633   4.079  -1.614  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.361   2.411  -2.170  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.039   2.915  -1.701  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5    6
CONECT    5   27
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   28   29   30
CONECT    9   10   20
CONECT   10   11   21   21
CONECT   11   12
CONECT   12   13   13   20
CONECT   13   14   16
CONECT   14   15
CONECT   15   31   32   33
CONECT   16   17   18   18
CONECT   17   34
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   21   22
CONECT   22   23
CONECT   23   37   38   39
END

HMDB0041295
     RDKit          3D
7-Hydroxy-6-methoxy-alpha-pyrufuran
 39 41  0  0  0  0  0  0  0  0999 V2000
   -4.6107    1.6122    1.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9646    1.0595    0.3420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    0.4878    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136   -0.8525    0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6099   -1.6668    0.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347   -1.3922    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474   -2.7432    0.9402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -3.6811   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172   -0.6184    0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    0.7406    0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096    1.2609   -0.0041 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532    0.3614    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    0.3930    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8851    1.5865   -0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612    1.9917   -1.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0273   -0.7231    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4317   -0.6476    0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4009   -1.9173    0.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139   -1.9628    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400   -0.8394    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    1.2609    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    2.6038   -0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9393    3.0294   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1001    2.5823    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3269    0.8592    1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8636    1.7847    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5539   -1.3595    0.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757   -4.5099    0.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -3.2153   -1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -4.0566   -0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    1.1443   -2.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1484    2.4940   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154    2.7593   -1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9562   -1.5001    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843   -2.8232    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -2.9079    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    4.0789   -1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3606    2.4112   -2.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    2.9151   -1.7008 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  6  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 10 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 20  9  1  0
 20 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-6-methoxy-a-pyrufuran	Generator
7-Hydroxy-6-methoxy-α-pyrufuran	Generator
1,3,4,6-Tetramethoxy-2,7-dibenzofurandiol	HMDB
2,7-Dihydroxy-1,3,4,6-tetramethoxydibenzofuran	HMDB

Chemical Formula

C₁₆H₁₆O₇

Average Molecular Weight

320.294

Monoisotopic Molecular Weight

320.089602866

IUPAC Name

3,5,6,10-tetramethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaene-4,11-diol

Traditional Name

3,5,6,10-tetramethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),2,4,6,10,12-hexaene-4,11-diol

CAS Registry Number

167278-45-7

SMILES

COC1=C2OC3=C(C=CC(O)=C3OC)C2=C(OC)C(O)=C1OC

InChI Identifier

InChI=1S/C16H16O7/c1-19-12-8(17)6-5-7-9-13(20-2)10(18)15(21-3)16(22-4)14(9)23-11(7)12/h5-6,17-18H,1-4H3

InChI Key

QPJPNKHHNVCLCF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041295)
Cytoplasm (HMDB: HMDB0041295)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041295)

Source

Exogenous

Food

Food (HMDB: HMDB0041295)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041295)

Not Available

Nutrient (HMDB: HMDB0041295)

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
Water Solubility	0.46 g/L	ALOGPS
logP	1.72	ALOGPS
logP	1.91	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.14	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.04 m³·mol⁻¹	ChemAxon
Polarizability	31.94 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]+	173.906	31661259
DarkChem	[M-H]-	173.867	31661259
DeepCCS	[M+H]+	172.971	30932474
DeepCCS	[M-H]-	170.613	30932474
DeepCCS	[M-2H]-	204.099	30932474
DeepCCS	[M+Na]+	179.325	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.4	32859911
AllCCS	[M+NH4]+	174.9	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	175.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-6-methoxy-alpha-pyrufuran	COC1=C2OC3=C(C=CC(O)=C3OC)C2=C(OC)C(O)=C1OC	4701.7	Standard polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran	COC1=C2OC3=C(C=CC(O)=C3OC)C2=C(OC)C(O)=C1OC	2652.8	Standard non polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran	COC1=C2OC3=C(C=CC(O)=C3OC)C2=C(OC)C(O)=C1OC	2642.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-6-methoxy-alpha-pyrufuran,1TMS,isomer #1	COC1=C(O)C(OC)=C2C(=C1OC)OC1=C(OC)C(O[Si](C)(C)C)=CC=C12	2758.3	Semi standard non polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran,1TMS,isomer #2	COC1=C(O[Si](C)(C)C)C(OC)=C2C(=C1OC)OC1=C(OC)C(O)=CC=C12	2764.7	Semi standard non polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(OC)=C2C(=C1OC)OC1=C(OC)C(O[Si](C)(C)C)=CC=C12	2734.8	Semi standard non polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran,1TBDMS,isomer #1	COC1=C(O)C(OC)=C2C(=C1OC)OC1=C(OC)C(O[Si](C)(C)C(C)(C)C)=CC=C12	2992.3	Semi standard non polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran,1TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2C(=C1OC)OC1=C(OC)C(O)=CC=C12	2966.8	Semi standard non polar	33892256
7-Hydroxy-6-methoxy-alpha-pyrufuran,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2C(=C1OC)OC1=C(OC)C(O[Si](C)(C)C(C)(C)C)=CC=C12	3121.3	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 - 7-Hydroxy-6-methoxy-alpha-pyrufuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0194000000-9ba20137e7b5095d9bab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran GC-MS (2 TMS) - 70eV, Positive	splash10-006t-1006900000-56ee8938079bb7219eb9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 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 - 7-Hydroxy-6-methoxy-alpha-pyrufuran 10V, Positive-QTOF	splash10-00di-0009000000-493018de3b0f15426c01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 20V, Positive-QTOF	splash10-00di-0049000000-674cafab97d109156dbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 40V, Positive-QTOF	splash10-00bj-1090000000-9a116b88a5bbef9d23a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 10V, Negative-QTOF	splash10-014i-0009000000-f028ef986752ef7cc600	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 20V, Negative-QTOF	splash10-014i-0029000000-0805c10db826f7064044	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 40V, Negative-QTOF	splash10-059i-2890000000-b93749c6a8bbadfe0e9b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 10V, Negative-QTOF	splash10-014i-0009000000-1b5d680c4b7d05223f19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 20V, Negative-QTOF	splash10-014i-0029000000-337cd115cb56324e90f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 40V, Negative-QTOF	splash10-05cs-1090000000-a90d58722b63bcac1460	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 10V, Positive-QTOF	splash10-00di-0009000000-95ba69cab2452329bc77	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 20V, Positive-QTOF	splash10-00di-0009000000-95ba69cab2452329bc77	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-6-methoxy-alpha-pyrufuran 40V, Positive-QTOF	splash10-0a4i-0390000000-870320f2335648130fa3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021212

KNApSAcK ID

Not Available

Chemspider ID

8579144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10403706

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

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

Showing metabocard for 7-Hydroxy-6-methoxy-alpha-pyrufuran (HMDB0041295)

MOL for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

3D MOL for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

3D SDF for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

3D-SDF for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

PDB for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

3D PDB for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

SMILES for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

INCHI for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

Structure for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

3D Structure for HMDB0041295 (7-Hydroxy-6-methoxy-alpha-pyrufuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra