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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:57:52 UTC

Update Date

2022-03-07 02:56:57 UTC

HMDB ID

HMDB0041294

Secondary Accession Numbers

HMDB41294

Metabolite Identification

Common Name

6-Methoxy-alpha-pyrufuran

Description

6-Methoxy-alpha-pyrufuran belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring. 6-Methoxy-alpha-pyrufuran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6-methoxy-alpha-pyrufuran has been detected, but not quantified in, fruits and medlars. This could make 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

HMDB0041294
     RDKit          3D
6-Methoxy-alpha-pyrufuran
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.5349   -1.8443    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034   -0.9679   -0.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6261   -0.4905   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    0.6870    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    1.3389    0.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798    1.1555    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066    2.3350    1.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1592    3.6105    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1518    0.4658    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316   -0.7214   -0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839   -1.1721   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -0.3864   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.3890    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -1.4482   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3445   -1.4394   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463    0.6303    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    1.6647    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    1.6722    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    0.6578    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006   -1.1830   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120   -2.3769   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -2.3791   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211   -2.7049   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829   -1.3095    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.3033    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021    0.9607    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117    4.1617    1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8569    3.5357   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    4.1901    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7452   -1.6901    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -2.2064   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -0.4569   -0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366    0.6297    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    2.4738    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370    2.4501    1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137   -2.5203   -3.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0892   -1.4249   -3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -3.2046   -3.1154 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  2  0
 17 18  1  0
 18 19  2  0
 10 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  9  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061312332D          

 22 24  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
    3.7054    1.0256    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
    3.9604    0.2410    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
    3.4084   -0.3721    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
    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
   -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  2  0  0  0  0
 10  8  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18  1  1  0  0  0  0
 18  9  1  0  0  0  0
 19  2  1  0  0  0  0
 19 13  1  0  0  0  0
 20  3  1  0  0  0  0
 20 15  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 22 12  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041294

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C1OC1=C(OC)C(OC)=C(O)C(OC)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-18-9-7-5-6-8-10-13(19-2)11(17)15(20-3)16(21-4)14(10)22-12(8)9/h5-7,17H,1-4H3

> <INCHI_KEY>
ZUMWPOBUQWYISM-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.2946

> <EXACT_MASS>
304.094688244

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.055489373844388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <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-hexaen-4-ol

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.2169967126666665

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.034734632750533

> <JCHEM_PKA_STRONGEST_BASIC>
-3.68661508566071

> <JCHEM_POLAR_SURFACE_AREA>
70.29

> <JCHEM_REFRACTIVITY>
79.0605

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methoxy-α-pyrufuran

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041294
     RDKit          3D
6-Methoxy-alpha-pyrufuran
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.5349   -1.8443    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034   -0.9679   -0.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6261   -0.4905   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    0.6870    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    1.3389    0.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798    1.1555    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066    2.3350    1.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1592    3.6105    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1518    0.4658    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316   -0.7214   -0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839   -1.1721   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -0.3864   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.3890    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -1.4482   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3445   -1.4394   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463    0.6303    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    1.6647    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    1.6722    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    0.6578    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006   -1.1830   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120   -2.3769   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -2.3791   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211   -2.7049   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829   -1.3095    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.3033    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021    0.9607    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117    4.1617    1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8569    3.5357   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    4.1901    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7452   -1.6901    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -2.2064   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -0.4569   -0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366    0.6297    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    2.4738    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370    2.4501    1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137   -2.5203   -3.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0892   -1.4249   -3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -3.2046   -3.1154 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  2  0
 17 18  1  0
 18 19  2  0
 10 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  9  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  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       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856  -0.374   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      -0.727   3.059   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.838  -2.159   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.285   3.699   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.382  -2.159   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.610  -1.280   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10   12                                                  
CONECT    9    7   12   18                                                  
CONECT   10    8   13   14                                                  
CONECT   11   13   15   17                                                  
CONECT   12    8    9   22                                                  
CONECT   13   10   11   19                                                  
CONECT   14   10   16   22                                                  
CONECT   15   11   16   20                                                  
CONECT   16   14   15   21                                                  
CONECT   17   11                                                            
CONECT   18    1    9                                                       
CONECT   19    2   13                                                       
CONECT   20    3   15                                                       
CONECT   21    4   16                                                       
CONECT   22   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0041294
HETATM    1  C1  UNL     1      -4.535  -1.844   0.398  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.903  -0.968  -0.525  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.626  -0.490  -0.201  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.535   0.687   0.514  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.701   1.339   0.878  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.280   1.156   0.831  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.207   2.335   1.547  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.159   3.610   0.935  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.152   0.466   0.444  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.232  -0.721  -0.277  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.984  -1.172  -0.517  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.883  -0.386  -0.016  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.276  -0.389   0.022  1.00  0.00           C  
HETATM   14  O5  UNL     1       3.932  -1.448  -0.602  1.00  0.00           O  
HETATM   15  C10 UNL     1       5.344  -1.439  -0.557  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.946   0.630   0.659  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.283   1.665   1.269  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.902   1.672   1.234  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.217   0.658   0.599  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.501  -1.183  -0.591  1.00  0.00           C  
HETATM   21  O6  UNL     1      -1.612  -2.377  -1.317  1.00  0.00           O  
HETATM   22  C16 UNL     1      -1.643  -2.379  -2.743  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.021  -2.705  -0.131  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.283  -1.309   1.009  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.799  -2.303   1.088  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.602   0.961   0.625  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.112   4.162   1.041  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.857   3.536  -0.131  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.381   4.190   1.475  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.745  -1.690   0.445  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.685  -2.206  -1.300  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.739  -0.457  -0.890  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.037   0.630   0.690  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.827   2.474   1.775  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.337   2.450   1.695  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.614  -2.520  -3.166  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.089  -1.425  -3.094  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.294  -3.205  -3.115  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5    6
CONECT    5   26
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   27   28   29
CONECT    9   10   19
CONECT   10   11   20   20
CONECT   11   12
CONECT   12   13   13   19
CONECT   13   14   16
CONECT   14   15
CONECT   15   30   31   32
CONECT   16   17   17   33
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   20   21
CONECT   21   22
CONECT   22   36   37   38
END

HMDB0041294
     RDKit          3D
6-Methoxy-alpha-pyrufuran
 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.5349   -1.8443    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9034   -0.9679   -0.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6261   -0.4905   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349    0.6870    0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008    1.3389    0.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798    1.1555    0.8313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066    2.3350    1.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1592    3.6105    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1518    0.4658    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2316   -0.7214   -0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839   -1.1721   -0.5167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -0.3864   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2757   -0.3890    0.0220 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9321   -1.4482   -0.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3445   -1.4394   -0.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463    0.6303    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    1.6647    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    1.6722    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172    0.6578    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5006   -1.1830   -0.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6120   -2.3769   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -2.3791   -2.7429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0211   -2.7049   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2829   -1.3095    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7991   -2.3033    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021    0.9607    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117    4.1617    1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8569    3.5357   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3814    4.1901    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7452   -1.6901    0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -2.2064   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7391   -0.4569   -0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0366    0.6297    0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    2.4738    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370    2.4501    1.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137   -2.5203   -3.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0892   -1.4249   -3.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -3.2046   -3.1154 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  2  0
 17 18  1  0
 18 19  2  0
 10 20  2  0
 20 21  1  0
 21 22  1  0
 20  3  1  0
 19  9  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Methoxy-a-pyrufuran	Generator
6-Methoxy-α-pyrufuran	Generator
1,3,4,6-Tetramethoxy-2-dibenzofuranol	HMDB
2-Hydroxy-1,3,4,6-tetramethoxydibenzofuran	HMDB

Chemical Formula

C₁₆H₁₆O₆

Average Molecular Weight

304.2946

Monoisotopic Molecular Weight

304.094688244

IUPAC Name

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

Traditional Name

6-methoxy-α-pyrufuran

CAS Registry Number

167278-44-6

SMILES

COC1=CC=CC2=C1OC1=C(OC)C(OC)=C(O)C(OC)=C21

InChI Identifier

InChI=1S/C16H16O6/c1-18-9-7-5-6-8-10-13(19-2)11(17)15(20-3)16(21-4)14(10)22-12(8)9/h5-7,17H,1-4H3

InChI Key

ZUMWPOBUQWYISM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzofurans. Dibenzofurans are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Dibenzofurans

Direct Parent

Dibenzofurans

Alternative Parents

Substituents

Dibenzofuran
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzofurans (CHEBI:2209 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041294)

Cellular substructure

Membrane (HMDB: HMDB0041294)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041294)

Source

Exogenous

Food

Food (HMDB: HMDB0041294)

Fruit

Pome

Medlar (FooDB: FOOD00114)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041294)

Not Available

Nutrient (HMDB: HMDB0041294)

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	0.16 g/L	ALOGPS
logP	2.59	ALOGPS
logP	2.22	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.06 m³·mol⁻¹	ChemAxon
Polarizability	31.06 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]+	169.761	31661259
DarkChem	[M-H]-	169.539	31661259
DeepCCS	[M-2H]-	200.742	30932474
DeepCCS	[M+Na]+	176.307	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.3	32859911
AllCCS	[M+NH4]+	172.1	32859911
AllCCS	[M+Na]+	173.0	32859911
AllCCS	[M-H]-	173.9	32859911
AllCCS	[M+Na-2H]-	173.4	32859911
AllCCS	[M+HCOO]-	173.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methoxy-alpha-pyrufuran	COC1=CC=CC2=C1OC1=C(OC)C(OC)=C(O)C(OC)=C21	4157.7	Standard polar	33892256
6-Methoxy-alpha-pyrufuran	COC1=CC=CC2=C1OC1=C(OC)C(OC)=C(O)C(OC)=C21	2497.1	Standard non polar	33892256
6-Methoxy-alpha-pyrufuran	COC1=CC=CC2=C1OC1=C(OC)C(OC)=C(O)C(OC)=C21	2555.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Methoxy-alpha-pyrufuran,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(OC)=C2C(=C1OC)OC1=C(OC)C=CC=C12	2630.6	Semi standard non polar	33892256
6-Methoxy-alpha-pyrufuran,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2C(=C1OC)OC1=C(OC)C=CC=C12	2825.2	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 - 6-Methoxy-alpha-pyrufuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-022i-0191000000-e3758c86e73d41b05311	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Methoxy-alpha-pyrufuran GC-MS (1 TMS) - 70eV, Positive	splash10-03l0-1019000000-11c0eb8d57e455788e6e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 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 - 6-Methoxy-alpha-pyrufuran 10V, Positive-QTOF	splash10-0a4i-0019000000-7fc07a6d2472985e8ccb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 20V, Positive-QTOF	splash10-0a4i-0049000000-f0fcef7090aa07c681f4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 40V, Positive-QTOF	splash10-0ab9-2190000000-2ce2030670bde5054755	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 10V, Negative-QTOF	splash10-0udi-0009000000-125f8494bba0b7b95e44	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 20V, Negative-QTOF	splash10-0udi-0049000000-10ce157d43f467baf597	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 40V, Negative-QTOF	splash10-006t-4890000000-fd3324261428ab2335ab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 10V, Negative-QTOF	splash10-0udi-0009000000-04ccc09c7865adc86051	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 20V, Negative-QTOF	splash10-0uk9-0069000000-c8cde01f4d4d6d51d881	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 40V, Negative-QTOF	splash10-066u-1090000000-78e832e7208ad873e7f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 10V, Positive-QTOF	splash10-0a4i-0009000000-a392301a4f812f462a73	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 20V, Positive-QTOF	splash10-0a4i-0009000000-a392301a4f812f462a73	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Methoxy-alpha-pyrufuran 40V, Positive-QTOF	splash10-00l2-0490000000-09f2c15da19ab510ccc8	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441795

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 6-Methoxy-alpha-pyrufuran (HMDB0041294)

MOL for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

3D MOL for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

3D SDF for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

3D-SDF for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

PDB for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

3D PDB for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

SMILES for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

INCHI for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

Structure for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

3D Structure for HMDB0041294 (6-Methoxy-alpha-pyrufuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra