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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:58 UTC

Update Date

2022-03-07 02:52:26 UTC

HMDB ID

HMDB0030131

Secondary Accession Numbers

HMDB30131

Metabolite Identification

Common Name

gamma-Pyrufuran

Description

gamma-Pyrufuran, also known as γ-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. gamma-Pyrufuran is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, gamma-pyrufuran has been detected, but not quantified in, pomes. This could make gamma-pyrufuran a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030131
     RDKit          3D
gamma-Pyrufuran
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.6062    0.1807    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6358   -0.2304   -0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794   -0.2866   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275   -1.4089    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -2.5399    0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2673   -1.4116    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -2.5330    0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -3.6156    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -0.2815   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.8683   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    1.7831   -0.7088 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368    1.3120   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1885    1.8757   -0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736    1.1490    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.6934    0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319   -0.1484    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828   -0.7214    0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    0.0002    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    0.8284   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581    1.9496   -1.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000    2.9855   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0967    0.6885    1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246   -0.6373    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114    0.8764   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767   -3.3480    0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433   -3.9811    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -3.2282   -0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1303   -4.4201   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    2.8935   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    2.1852    0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.6951    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780   -1.7256    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080    2.9002   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316    3.9382   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249    3.1049    0.5162 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
 14 16  2  0
 16 17  1  0
 17 18  2  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 18  9  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv0541 02241214412D          

 21 23  0  0  0  0            999 V2000
   -1.7734   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1134   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    0.4946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234    0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416    1.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7834    1.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609   -0.9897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -0.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1134   -1.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159   -1.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    1.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909    1.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    1.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509    0.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030131

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OC3=CC(O)=CC=C3C2=C(OC)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-18-12-10-8-5-4-7(16)6-9(8)21-13(10)15(20-3)14(19-2)11(12)17/h4-6,16-17H,1-3H3

> <INCHI_KEY>
KHGAPBYQBHBCBX-UHFFFAOYSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.218268044019005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,6-trimethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene-4,11-diol

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.0711026566666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.24213596159394

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.722734926917791

> <JCHEM_PKA_STRONGEST_BASIC>
-3.180096220987321

> <JCHEM_POLAR_SURFACE_AREA>
81.29

> <JCHEM_REFRACTIVITY>
74.57820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,6-trimethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene-4,11-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030131
     RDKit          3D
gamma-Pyrufuran
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.6062    0.1807    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6358   -0.2304   -0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794   -0.2866   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275   -1.4089    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -2.5399    0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2673   -1.4116    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -2.5330    0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -3.6156    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -0.2815   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.8683   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    1.7831   -0.7088 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368    1.3120   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1885    1.8757   -0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736    1.1490    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.6934    0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319   -0.1484    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828   -0.7214    0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    0.0002    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    0.8284   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581    1.9496   -1.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000    2.9855   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0967    0.6885    1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246   -0.6373    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114    0.8764   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767   -3.3480    0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433   -3.9811    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -3.2282   -0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1303   -4.4201   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    2.8935   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    2.1852    0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.6951    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780   -1.7256    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080    2.9002   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316    3.9382   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249    3.1049    0.5162 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
 14 16  2  0
 16 17  1  0
 17 18  2  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 18  9  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.310  -1.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.078  -0.615   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.770   0.923   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.230   1.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.692   2.309   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.078   3.695   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.462   3.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.234  -1.847   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.540  -1.847   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.924  -0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.384  -0.307   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.692  -1.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.692  -2.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.078  -3.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.310  -2.925   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.696  -3.695   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.696   3.387   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.156   3.387   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.232   2.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.848   0.769   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.388   0.615   0.000  0.00  0.00           O+0
CONECT    1    2   15                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11    4   10   12                                                  
CONECT   12    2   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15    1   14   16                                                  
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18   17   19                                                       
CONECT   19    5   18   20                                                  
CONECT   20   10   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030131
HETATM    1  C1  UNL     1      -4.606   0.181   0.205  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.636  -0.230  -0.706  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.279  -0.287  -0.465  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.627  -1.409   0.044  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.351  -2.540   0.332  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.267  -1.412   0.267  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.314  -2.533   0.763  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.826  -3.616   0.038  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.462  -0.282  -0.019  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.158   0.868  -0.532  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.767   1.783  -0.709  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.937   1.312  -0.347  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.188   1.876  -0.343  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.274   1.149   0.097  1.00  0.00           C  
HETATM   15  O5  UNL     1       5.565   1.693   0.114  1.00  0.00           O  
HETATM   16  C11 UNL     1       4.132  -0.148   0.540  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.883  -0.721   0.539  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.818   0.000   0.104  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.528   0.828  -0.742  1.00  0.00           C  
HETATM   20  O6  UNL     1      -2.158   1.950  -1.247  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.700   2.985  -0.488  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.097   0.688   1.065  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.225  -0.637   0.609  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.311   0.876  -0.320  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.877  -3.348   0.700  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.743  -3.981   0.583  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.221  -3.228  -0.938  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.130  -4.420  -0.162  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.375   2.893  -0.678  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.951   2.185   0.889  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.022  -0.695   0.883  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.778  -1.726   0.887  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.808   2.900  -0.411  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.532   3.938  -1.070  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.225   3.105   0.516  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   26   27   28
CONECT    9   10   18
CONECT   10   11   19   19
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   16   16
CONECT   15   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   19   20
CONECT   20   21
CONECT   21   33   34   35
END

HMDB0030131
     RDKit          3D
gamma-Pyrufuran
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.6062    0.1807    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6358   -0.2304   -0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794   -0.2866   -0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6275   -1.4089    0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3514   -2.5399    0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2673   -1.4116    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -2.5330    0.7635 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8260   -3.6156    0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4619   -0.2815   -0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.8683   -0.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667    1.7831   -0.7088 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9368    1.3120   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1885    1.8757   -0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736    1.1490    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652    1.6934    0.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1319   -0.1484    0.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8828   -0.7214    0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    0.0002    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278    0.8284   -0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581    1.9496   -1.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000    2.9855   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0967    0.6885    1.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2246   -0.6373    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3114    0.8764   -0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767   -3.3480    0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7433   -3.9811    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -3.2282   -0.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1303   -4.4201   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    2.8935   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    2.1852    0.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223   -0.6951    0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780   -1.7256    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080    2.9002   -0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316    3.9382   -1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249    3.1049    0.5162 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
 14 16  2  0
 16 17  1  0
 17 18  2  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 19  3  1  0
 18  9  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-Pyrufuran	Generator
Γ-pyrufuran	Generator
1,3,4-Trimethoxydibenzofuran-2,7-diol	HMDB
2,7-Dihydroxy-1,3,4-trimethoxydibenzofuran	HMDB

Chemical Formula

C₁₅H₁₄O₆

Average Molecular Weight

290.2681

Monoisotopic Molecular Weight

290.07903818

IUPAC Name

3,5,6-trimethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene-4,11-diol

Traditional Name

3,5,6-trimethoxy-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(13),2,4,6,9,11-hexaene-4,11-diol

CAS Registry Number

93973-18-3

SMILES

COC1=C2OC3=CC(O)=CC=C3C2=C(OC)C(O)=C1OC

InChI Identifier

InChI=1S/C15H14O6/c1-18-12-10-8-5-4-7(16)6-9(8)21-13(10)15(20-3)14(19-2)11(12)17/h4-6,16-17H,1-3H3

InChI Key

KHGAPBYQBHBCBX-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

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: HMDB0030131)
Cytoplasm (HMDB: HMDB0030131)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030131)

Source

Endogenous

Endogenous (HMDB: HMDB0030131)

Plant

Plant (HMDB: HMDB0030131)

Exogenous

Food

Food (HMDB: HMDB0030131)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	2.14	ALOGPS
logP	2.07	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.58 m³·mol⁻¹	ChemAxon
Polarizability	29.22 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]+	167.264	31661259
DarkChem	[M-H]-	167.128	31661259
DeepCCS	[M+H]+	166.538	30932474
DeepCCS	[M-H]-	164.18	30932474
DeepCCS	[M-2H]-	197.067	30932474
DeepCCS	[M+Na]+	172.632	30932474
AllCCS	[M+H]+	164.7	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	168.0	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	168.2	32859911
AllCCS	[M+Na-2H]-	167.6	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Pyrufuran	COC1=C2OC3=CC(O)=CC=C3C2=C(OC)C(O)=C1OC	4474.3	Standard polar	33892256
gamma-Pyrufuran	COC1=C2OC3=CC(O)=CC=C3C2=C(OC)C(O)=C1OC	2583.8	Standard non polar	33892256
gamma-Pyrufuran	COC1=C2OC3=CC(O)=CC=C3C2=C(OC)C(O)=C1OC	2631.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Pyrufuran,1TMS,isomer #1	COC1=C(O)C(OC)=C2C(=C1OC)OC1=CC(O[Si](C)(C)C)=CC=C12	2687.2	Semi standard non polar	33892256
gamma-Pyrufuran,1TMS,isomer #2	COC1=C(O[Si](C)(C)C)C(OC)=C2C(=C1OC)OC1=CC(O)=CC=C12	2622.6	Semi standard non polar	33892256
gamma-Pyrufuran,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(OC)=C2C(=C1OC)OC1=CC(O[Si](C)(C)C)=CC=C12	2694.1	Semi standard non polar	33892256
gamma-Pyrufuran,1TBDMS,isomer #1	COC1=C(O)C(OC)=C2C(=C1OC)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C12	2922.8	Semi standard non polar	33892256
gamma-Pyrufuran,1TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2C(=C1OC)OC1=CC(O)=CC=C12	2846.3	Semi standard non polar	33892256
gamma-Pyrufuran,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2C(=C1OC)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C12	3103.1	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 - gamma-Pyrufuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-0090000000-e5c0e520a09b26c730a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Pyrufuran GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-3027900000-cdfda035a728a04720c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-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 - gamma-Pyrufuran 10V, Positive-QTOF	splash10-0006-0090000000-46fedc22d8d4a7060b31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 20V, Positive-QTOF	splash10-0006-0090000000-49d458a252ef8e15a41b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 40V, Positive-QTOF	splash10-002b-1090000000-399c5db40319dd121862	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 10V, Negative-QTOF	splash10-000i-0090000000-634ace74f3bbbba42f23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 20V, Negative-QTOF	splash10-000i-0090000000-f652d001c7700a6f0bb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 40V, Negative-QTOF	splash10-00di-4490000000-8c3842dfbd00ed5ea62a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 10V, Positive-QTOF	splash10-0006-0090000000-afe43bdc82c44950ba4a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 20V, Positive-QTOF	splash10-0006-0090000000-afe43bdc82c44950ba4a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 40V, Positive-QTOF	splash10-004r-1950000000-f7979623c85da0e99d1f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 10V, Negative-QTOF	splash10-000i-0090000000-2d980c515d025d58a6fa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 20V, Negative-QTOF	splash10-000i-0090000000-ddc3323ca742fb591752	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Pyrufuran 40V, Negative-QTOF	splash10-0udl-2490000000-42aeaa1ba87bfdb1b4d5	2021-09-25	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

FDB001935

KNApSAcK ID

Not Available

Chemspider ID

161099

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185310

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 gamma-Pyrufuran (HMDB0030131)

MOL for HMDB0030131 (gamma-Pyrufuran)

3D MOL for HMDB0030131 (gamma-Pyrufuran)

3D SDF for HMDB0030131 (gamma-Pyrufuran)

3D-SDF for HMDB0030131 (gamma-Pyrufuran)

PDB for HMDB0030131 (gamma-Pyrufuran)

3D PDB for HMDB0030131 (gamma-Pyrufuran)

SMILES for HMDB0030131 (gamma-Pyrufuran)

INCHI for HMDB0030131 (gamma-Pyrufuran)

Structure for HMDB0030131 (gamma-Pyrufuran)

3D Structure for HMDB0030131 (gamma-Pyrufuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra