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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:52:25 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038549

Secondary Accession Numbers

HMDB38549

Metabolite Identification

Common Name

Toralactone

Description

Toralactone 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. Toralactone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make toralactone a potential biomarker for the consumption of these foods. Toralactone 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 Toralactone.

Structure

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

HMDB0038549
     RDKit          3D
Toralactone
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.7116    1.8387   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5446    0.4313    0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411   -0.0631    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0816   -1.4162    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877   -1.9495    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6468   -3.3301    0.3350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652   -1.1591    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033   -1.7033    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -3.0227    0.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831   -0.8010    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -1.2896    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -2.5220    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9673   -0.4453    0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    0.8351    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0441    1.7112   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    1.3990   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843    0.5449    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175    1.0737   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675    0.2125    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.7588    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    2.2061   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638    2.1372   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    2.2834    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132   -2.1193    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -3.9681    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981   -3.8344    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7761    2.7712   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7245    1.5232    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5903    1.4825   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201    2.4477   -0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973    2.1424   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    1.8249   -0.0620 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 20 32  1  0
M  END

  Mrv0541 05061310312D          

 20 22  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 19  2  1  0  0  0  0
 19 10  1  0  0  0  0
 20  7  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038549

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3

> <INCHI_KEY>
WEHXAEGTVPWKDY-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.479918076704386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10-dihydroxy-7-methoxy-3-methyl-1H-benzo[g]isochromen-1-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.1301378890000002

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.656418012712935

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.448629138871892

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4827965879874165

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
74.1803

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,10-dihydroxy-7-methoxy-3-methylbenzo[g]isochromen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038549
     RDKit          3D
Toralactone
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.7116    1.8387   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5446    0.4313    0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411   -0.0631    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0816   -1.4162    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877   -1.9495    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6468   -3.3301    0.3350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652   -1.1591    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033   -1.7033    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -3.0227    0.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831   -0.8010    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -1.2896    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -2.5220    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9673   -0.4453    0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    0.8351    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0441    1.7112   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    1.3990   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843    0.5449    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175    1.0737   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675    0.2125    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.7588    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    2.2061   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638    2.1372   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    2.2834    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132   -2.1193    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -3.9681    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981   -3.8344    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7761    2.7712   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7245    1.5232    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5903    1.4825   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201    2.4477   -0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973    2.1424   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    1.8249   -0.0620 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 20 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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -0.770   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   19                                                            
CONECT    3    7    8                                                       
CONECT    4    8    9                                                       
CONECT    5    9   10                                                       
CONECT    6   10   11                                                       
CONECT    7    1    3   20                                                  
CONECT    8    3    4   13                                                  
CONECT    9    4    5   12                                                  
CONECT   10    5    6   19                                                  
CONECT   11    6   12   16                                                  
CONECT   12    9   11   14                                                  
CONECT   13    8   14   15                                                  
CONECT   14   12   13   17                                                  
CONECT   15   13   18   20                                                  
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19    2   10                                                       
CONECT   20    7   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0038549
HETATM    1  C1  UNL     1       4.712   1.839  -0.063  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.545   0.431   0.045  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.241  -0.063   0.083  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.082  -1.416   0.188  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.788  -1.950   0.229  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.647  -3.330   0.335  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.665  -1.159   0.168  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.603  -1.703   0.210  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.903  -3.023   0.312  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.683  -0.801   0.141  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.968  -1.290   0.178  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.145  -2.522   0.273  1.00  0.00           O  
HETATM   13  O5  UNL     1      -3.967  -0.445   0.113  1.00  0.00           O  
HETATM   14  C9  UNL     1      -3.841   0.835   0.015  1.00  0.00           C  
HETATM   15  C10 UNL     1      -5.044   1.711  -0.053  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.592   1.399  -0.029  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.484   0.545   0.037  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.218   1.074  -0.004  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.868   0.213   0.062  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.146   0.759   0.020  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.183   2.206  -0.966  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.764   2.137  -0.069  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.231   2.283   0.839  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.913  -2.119   0.242  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.407  -3.968   0.384  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.398  -3.834   0.374  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.776   2.771  -0.063  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.724   1.523   0.821  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.590   1.483  -0.996  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.420   2.448  -0.110  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.097   2.142  -0.086  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.264   1.825  -0.062  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   19
CONECT    8    9   10   10
CONECT    9   26
CONECT   10   11   17
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   16   16
CONECT   15   27   28   29
CONECT   16   17   30
CONECT   17   18   18
CONECT   18   19   31
CONECT   19   20   20
CONECT   20   32
END

HMDB0038549
     RDKit          3D
Toralactone
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.7116    1.8387   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5446    0.4313    0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2411   -0.0631    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0816   -1.4162    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877   -1.9495    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6468   -3.3301    0.3350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652   -1.1591    0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033   -1.7033    0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030   -3.0227    0.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831   -0.8010    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -1.2896    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450   -2.5220    0.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9673   -0.4453    0.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    0.8351    0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0441    1.7112   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    1.3990   -0.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843    0.5449    0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175    1.0737   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8675    0.2125    0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1461    0.7588    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    2.2061   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638    2.1372   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    2.2834    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9132   -2.1193    0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075   -3.9681    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981   -3.8344    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7761    2.7712   -0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7245    1.5232    0.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5903    1.4825   -0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4201    2.4477   -0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0973    2.1424   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    1.8249   -0.0620 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  3  1  0
 19  7  1  0
 17 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  9 26  1  0
 15 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho(2,3-c)pyran-1-one	ChEBI
9,10-Dihydroxy-7-methoxy-3-methyl-1H-naphtho[2,3-c]pyran-1-one, 9ci	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

9,10-dihydroxy-7-methoxy-3-methyl-1H-benzo[g]isochromen-1-one

Traditional Name

9,10-dihydroxy-7-methoxy-3-methylbenzo[g]isochromen-1-one

CAS Registry Number

41743-74-2

SMILES

COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1

InChI Identifier

InChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3

InChI Key

WEHXAEGTVPWKDY-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
Isocoumarin
1-naphthol
Benzopyran
Naphthalene
2-benzopyran
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:78029 )
organic heterotricyclic compound (CHEBI:78029 )
phenols (CHEBI:78029 )
polyketide (CHEBI:78029 )
lactone (CHEBI:78029 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038549)
Cell membrane (HMDB: HMDB0038549)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038549)

Source

Exogenous

Exogenous (HMDB: HMDB0038549)

Food

Food (HMDB: HMDB0038549)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Not Available

Nutrient (HMDB: HMDB0038549)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	252 - 254 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	34.72 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.18 m³·mol⁻¹	ChemAxon
Polarizability	27.48 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]+	164.235	31661259
DarkChem	[M-H]-	165.486	31661259
DeepCCS	[M+H]+	163.683	30932474
DeepCCS	[M-H]-	161.325	30932474
DeepCCS	[M-2H]-	194.313	30932474
DeepCCS	[M+Na]+	169.776	30932474
AllCCS	[M+H]+	160.3	32859911
AllCCS	[M+H-H2O]+	156.4	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Toralactone	COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1	3981.5	Standard polar	33892256
Toralactone	COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1	2551.1	Standard non polar	33892256
Toralactone	COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1	2676.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Toralactone,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1	2850.2	Semi standard non polar	33892256
Toralactone,1TMS,isomer #2	COC1=CC(O)=C2C(O[Si](C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1	2843.8	Semi standard non polar	33892256
Toralactone,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1	2925.0	Semi standard non polar	33892256
Toralactone,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1	3059.4	Semi standard non polar	33892256
Toralactone,1TBDMS,isomer #2	COC1=CC(O)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1	3053.4	Semi standard non polar	33892256
Toralactone,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)OC(C)=CC3=CC2=C1	3324.4	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 - Toralactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abc-0190000000-0b6644937e0069cfba34	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Toralactone GC-MS (2 TMS) - 70eV, Positive	splash10-0uk9-2009400000-28388824cb8fdaf3e748	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Toralactone 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 - Toralactone 10V, Positive-QTOF	splash10-00di-0090000000-af0e4aa15b772877e705	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 20V, Positive-QTOF	splash10-00di-0090000000-67a31feccf2de0c2d09c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 40V, Positive-QTOF	splash10-002b-0890000000-b766d9ba09c1aa5c07ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 10V, Negative-QTOF	splash10-00di-0090000000-a304bd0b8e4313937885	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 20V, Negative-QTOF	splash10-00di-0090000000-b199e2cdf9b618446ccb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 40V, Negative-QTOF	splash10-004j-1980000000-284d4a71b00b8c9cc8c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 10V, Positive-QTOF	splash10-00di-0090000000-031a5312b116bdf1aa4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 20V, Positive-QTOF	splash10-00di-0090000000-e8cad39c3f9c861b9b61	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 40V, Positive-QTOF	splash10-0fi9-0490000000-d32339d75f0f0ea86780	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 10V, Negative-QTOF	splash10-00di-0090000000-d6b6f6391b4e9f4522f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 20V, Negative-QTOF	splash10-00di-0090000000-d6b6f6391b4e9f4522f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toralactone 40V, Negative-QTOF	splash10-00dj-3970000000-0694d792101fade0dd10	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321980

PDB ID

Not Available

ChEBI ID

78029

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1351071

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 Toralactone (HMDB0038549)

MOL for HMDB0038549 (Toralactone)

3D MOL for HMDB0038549 (Toralactone)

3D SDF for HMDB0038549 (Toralactone)

3D-SDF for HMDB0038549 (Toralactone)

PDB for HMDB0038549 (Toralactone)

3D PDB for HMDB0038549 (Toralactone)

SMILES for HMDB0038549 (Toralactone)

INCHI for HMDB0038549 (Toralactone)

Structure for HMDB0038549 (Toralactone)

3D Structure for HMDB0038549 (Toralactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra