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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:24:01 UTC

Update Date

2022-03-07 02:53:48 UTC

HMDB ID

HMDB0033649

Secondary Accession Numbers

HMDB33649

Metabolite Identification

Common Name

O-Demethylfonsecin

Description

O-Demethylfonsecin belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. O-Demethylfonsecin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on O-Demethylfonsecin.

Structure

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

HMDB0033649
     RDKit          3D
O-Demethylfonsecin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8782    1.7014   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    0.6875    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7870    0.4491    1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076   -0.6418   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -1.3938    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -2.5506    0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.7002    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    0.6585    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481    1.3835    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    0.7089    0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9180    1.4535    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.8178    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216    1.5386    0.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1871   -0.5383    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -1.3154    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589   -2.6514   -0.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7994   -0.6453    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -1.3657    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -2.7128   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    1.2774    0.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    2.7340   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9287    1.6840   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.4825   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5523   -0.1543    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -1.1695   -0.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488   -0.4506   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281    2.4656    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.5098    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    2.5282    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1275   -1.0803    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -3.3677   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -3.3427   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  1  0
 20  2  1  0
 18  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 19 32  1  0
M  END

  Mrv0541 05061307152D          

 20 22  0  0  0  0            999 V2000
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  2  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  3  2  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14  1  1  0  0  0  0
 14  5  1  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033649

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O6/c1-14(19)5-9(17)12-10(20-14)3-6-2-7(15)4-8(16)11(6)13(12)18/h2-4,15-16,18-19H,5H2,1H3

> <INCHI_KEY>
RTYDQIKVNMHQMZ-UHFFFAOYSA-N

> <FORMULA>
C14H12O6

> <MOLECULAR_WEIGHT>
276.2415

> <EXACT_MASS>
276.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.588924558843736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,6,8-tetrahydroxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.9241834036666663

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.484087610633718

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.248062678731293

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1586221081855905

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
69.50890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,6,8-tetrahydroxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033649
     RDKit          3D
O-Demethylfonsecin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8782    1.7014   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    0.6875    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7870    0.4491    1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076   -0.6418   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -1.3938    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -2.5506    0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.7002    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    0.6585    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481    1.3835    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    0.7089    0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9180    1.4535    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.8178    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216    1.5386    0.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1871   -0.5383    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -1.3154    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589   -2.6514   -0.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7994   -0.6453    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -1.3657    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -2.7128   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    1.2774    0.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    2.7340   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9287    1.6840   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.4825   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5523   -0.1543    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -1.1695   -0.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488   -0.4506   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281    2.4656    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.5098    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    2.5282    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1275   -1.0803    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -3.3677   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -3.3427   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  1  0
 20  2  1  0
 18  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 19 32  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      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.517   1.273   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    6    7                                                       
CONECT    3    6   10                                                       
CONECT    4    7    8                                                       
CONECT    5    9   14                                                       
CONECT    6    2    3   11                                                  
CONECT    7    2    4   15                                                  
CONECT    8    4   11   16                                                  
CONECT    9    5   12   17                                                  
CONECT   10    3   12   20                                                  
CONECT   11    6    8   13                                                  
CONECT   12    9   10   13                                                  
CONECT   13   11   12   18                                                  
CONECT   14    1    5   19   20                                             
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033649
HETATM    1  C1  UNL     1      -3.878   1.701  -0.677  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.093   0.688   0.149  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.787   0.449   1.359  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.008  -0.642  -0.552  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.889  -1.394   0.063  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.942  -2.551   0.514  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.591  -0.700   0.148  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.618   0.658   0.336  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.548   1.384   0.429  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.758   0.709   0.330  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.918   1.453   0.430  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.126   0.818   0.339  1.00  0.00           C  
HETATM   13  O3  UNL     1       5.322   1.539   0.436  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.187  -0.538   0.152  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.014  -1.315   0.048  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.159  -2.651  -0.136  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.799  -0.645   0.143  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.599  -1.366   0.049  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.607  -2.713  -0.141  1.00  0.00           O  
HETATM   20  O6  UNL     1      -1.848   1.277   0.430  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.507   2.734  -0.529  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.929   1.684  -0.304  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.823   1.482  -1.762  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.552  -0.154   1.103  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.981  -1.170  -0.373  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.849  -0.451  -1.630  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.528   2.466   0.579  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.858   2.510   0.576  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.276   2.528   0.572  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.127  -1.080   0.075  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.568  -3.368  -0.233  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.101  -3.343  -0.243  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4   20
CONECT    3   24
CONECT    4    5   25   26
CONECT    5    6    6    7
CONECT    7    8    8   18
CONECT    8    9   20
CONECT    9   10   10   27
CONECT   10   11   17
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18
CONECT   18   19
CONECT   19   32
END

HMDB0033649
     RDKit          3D
O-Demethylfonsecin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8782    1.7014   -0.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0932    0.6875    0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7870    0.4491    1.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0076   -0.6418   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -1.3938    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -2.5506    0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5911   -0.7002    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6176    0.6585    0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481    1.3835    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    0.7089    0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9180    1.4535    0.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.8178    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3216    1.5386    0.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1871   -0.5383    0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -1.3154    0.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589   -2.6514   -0.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7994   -0.6453    0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5991   -1.3657    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6075   -2.7128   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    1.2774    0.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    2.7340   -0.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9287    1.6840   -0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.4825   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5523   -0.1543    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9806   -1.1695   -0.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488   -0.4506   -1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281    2.4656    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.5098    0.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    2.5282    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1275   -1.0803    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -3.3677   -0.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1011   -3.3427   -0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  8 20  1  0
 20  2  1  0
 18  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Demethylfonsecin	ChEBI
Desmethylfonsecin	ChEBI
De-O-methylfonsecin	HMDB
YWA 1	HMDB
O-Demethylfonsecin	ChEBI

Chemical Formula

C₁₄H₁₂O₆

Average Molecular Weight

276.2415

Monoisotopic Molecular Weight

276.063388116

IUPAC Name

2,5,6,8-tetrahydroxy-2-methyl-2H,3H,4H-naphtho[2,3-b]pyran-4-one

Traditional Name

2,5,6,8-tetrahydroxy-2-methyl-3H-naphtho[2,3-b]pyran-4-one

CAS Registry Number

Not Available

SMILES

CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1

InChI Identifier

InChI=1S/C14H12O6/c1-14(19)5-9(17)12-10(20-14)3-6-2-7(15)4-8(16)11(6)13(12)18/h2-4,15-16,18-19H,5H2,1H3

InChI Key

RTYDQIKVNMHQMZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Benzochromone
Naphthopyranone
Chromone
2-naphthol
1-naphthol
Chromane
Benzopyran
Naphthalene
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Vinylogous acid
Ketone
Hemiacetal
Polyol
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033649)
Cytoplasm (HMDB: HMDB0033649)

Source

Exogenous

Exogenous (HMDB: HMDB0033649)

Food

Food (HMDB: HMDB0033649)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033649)

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	0.79 g/L	ALOGPS
logP	0.93	ALOGPS
logP	1.92	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.51 m³·mol⁻¹	ChemAxon
Polarizability	26.59 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]+	164.076	31661259
DarkChem	[M-H]-	164.099	31661259
DeepCCS	[M+H]+	166.159	30932474
DeepCCS	[M-H]-	163.801	30932474
DeepCCS	[M-2H]-	196.687	30932474
DeepCCS	[M+Na]+	172.253	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.6	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Demethylfonsecin	CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1	4273.3	Standard polar	33892256
O-Demethylfonsecin	CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1	2705.3	Standard non polar	33892256
O-Demethylfonsecin	CC1(O)CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1	2834.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Demethylfonsecin,1TMS,isomer #1	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O)O1	2628.8	Semi standard non polar	33892256
O-Demethylfonsecin,1TMS,isomer #2	CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C)O1	2610.8	Semi standard non polar	33892256
O-Demethylfonsecin,1TMS,isomer #3	CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O)O1	2607.8	Semi standard non polar	33892256
O-Demethylfonsecin,1TMS,isomer #4	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O)O1	2655.9	Semi standard non polar	33892256
O-Demethylfonsecin,2TMS,isomer #1	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O)O1	2606.7	Semi standard non polar	33892256
O-Demethylfonsecin,2TMS,isomer #2	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O)O1	2596.8	Semi standard non polar	33892256
O-Demethylfonsecin,2TMS,isomer #3	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C)O1	2624.1	Semi standard non polar	33892256
O-Demethylfonsecin,2TMS,isomer #4	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O[Si](C)(C)C)O1	2598.2	Semi standard non polar	33892256
O-Demethylfonsecin,2TMS,isomer #5	CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O1	2585.0	Semi standard non polar	33892256
O-Demethylfonsecin,2TMS,isomer #6	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O)O1	2649.5	Semi standard non polar	33892256
O-Demethylfonsecin,3TMS,isomer #1	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O)O1	2624.3	Semi standard non polar	33892256
O-Demethylfonsecin,3TMS,isomer #2	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O)C3=C2O[Si](C)(C)C)O1	2606.7	Semi standard non polar	33892256
O-Demethylfonsecin,3TMS,isomer #3	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O1	2609.5	Semi standard non polar	33892256
O-Demethylfonsecin,3TMS,isomer #4	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O1	2643.9	Semi standard non polar	33892256
O-Demethylfonsecin,4TMS,isomer #1	CC1(O[Si](C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C3=C2O[Si](C)(C)C)O1	2687.8	Semi standard non polar	33892256
O-Demethylfonsecin,1TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O)O1	2900.6	Semi standard non polar	33892256
O-Demethylfonsecin,1TBDMS,isomer #2	CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O1	2882.4	Semi standard non polar	33892256
O-Demethylfonsecin,1TBDMS,isomer #3	CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O1	2864.1	Semi standard non polar	33892256
O-Demethylfonsecin,1TBDMS,isomer #4	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O)O1	2907.6	Semi standard non polar	33892256
O-Demethylfonsecin,2TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O)O1	3118.4	Semi standard non polar	33892256
O-Demethylfonsecin,2TBDMS,isomer #2	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O1	3081.8	Semi standard non polar	33892256
O-Demethylfonsecin,2TBDMS,isomer #3	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O1	3112.2	Semi standard non polar	33892256
O-Demethylfonsecin,2TBDMS,isomer #4	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O1	3105.7	Semi standard non polar	33892256
O-Demethylfonsecin,2TBDMS,isomer #5	CC1(O)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O1	3065.7	Semi standard non polar	33892256
O-Demethylfonsecin,2TBDMS,isomer #6	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O1	3139.1	Semi standard non polar	33892256
O-Demethylfonsecin,3TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O)O1	3341.8	Semi standard non polar	33892256
O-Demethylfonsecin,3TBDMS,isomer #2	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O)C3=C2O[Si](C)(C)C(C)(C)C)O1	3309.7	Semi standard non polar	33892256
O-Demethylfonsecin,3TBDMS,isomer #3	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O1	3268.3	Semi standard non polar	33892256
O-Demethylfonsecin,3TBDMS,isomer #4	CC1(O)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O1	3320.8	Semi standard non polar	33892256
O-Demethylfonsecin,4TBDMS,isomer #1	CC1(O[Si](C)(C)C(C)(C)C)CC(=O)C2=C(C=C3C=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C3=C2O[Si](C)(C)C(C)(C)C)O1	3524.2	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 - O-Demethylfonsecin GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-2190000000-92067630613a090a6268	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylfonsecin GC-MS (4 TMS) - 70eV, Positive	splash10-00rg-9100740000-883c543f5e40f4da387c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Demethylfonsecin 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 - O-Demethylfonsecin 10V, Positive-QTOF	splash10-056r-0090000000-d4ed37b50af2d0f4561c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Positive-QTOF	splash10-0a6r-1090000000-57b3333d9a3ed9489239	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Positive-QTOF	splash10-0gdi-1890000000-95593eff745cf0e03969	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Negative-QTOF	splash10-004i-0390000000-e0861a6bb40d34035f29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Negative-QTOF	splash10-056r-0490000000-745be75b0f78defaf226	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Negative-QTOF	splash10-00xr-1930000000-85766bd5d383df5fa4af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Negative-QTOF	splash10-004i-0090000000-fdefbfcb4d27fe320d4b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Negative-QTOF	splash10-004i-0090000000-34fc5131036b1ec5e26f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Negative-QTOF	splash10-0aou-3290000000-3468e25876a93af9e730	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 10V, Positive-QTOF	splash10-004i-0090000000-9f46e36098b5d5b4738d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 20V, Positive-QTOF	splash10-056r-0090000000-f42f9726e3904deb0d4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Demethylfonsecin 40V, Positive-QTOF	splash10-05mo-5290000000-38b1ad796f7ab2088653	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	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

FDB011751

KNApSAcK ID

Not Available

Chemspider ID

35013649

KEGG Compound ID

Not Available

BioCyc ID

CPD-18255

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100923872

PDB ID

Not Available

ChEBI ID

133763

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 O-Demethylfonsecin (HMDB0033649)

MOL for HMDB0033649 (O-Demethylfonsecin)

3D MOL for HMDB0033649 (O-Demethylfonsecin)

3D SDF for HMDB0033649 (O-Demethylfonsecin)

3D-SDF for HMDB0033649 (O-Demethylfonsecin)

PDB for HMDB0033649 (O-Demethylfonsecin)

3D PDB for HMDB0033649 (O-Demethylfonsecin)

SMILES for HMDB0033649 (O-Demethylfonsecin)

INCHI for HMDB0033649 (O-Demethylfonsecin)

Structure for HMDB0033649 (O-Demethylfonsecin)

3D Structure for HMDB0033649 (O-Demethylfonsecin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra