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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:47:36 UTC

Update Date

2022-03-07 02:55:47 UTC

HMDB ID

HMDB0038473

Secondary Accession Numbers

HMDB38473

Metabolite Identification

Common Name

Torachrysone

Description

Torachrysone belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Torachrysone 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 torachrysone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Torachrysone.

Structure

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

HMDB0038473
     RDKit          3D
Torachrysone
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.1087   -0.3365    0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.0516   -0.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501    0.0220   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    0.3166   -1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    0.4081   -1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.7057   -3.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035    0.2091   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    0.2970   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163    0.5826   -2.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    0.0912   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3977    0.1973   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5473    0.0458    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    0.4777   -1.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -0.1980    1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -0.4356    2.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.2893    1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876   -0.0868    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1576   -0.1764    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5469   -0.0518    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3507   -1.4377    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0939    0.1754    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336    0.4811   -2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    0.8574   -4.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3652    0.7728   -3.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897   -1.0339    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    0.5154    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5050    0.4223   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758   -0.8827    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -1.1914    2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345    0.5278    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084   -0.5239    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.4096    1.4997 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  1  0
 11 13  2  0
 10 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  9 24  1  0
 12 25  1  0
 12 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
M  END

  Mrv0541 05061310292D          

 18 19  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    1.4289    0.0000    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
    3.5724   -1.2375    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
    0.0000   -1.6500    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
    3.5724   -0.4125    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
    0.7145   -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
    1.4289   -1.6500    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
    2.8579   -2.4750    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
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  4  2  0  0  0  0
  8  2  1  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  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  8  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18  3  1  0  0  0  0
 18 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038473

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-7-4-9-5-10(18-3)6-11(16)13(9)14(17)12(7)8(2)15/h4-6,16-17H,1-3H3

> <INCHI_KEY>
BIJOPUWEMBBDEG-UHFFFAOYSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.2586

> <EXACT_MASS>
246.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.80368410838894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(1,8-dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethan-1-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.9189895716666663

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.208568995564919

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.303635089236668

> <JCHEM_PKA_STRONGEST_BASIC>
-4.369000026183454

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
68.37720000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(1,8-dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038473
     RDKit          3D
Torachrysone
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.1087   -0.3365    0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.0516   -0.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501    0.0220   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    0.3166   -1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    0.4081   -1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.7057   -3.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035    0.2091   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    0.2970   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163    0.5826   -2.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    0.0912   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3977    0.1973   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5473    0.0458    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    0.4777   -1.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -0.1980    1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -0.4356    2.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.2893    1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876   -0.0868    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1576   -0.1764    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5469   -0.0518    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3507   -1.4377    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0939    0.1754    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336    0.4811   -2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    0.8574   -4.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3652    0.7728   -3.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897   -1.0339    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    0.5154    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5050    0.4223   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758   -0.8827    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -1.1914    2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345    0.5278    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084   -0.5239    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.4096    1.4997 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  1  0
 11 13  2  0
 10 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  9 24  1  0
 12 25  1  0
 12 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   18                                                            
CONECT    4    7    9                                                       
CONECT    5    9   10                                                       
CONECT    6   10   11                                                       
CONECT    7    1    4   12                                                  
CONECT    8    2   12   15                                                  
CONECT    9    4    5   13                                                  
CONECT   10    5    6   18                                                  
CONECT   11    6   13   16                                                  
CONECT   12    7    8   14                                                  
CONECT   13    9   11   14                                                  
CONECT   14   12   13   17                                                  
CONECT   15    8                                                            
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    3   10                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0038473
HETATM    1  C1  UNL     1       5.109  -0.337   0.802  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.428  -0.052  -0.380  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.050   0.022  -0.512  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.550   0.317  -1.763  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.185   0.408  -1.978  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.756   0.706  -3.253  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.303   0.209  -0.956  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.060   0.297  -1.153  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.616   0.583  -2.355  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.990   0.091  -0.093  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.398   0.197  -0.358  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.547   0.046   0.514  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.706   0.478  -1.590  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.470  -0.198   1.130  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.333  -0.436   2.300  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.081  -0.289   1.338  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.788  -0.087   0.304  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.158  -0.176   0.508  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.547  -0.052   1.697  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.351  -1.438   0.862  1.00  0.00           H  
HETATM   21  H3  UNL     1       6.094   0.175   0.756  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.234   0.481  -2.602  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.388   0.857  -4.026  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.365   0.773  -3.246  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.790  -1.034   0.646  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.520   0.515   1.494  1.00  0.00           H  
HETATM   27  H9  UNL     1      -5.505   0.422  -0.010  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.676  -0.883   3.136  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.104  -1.191   2.186  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.635   0.528   2.764  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.308  -0.524   2.339  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.548  -0.410   1.500  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   22
CONECT    5    6    7    7
CONECT    6   23
CONECT    7    8   17
CONECT    8    9   10   10
CONECT    9   24
CONECT   10   11   14
CONECT   11   12   13   13
CONECT   12   25   26   27
CONECT   14   15   16   16
CONECT   15   28   29   30
CONECT   16   17   31
CONECT   17   18   18
CONECT   18   32
END

HMDB0038473
     RDKit          3D
Torachrysone
 32 33  0  0  0  0  0  0  0  0999 V2000
    5.1087   -0.3365    0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4279   -0.0516   -0.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0501    0.0220   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497    0.3166   -1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854    0.4081   -1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.7057   -3.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035    0.2091   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601    0.2970   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163    0.5826   -2.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    0.0912   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3977    0.1973   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5473    0.0458    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062    0.4777   -1.5897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -0.1980    1.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -0.4356    2.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806   -0.2893    1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876   -0.0868    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1576   -0.1764    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5469   -0.0518    1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3507   -1.4377    0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0939    0.1754    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336    0.4811   -2.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3881    0.8574   -4.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3652    0.7728   -3.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7897   -1.0339    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5199    0.5154    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5050    0.4223   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758   -0.8827    3.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -1.1914    2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345    0.5278    2.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3084   -0.5239    2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5478   -0.4096    1.4997 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  1  0
 11 13  2  0
 10 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
 17  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  9 24  1  0
 12 25  1  0
 12 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-nitroso-1-Phenyl-urea	HMDB
2-Acetyl-1,8-dihydroxy-6-methoxy-3-methylnaphthalene	HMDB
N-nitroso-N-Phenyl-urea	HMDB
N-Phenyl-N-nitrosourea	HMDB
Nakahalene	HMDB
Nitrosophenylurea	HMDB
Phenyl-nitroso-harnstoff	HMDB
Urea, 1-nitroso-1-phenyl- (8ci)	HMDB

Chemical Formula

C₁₄H₁₄O₄

Average Molecular Weight

246.2586

Monoisotopic Molecular Weight

246.089208936

IUPAC Name

1-(1,8-dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethan-1-one

Traditional Name

1-(1,8-dihydroxy-6-methoxy-3-methylnaphthalen-2-yl)ethanone

CAS Registry Number

22649-04-3

SMILES

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

InChI Identifier

InChI=1S/C14H14O4/c1-7-4-9-5-10(18-3)6-11(16)13(9)14(17)12(7)8(2)15/h4-6,16-17H,1-3H3

InChI Key

BIJOPUWEMBBDEG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
Acetophenone
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthols (CHEBI:81265 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038473)
Cell membrane (HMDB: HMDB0038473)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038473)

Source

Exogenous

Exogenous (HMDB: HMDB0038473)

Food

Food (HMDB: HMDB0038473)

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: HMDB0038473)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	214 - 215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	144.9 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	0.14 g/L	ALOGPS
logP	2.71	ALOGPS
logP	2.92	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.38 m³·mol⁻¹	ChemAxon
Polarizability	25.8 Å³	ChemAxon
Number of Rings	2	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]+	158.412	31661259
DarkChem	[M-H]-	160.601	31661259
DeepCCS	[M+H]+	159.134	30932474
DeepCCS	[M-H]-	156.776	30932474
DeepCCS	[M-2H]-	189.662	30932474
DeepCCS	[M+Na]+	165.227	30932474
AllCCS	[M+H]+	154.9	32859911
AllCCS	[M+H-H2O]+	151.0	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.6	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Torachrysone	COC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C1	3514.4	Standard polar	33892256
Torachrysone	COC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C1	2210.1	Standard non polar	33892256
Torachrysone	COC1=CC(O)=C2C(O)=C(C(C)=O)C(C)=CC2=C1	2352.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Torachrysone,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(O)=C(C(C)=O)C(C)=CC2=C1	2292.6	Semi standard non polar	33892256
Torachrysone,1TMS,isomer #2	COC1=CC(O)=C2C(O[Si](C)(C)C)=C(C(C)=O)C(C)=CC2=C1	2245.2	Semi standard non polar	33892256
Torachrysone,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=C(C(C)=O)C(C)=CC2=C1	2294.3	Semi standard non polar	33892256
Torachrysone,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O)=C(C(C)=O)C(C)=CC2=C1	2521.2	Semi standard non polar	33892256
Torachrysone,1TBDMS,isomer #2	COC1=CC(O)=C2C(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(C)=CC2=C1	2486.7	Semi standard non polar	33892256
Torachrysone,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(O[Si](C)(C)C(C)(C)C)=C(C(C)=O)C(C)=CC2=C1	2740.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Torachrysone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1290000000-cc6d5507e5ef3cc44ebe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Torachrysone GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-3019000000-f6b04c5681ef95652745	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Torachrysone 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 - Torachrysone 10V, Positive-QTOF	splash10-0002-0090000000-38e6500d2b0161c2695d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 20V, Positive-QTOF	splash10-0002-0090000000-b69e0a7f88e6278aeff6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 40V, Positive-QTOF	splash10-0002-2950000000-8f1383df87601c2a2b83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 10V, Negative-QTOF	splash10-0002-0090000000-83a949d132fc002a3d9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 20V, Negative-QTOF	splash10-0002-0090000000-0d630fd9238182ff4ed1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 40V, Negative-QTOF	splash10-0fka-2950000000-afc055777a0868e84679	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 10V, Negative-QTOF	splash10-0002-0090000000-f3df51ecec20c65b25b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 20V, Negative-QTOF	splash10-0f6t-0090000000-998da1a0209fcb197258	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 40V, Negative-QTOF	splash10-03dj-1910000000-ecc17d89c6faf2444a0d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 10V, Positive-QTOF	splash10-0002-0090000000-30fbf0a5a6d5a52e1a95	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 20V, Positive-QTOF	splash10-004j-0090000000-d3441a5332d9bec8bd7c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torachrysone 40V, Positive-QTOF	splash10-08i9-4920000000-a1bb758ff61860b6779b	2021-09-25	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

5321977

PDB ID

Not Available

ChEBI ID

81265

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1868611

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 Torachrysone (HMDB0038473)

MOL for HMDB0038473 (Torachrysone)

3D MOL for HMDB0038473 (Torachrysone)

3D SDF for HMDB0038473 (Torachrysone)

3D-SDF for HMDB0038473 (Torachrysone)

PDB for HMDB0038473 (Torachrysone)

3D PDB for HMDB0038473 (Torachrysone)

SMILES for HMDB0038473 (Torachrysone)

INCHI for HMDB0038473 (Torachrysone)

Structure for HMDB0038473 (Torachrysone)

3D Structure for HMDB0038473 (Torachrysone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra