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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:38:23 UTC

Update Date

2022-03-07 02:53:53 UTC

HMDB ID

HMDB0033866

Secondary Accession Numbers

HMDB33866

Metabolite Identification

Common Name

Fonsecin B

Description

Fonsecin B, also known as TMC 256 B2, 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 B 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 Fonsecin B.

Structure

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

HMDB0033866
     RDKit          3D
Fonsecin B
 38 40  0  0  0  0  0  0  0  0999 V2000
   -5.3257    1.9440   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229    2.4326   -0.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655    1.5313   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    0.1897   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590   -0.6933   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -2.0575   -0.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5988   -2.6459   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -0.2035    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -1.1205    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -2.4559   -0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737   -0.6833    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    0.6876    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    1.5722    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    1.1375    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    2.0372    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186    1.0440    0.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0700    0.3971   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    0.7414    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0181    0.8783   -1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -1.1034   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6275   -1.5776    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -2.7210    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3719    1.3085   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6427    1.3103    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    2.8223   -0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2160   -0.1782   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900   -3.6482   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333   -2.0241   -1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -2.7110    0.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633   -3.1680   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    2.6288    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    3.0943    0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059    0.5960   -0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795    1.7798    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    0.0846    1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786    1.8188   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -1.4408   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005   -1.6039    0.5303 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
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 15  3  1  0
 14  8  1  0
 21 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061307242D          

 22 24  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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    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
    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
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 12  5  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16  7  1  0  0  0  0
 17 10  2  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20  2  1  0  0  0  0
 20  9  1  0  0  0  0
 21  3  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033866

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-16(19)7-10(17)14-12(22-16)5-8-4-9(20-2)6-11(21-3)13(8)15(14)18/h4-6,18-19H,7H2,1-3H3

> <INCHI_KEY>
ZYTKFYQKQVYVMW-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.2946

> <EXACT_MASS>
304.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.656956692359646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
2.215971515666666

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.877839388664032

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.288644137762716

> <JCHEM_PKA_STRONGEST_BASIC>
-4.158630216762281

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
78.47350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033866
     RDKit          3D
Fonsecin B
 38 40  0  0  0  0  0  0  0  0999 V2000
   -5.3257    1.9440   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229    2.4326   -0.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655    1.5313   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    0.1897   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590   -0.6933   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -2.0575   -0.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5988   -2.6459   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -0.2035    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -1.1205    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -2.4559   -0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737   -0.6833    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    0.6876    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    1.5722    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    1.1375    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    2.0372    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186    1.0440    0.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0700    0.3971   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    0.7414    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0181    0.8783   -1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -1.1034   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6275   -1.5776    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -2.7210    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3719    1.3085   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6427    1.3103    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    2.8223   -0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2160   -0.1782   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900   -3.6482   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333   -2.0241   -1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -2.7110    0.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633   -3.1680   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    2.6288    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    3.0943    0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059    0.5960   -0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795    1.7798    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    0.0846    1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786    1.8188   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -1.4408   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005   -1.6039    0.5303 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
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 15  3  1  0
 14  8  1  0
 21 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+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       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    8    9                                                       
CONECT    5    8   12                                                       
CONECT    6    9   11                                                       
CONECT    7   10   16                                                       
CONECT    8    4    5   13                                                  
CONECT    9    4    6   20                                                  
CONECT   10    7   14   17                                                  
CONECT   11    6   13   21                                                  
CONECT   12    5   14   22                                                  
CONECT   13    8   11   15                                                  
CONECT   14   10   12   15                                                  
CONECT   15   13   14   18                                                  
CONECT   16    1    7   19   22                                             
CONECT   17   10                                                            
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20    2    9                                                       
CONECT   21    3   11                                                       
CONECT   22   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0033866
HETATM    1  C1  UNL     1      -5.326   1.944  -0.279  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.023   2.433  -0.076  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.965   1.531  -0.041  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.216   0.190  -0.205  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.159  -0.693  -0.168  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.340  -2.058  -0.326  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.599  -2.646  -0.534  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.866  -0.204   0.034  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.200  -1.121   0.069  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.087  -2.456  -0.100  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.474  -0.683   0.264  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.693   0.688   0.427  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.649   1.572   0.391  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.645   1.138   0.195  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.700   2.037   0.160  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.019   1.044   0.619  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.070   0.397  -0.083  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.401   0.741   0.510  1.00  0.00           C  
HETATM   19  O5  UNL     1       4.018   0.878  -1.390  1.00  0.00           O  
HETATM   20  C15 UNL     1       3.936  -1.103  -0.116  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.628  -1.578   0.328  1.00  0.00           C  
HETATM   22  O6  UNL     1       2.471  -2.721   0.758  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.372   1.309  -1.183  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.643   1.310   0.588  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.003   2.822  -0.343  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.216  -0.178  -0.360  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.490  -3.648  -1.036  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.233  -2.024  -1.226  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.127  -2.711   0.429  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.563  -3.168  -0.112  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.810   2.629   0.516  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.496   3.094   0.290  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.206   0.596  -0.263  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.480   1.780   0.869  1.00  0.00           H  
HETATM   35  H13 UNL     1       5.657   0.085   1.371  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.379   1.819  -1.351  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.152  -1.441  -1.148  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.700  -1.604   0.530  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   15
CONECT    4    5   26
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   27   28   29
CONECT    8    9   14
CONECT    9   10   11   11
CONECT   10   30
CONECT   11   12   21
CONECT   12   13   13   16
CONECT   13   14   31
CONECT   14   15   15
CONECT   15   32
CONECT   16   17
CONECT   17   18   19   20
CONECT   18   33   34   35
CONECT   19   36
CONECT   20   21   37   38
CONECT   21   22   22
END

HMDB0033866
     RDKit          3D
Fonsecin B
 38 40  0  0  0  0  0  0  0  0999 V2000
   -5.3257    1.9440   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0229    2.4326   -0.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655    1.5313   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158    0.1897   -0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1590   -0.6933   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3396   -2.0575   -0.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5988   -2.6459   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8659   -0.2035    0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002   -1.1205    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -2.4559   -0.1002 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4737   -0.6833    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    0.6876    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486    1.5722    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    1.1375    0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    2.0372    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0186    1.0440    0.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0700    0.3971   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4012    0.7414    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0181    0.8783   -1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -1.1034   -0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6275   -1.5776    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -2.7210    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3719    1.3085   -1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6427    1.3103    0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0028    2.8223   -0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2160   -0.1782   -0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900   -3.6482   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2333   -2.0241   -1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1265   -2.7110    0.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633   -3.1680   -0.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103    2.6288    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4956    3.0943    0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2059    0.5960   -0.2628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4795    1.7798    0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    0.0846    1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3786    1.8188   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -1.4408   -1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7005   -1.6039    0.5303 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
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 15  3  1  0
 14  8  1  0
 21 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 10 30  1  0
 13 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5-Dihydroxy-6,8-dimethoxy-2-methyl-2,3-dihydro-4H-naphtho[2,3-b]pyran-4-one	ChEBI
2,5-Dihydroxy-6,8-dimethoxy-2-methyl-2.3-dihydrobenzo[g]chromen-4-one	ChEBI
Fonsecin monomethyl ether	ChEBI
TMC 256 b2	ChEBI
TMC-256b2	ChEBI
TMC256b2	ChEBI
Antibiotic TMC 256b2	HMDB
TMC 256b2	HMDB

Chemical Formula

C₁₆H₁₆O₆

Average Molecular Weight

304.2946

Monoisotopic Molecular Weight

304.094688244

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1856-95-7

SMILES

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

InChI Identifier

InChI=1S/C16H16O6/c1-16(19)7-10(17)14-12(22-16)5-8-4-9(20-2)6-11(21-3)13(8)15(14)18/h4-6,18-19H,7H2,1-3H3

InChI Key

ZYTKFYQKQVYVMW-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
1-naphthol
Chromane
Benzopyran
Naphthalene
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Pyran
Benzenoid
Vinylogous acid
Ketone
Hemiacetal
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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: HMDB0033866)
Cytoplasm (HMDB: HMDB0033866)

Source

Exogenous

Food

Food (HMDB: HMDB0033866)

Not Available

Nutrient (HMDB: HMDB0033866)

Environmental role

Environmental contaminant (HMDB: HMDB0033866)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	176 °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	0.29 g/L	ALOGPS
logP	1.47	ALOGPS
logP	2.22	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.47 m³·mol⁻¹	ChemAxon
Polarizability	30.66 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.456	31661259
DarkChem	[M-H]-	172.935	31661259
DeepCCS	[M+H]+	175.491	30932474
DeepCCS	[M-H]-	173.133	30932474
DeepCCS	[M-2H]-	207.093	30932474
DeepCCS	[M+Na]+	182.32	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.2	32859911
AllCCS	[M+HCOO]-	173.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fonsecin B	COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=C1	3946.8	Standard polar	33892256
Fonsecin B	COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=C1	2709.6	Standard non polar	33892256
Fonsecin B	COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O)OC3=CC2=C1	2713.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fonsecin B,1TMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C)=C3C(=O)CC(C)(O)OC3=CC2=C1	2674.0	Semi standard non polar	33892256
Fonsecin B,1TMS,isomer #2	COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O[Si](C)(C)C)OC3=CC2=C1	2608.5	Semi standard non polar	33892256
Fonsecin B,2TMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C)=C3C(=O)CC(C)(O[Si](C)(C)C)OC3=CC2=C1	2658.5	Semi standard non polar	33892256
Fonsecin B,1TBDMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)CC(C)(O)OC3=CC2=C1	2882.2	Semi standard non polar	33892256
Fonsecin B,1TBDMS,isomer #2	COC1=CC(OC)=C2C(O)=C3C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)OC3=CC2=C1	2842.8	Semi standard non polar	33892256
Fonsecin B,2TBDMS,isomer #1	COC1=CC(OC)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)CC(C)(O[Si](C)(C)C(C)(C)C)OC3=CC2=C1	3093.4	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 B GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pa-1090000000-caf70b76d1736aca171b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fonsecin B GC-MS (2 TMS) - 70eV, Positive	splash10-003r-4009800000-3a30b25e7fdd1fc35e2d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fonsecin B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fonsecin B 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 - Fonsecin B 10V, Positive-QTOF	splash10-0a4i-0079000000-bf437d6e9b14ac7fcebb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 20V, Positive-QTOF	splash10-0a4r-1094000000-91e1c9a018e78d4add49	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 40V, Positive-QTOF	splash10-00kb-1290000000-0ce998f5b0b466a8d448	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 10V, Negative-QTOF	splash10-0udi-0069000000-066645bde46f7ee064f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 20V, Negative-QTOF	splash10-0udi-1094000000-8a4888711d69d6b7cc1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 40V, Negative-QTOF	splash10-0udi-1390000000-ccb1eb485faeba81cc52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 10V, Negative-QTOF	splash10-0udi-0009000000-aad98767acd0285db910	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 20V, Negative-QTOF	splash10-014j-0091000000-51789fb628e383733296	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 40V, Negative-QTOF	splash10-0a4l-7090000000-cbc4700ed7afbb28b9b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 10V, Positive-QTOF	splash10-0a4i-0039000000-34cd6f4a45fe5457c8ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 20V, Positive-QTOF	splash10-0a4j-0096000000-46024f8a4eefd44cfe61	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fonsecin B 40V, Positive-QTOF	splash10-0h01-0490000000-fb7e38ebbe11e4cd1448	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012050

KNApSAcK ID

C00034518

Chemspider ID

141119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160596

PDB ID

Not Available

ChEBI ID

133825

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 B (HMDB0033866)

MOL for HMDB0033866 (Fonsecin B)

3D MOL for HMDB0033866 (Fonsecin B)

3D SDF for HMDB0033866 (Fonsecin B)

3D-SDF for HMDB0033866 (Fonsecin B)

PDB for HMDB0033866 (Fonsecin B)

3D PDB for HMDB0033866 (Fonsecin B)

SMILES for HMDB0033866 (Fonsecin B)

INCHI for HMDB0033866 (Fonsecin B)

Structure for HMDB0033866 (Fonsecin B)

3D Structure for HMDB0033866 (Fonsecin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra