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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:55:13 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034124

Secondary Accession Numbers

HMDB34124

Metabolite Identification

Common Name

Fonsecin

Description

Fonsecin 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. Fonsecin 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 small amount of articles have been published on Fonsecin.

Structure

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

HMDB0034124
     RDKit          3D
Fonsecin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4193   -1.9821   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -1.6500   -0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088   -0.3231    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6821    0.6385   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    1.9791    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2293    2.9992    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    2.3013    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    1.3072    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189    1.6274    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976    0.6637    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9276   -0.6569    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.0179    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908   -2.3230    0.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741   -0.0272    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -1.6399    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246   -2.8020    0.8716 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -1.2451    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204    0.1283    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    0.7631   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    0.0416    2.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252    0.9895    0.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.3891   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5689   -3.0680   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9613   -1.6264    0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7405    0.4167   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9629    3.9604    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    3.3198    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    2.6674    0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -3.1737    0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152   -2.0015    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5246   -1.2096   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    0.2723   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    1.8503   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946    0.7030    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.4934    2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 14  3  1  0
 14  8  1  0
 21 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
M  END


  Mrv0541 05061307362D          

 21 23  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
    4.2868   -1.6500    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
    0.7145   -0.4125    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
    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
    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
    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
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11  4  2  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15  1  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034124

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-15(19)6-9(17)13-11(21-15)4-7-3-8(16)5-10(20-2)12(7)14(13)18/h3-5,16,18-19H,6H2,1-2H3

> <INCHI_KEY>
FKCYENFBFZUSDP-UHFFFAOYSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.559171936238045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
2.070077459666666

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.456539448581536

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.682731038730083

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158627340430351

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
73.9912

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034124
     RDKit          3D
Fonsecin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4193   -1.9821   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -1.6500   -0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088   -0.3231    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6821    0.6385   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    1.9791    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2293    2.9992    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    2.3013    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    1.3072    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189    1.6274    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976    0.6637    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9276   -0.6569    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.0179    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908   -2.3230    0.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741   -0.0272    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -1.6399    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246   -2.8020    0.8716 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -1.2451    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204    0.1283    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    0.7631   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    0.0416    2.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252    0.9895    0.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.3891   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5689   -3.0680   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9613   -1.6264    0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7405    0.4167   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9629    3.9604    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    3.3198    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    2.6674    0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -3.1737    0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152   -2.0015    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5246   -1.2096   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    0.2723   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    1.8503   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946    0.7030    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.4934    2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 14  3  1  0
 14  8  1  0
 21 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   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       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   20                                                            
CONECT    3    7    8                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    9   15                                                       
CONECT    7    3    4   12                                                  
CONECT    8    3    5   16                                                  
CONECT    9    6   13   17                                                  
CONECT   10    5   12   20                                                  
CONECT   11    4   13   21                                                  
CONECT   12    7   10   14                                                  
CONECT   13    9   11   14                                                  
CONECT   14   12   13   18                                                  
CONECT   15    1    6   19   21                                             
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    2   10                                                       
CONECT   21   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034124
HETATM    1  C1  UNL     1      -4.419  -1.982  -0.246  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.061  -1.650  -0.067  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.709  -0.323   0.048  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.682   0.638  -0.012  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.297   1.979   0.108  1.00  0.00           C  
HETATM    6  O2  UNL     1      -4.229   2.999   0.056  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.977   2.301   0.282  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.025   1.307   0.338  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.319   1.627   0.514  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.298   0.664   0.575  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.928  -0.657   0.458  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.390  -1.018   0.282  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.791  -2.323   0.161  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.374  -0.027   0.222  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.002  -1.640   0.535  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.725  -2.802   0.872  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.401  -1.245   0.214  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.720   0.128   0.758  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.820   0.763  -0.102  1.00  0.00           C  
HETATM   20  O5  UNL     1       4.164   0.042   2.097  1.00  0.00           O  
HETATM   21  O6  UNL     1       2.625   0.990   0.750  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.810  -1.389  -1.097  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.569  -3.068  -0.405  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.961  -1.626   0.677  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.741   0.417  -0.149  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.963   3.960   0.141  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.673   3.320   0.374  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.604   2.667   0.606  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.335  -3.174   0.160  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.115  -2.001   0.596  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.525  -1.210  -0.883  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.884   0.272  -1.081  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.639   1.850  -0.235  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.795   0.703   0.463  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.443  -0.493   2.554  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   27
CONECT    8    9    9   14
CONECT    9   10   28
CONECT   10   11   11   21
CONECT   11   12   15
CONECT   12   13   14   14
CONECT   13   29
CONECT   15   16   16   17
CONECT   17   18   30   31
CONECT   18   19   20   21
CONECT   19   32   33   34
CONECT   20   35
END

HMDB0034124
     RDKit          3D
Fonsecin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4193   -1.9821   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -1.6500   -0.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7088   -0.3231    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6821    0.6385   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970    1.9791    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2293    2.9992    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    2.3013    0.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245    1.3072    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189    1.6274    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2976    0.6637    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9276   -0.6569    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.0179    0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908   -2.3230    0.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741   -0.0272    0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0016   -1.6399    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246   -2.8020    0.8716 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -1.2451    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204    0.1283    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201    0.7631   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    0.0416    2.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6252    0.9895    0.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -1.3891   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5689   -3.0680   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9613   -1.6264    0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7405    0.4167   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9629    3.9604    0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730    3.3198    0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    2.6674    0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -3.1737    0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152   -2.0015    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5246   -1.2096   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8839    0.2723   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    1.8503   -0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7946    0.7030    0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4429   -0.4934    2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 14  3  1  0
 14  8  1  0
 21 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 17 30  1  0
 17 31  1  0
 19 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-dihydro-2,5,8-Trihydroxy-6-methoxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one, 9ci	HMDB
Antibiotic TMC 256b1	HMDB
O8-Demethylfonsecin b	HMDB
TMC 256b1	HMDB

Chemical Formula

C₁₅H₁₄O₆

Average Molecular Weight

290.2681

Monoisotopic Molecular Weight

290.07903818

IUPAC Name

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

Traditional Name

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

CAS Registry Number

3748-39-8

SMILES

COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1

InChI Identifier

InChI=1S/C15H14O6/c1-15(19)6-9(17)13-11(21-15)4-7-3-8(16)5-10(20-2)12(7)14(13)18/h3-5,16,18-19H,6H2,1-2H3

InChI Key

FKCYENFBFZUSDP-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

naphtho-gamma-pyrone (CHEBI:64543 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034124)
Cytoplasm (HMDB: HMDB0034124)

Source

Exogenous

Exogenous (HMDB: HMDB0034124)

Food

Food (HMDB: HMDB0034124)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034124)

Environmental role

Environmental contaminant (HMDB: HMDB0034124)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	198 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	1.6	ALOGPS
logP	2.07	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.99 m³·mol⁻¹	ChemAxon
Polarizability	28.56 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]+	169.281	31661259
DarkChem	[M-H]-	166.94	31661259
DeepCCS	[M+H]+	174.196	30932474
DeepCCS	[M-H]-	171.838	30932474
DeepCCS	[M-2H]-	204.724	30932474
DeepCCS	[M+Na]+	180.289	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.5	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.82 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3621 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2366.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	357.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	656.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	679.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1073.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	442.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1690.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	527.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	153.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fonsecin	COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1	4082.0	Standard polar	33892256
Fonsecin	COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1	2701.5	Standard non polar	33892256
Fonsecin	COC1=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=CC(O)=C1	2823.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fonsecin,1TMS,isomer #1	COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C)=C12	2576.2	Semi standard non polar	33892256
Fonsecin,1TMS,isomer #2	COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O)=C12	2571.2	Semi standard non polar	33892256
Fonsecin,1TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O)=C12	2682.3	Semi standard non polar	33892256
Fonsecin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C)=C12	2669.6	Semi standard non polar	33892256
Fonsecin,2TMS,isomer #2	COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O[Si](C)(C)C)=C12	2586.0	Semi standard non polar	33892256
Fonsecin,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O)=C12	2626.7	Semi standard non polar	33892256
Fonsecin,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C)O3)C(O[Si](C)(C)C)=C12	2664.3	Semi standard non polar	33892256
Fonsecin,1TBDMS,isomer #1	COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C(C)(C)C)=C12	2818.4	Semi standard non polar	33892256
Fonsecin,1TBDMS,isomer #2	COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O)=C12	2823.5	Semi standard non polar	33892256
Fonsecin,1TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O)=C12	2915.8	Semi standard non polar	33892256
Fonsecin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O)O3)C(O[Si](C)(C)C(C)(C)C)=C12	3121.2	Semi standard non polar	33892256
Fonsecin,2TBDMS,isomer #2	COC1=CC(O)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O[Si](C)(C)C(C)(C)C)=C12	3049.9	Semi standard non polar	33892256
Fonsecin,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O)=C12	3104.8	Semi standard non polar	33892256
Fonsecin,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC2=CC3=C(C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)O3)C(O[Si](C)(C)C(C)(C)C)=C12	3315.4	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 - Fonsecin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ff1-1190000000-9f32839fa860a8f53a3b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fonsecin GC-MS (3 TMS) - 70eV, Positive	splash10-007o-3003900000-a0481e8670fc5a42371c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fonsecin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fonsecin LC-ESI-qTof , Positive-QTOF	splash10-0159-0890000000-1870c63ea48978d82743	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fonsecin , positive-QTOF	splash10-0159-0890000000-1870c63ea48978d82743	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fonsecin , positive-QTOF	splash10-001i-0390000000-864a85c4e93db9f756f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fonsecin , positive-QTOF	splash10-0a4i-0190000000-f52e6d79565141004769	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 10V, Positive-QTOF	splash10-0006-0090000000-8698fa82be4165228c8f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 20V, Positive-QTOF	splash10-006x-1090000000-dec5fb573943e34a6899	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 40V, Positive-QTOF	splash10-0ue9-0190000000-c8fcaf793d80a22f301c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 10V, Negative-QTOF	splash10-000i-0090000000-1d309636cbe4d6d7b478	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 20V, Negative-QTOF	splash10-052r-0090000000-bd992c02ee453436b569	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 40V, Negative-QTOF	splash10-0a59-4390000000-621bb98153ac85cae2d7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 10V, Negative-QTOF	splash10-000i-0090000000-4a89100bf019d25eb21a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 20V, Negative-QTOF	splash10-0a5i-0090000000-6fd94ee6fc378b952726	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 40V, Negative-QTOF	splash10-000x-2090000000-4f9de4f27c3a166ba507	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 10V, Positive-QTOF	splash10-0006-0090000000-9a08772e651d55df45c3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 20V, Positive-QTOF	splash10-000x-0090000000-2d9c01b86f47e30e9a7f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin 40V, Positive-QTOF	splash10-0012-0590000000-34ac37097cfe3a189565	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

FDB012396

KNApSAcK ID

C00000559

Chemspider ID

187517

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

216328

PDB ID

Not Available

ChEBI ID

64543

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 Fonsecin (HMDB0034124)

MOL for HMDB0034124 (Fonsecin)

3D MOL for HMDB0034124 (Fonsecin)

3D SDF for HMDB0034124 (Fonsecin)

3D-SDF for HMDB0034124 (Fonsecin)

PDB for HMDB0034124 (Fonsecin)

3D PDB for HMDB0034124 (Fonsecin)

SMILES for HMDB0034124 (Fonsecin)

INCHI for HMDB0034124 (Fonsecin)

Structure for HMDB0034124 (Fonsecin)

3D Structure for HMDB0034124 (Fonsecin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra