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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:41:10 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033911

Secondary Accession Numbers

HMDB33911

Metabolite Identification

Common Name

5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one

Description

5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one, also known as 5,6,8-trihydroxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one or nor-rubrofusarin, 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. 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 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 5,6,8-trihydroxy-2-methylbenzo[g]chromen-4-one a potential biomarker for the consumption of these foods. 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 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 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one.

Structure

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

HMDB0033911
     RDKit          3D
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6909    1.2887   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568    0.6028   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.7042    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -1.3794    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -2.5624    0.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -0.6685    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -1.2565    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387   -2.5459    0.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626   -0.4948    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117   -1.0906    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -2.3635    0.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8514   -0.3088   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034    0.9839   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567    1.7366   -0.7494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    1.5496   -0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    0.8090   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871    1.3890   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    0.6369   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399    1.2266   -0.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214    0.5305   -0.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545    2.0975   -1.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705    1.6790    0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -1.2389    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925   -3.2896    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590   -3.1558    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -0.7490    0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324    2.2842   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3174    2.5686   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123    2.4246   -0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 18  6  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
M  END


  Mrv0541 05061307262D          

 19 21  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    3.5724    1.2375    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
    2.8579    2.4750    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  2  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  2  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  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033911

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-6-2-9(16)13-11(19-6)4-7-3-8(15)5-10(17)12(7)14(13)18/h2-5,15,17-18H,1H3

> <INCHI_KEY>
RVRLLYKHCMHGKV-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.2262

> <EXACT_MASS>
258.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.41237162722236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,8-trihydroxy-2-methyl-4H-benzo[g]chromen-4-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.600334061

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.81320841253683

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.844878190530161

> <JCHEM_PKA_STRONGEST_BASIC>
-5.339328085445928

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
69.50010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6,8-trihydroxy-2-methylbenzo[g]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033911
     RDKit          3D
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6909    1.2887   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568    0.6028   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.7042    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -1.3794    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -2.5624    0.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -0.6685    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -1.2565    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387   -2.5459    0.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626   -0.4948    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117   -1.0906    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -2.3635    0.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8514   -0.3088   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034    0.9839   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567    1.7366   -0.7494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    1.5496   -0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    0.8090   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871    1.3890   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    0.6369   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399    1.2266   -0.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214    0.5305   -0.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545    2.0975   -1.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705    1.6790    0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -1.2389    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925   -3.2896    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590   -3.1558    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -0.7490    0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324    2.2842   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3174    2.5686   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123    2.4246   -0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 18  6  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  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      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6    9                                                       
CONECT    3    7    8                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    1    2   19                                                  
CONECT    7    3    4   12                                                  
CONECT    8    3    5   15                                                  
CONECT    9    2   13   16                                                  
CONECT   10    5   12   17                                                  
CONECT   11    4   13   19                                                  
CONECT   12    7   10   14                                                  
CONECT   13    9   11   14                                                  
CONECT   14   12   13   18                                                  
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   14                                                            
CONECT   19    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0033911
HETATM    1  C1  UNL     1       4.691   1.289  -0.302  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.357   0.603  -0.129  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.292  -0.704   0.280  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.105  -1.379   0.455  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.058  -2.562   0.826  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.921  -0.669   0.193  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.306  -1.257   0.339  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.439  -2.546   0.741  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.463  -0.495   0.062  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.712  -1.091   0.209  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.919  -2.363   0.604  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.851  -0.309  -0.073  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.703   0.984  -0.475  1.00  0.00           C  
HETATM   14  O4  UNL     1      -4.857   1.737  -0.749  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.463   1.550  -0.614  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.328   0.809  -0.344  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.087   1.389  -0.487  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.054   0.637  -0.214  1.00  0.00           C  
HETATM   19  O5  UNL     1       2.240   1.227  -0.361  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.421   0.530  -0.710  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.554   2.098  -1.041  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.070   1.679   0.647  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.218  -1.239   0.478  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.092  -3.290   0.992  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.459  -3.156   0.868  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.851  -0.749   0.033  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.332   2.284  -0.050  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.317   2.569  -0.930  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.012   2.425  -0.810  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   19
CONECT    3    4   23
CONECT    4    5    5    6
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   24
CONECT    9   10   10   16
CONECT   10   11   12
CONECT   11   25
CONECT   12   13   13   26
CONECT   13   14   15
CONECT   14   27
CONECT   15   16   16   28
CONECT   16   17
CONECT   17   18   18   29
CONECT   18   19
END

HMDB0033911
     RDKit          3D
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one
 29 31  0  0  0  0  0  0  0  0999 V2000
    4.6909    1.2887   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3568    0.6028   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.7042    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046   -1.3794    0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -2.5624    0.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -0.6685    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -1.2565    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387   -2.5459    0.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626   -0.4948    0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7117   -1.0906    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -2.3635    0.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8514   -0.3088   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034    0.9839   -0.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8567    1.7366   -0.7494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    1.5496   -0.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    0.8090   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0871    1.3890   -0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    0.6369   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2399    1.2266   -0.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4214    0.5305   -0.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545    2.0975   -1.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705    1.6790    0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176   -1.2389    0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925   -3.2896    0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590   -3.1558    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512   -0.7490    0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3324    2.2842   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3174    2.5686   -0.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123    2.4246   -0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  2  1  0
 18  6  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6,8-Trihydroxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one	ChEBI
Nor-rubrofusarin	ChEBI
Norrubrofusarin	HMDB

Chemical Formula

C₁₄H₁₀O₅

Average Molecular Weight

258.2262

Monoisotopic Molecular Weight

258.05282343

IUPAC Name

5,6,8-trihydroxy-2-methyl-4H-benzo[g]chromen-4-one

Traditional Name

5,6,8-trihydroxy-2-methylbenzo[g]chromen-4-one

CAS Registry Number

3566-98-1

SMILES

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

InChI Identifier

InChI=1S/C14H10O5/c1-6-2-9(16)13-11(19-6)4-7-3-8(15)5-10(17)12(7)14(13)18/h2-5,15,17-18H,1H3

InChI Key

RVRLLYKHCMHGKV-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
Chromone
2-naphthol
1-naphthol
Benzopyran
Naphthalene
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Polyol
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:81264 )
organooxygen compound (CHEBI:81264 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033911)

Cellular substructure

Membrane (HMDB: HMDB0033911)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033911)

Source

Exogenous

Food

Food (HMDB: HMDB0033911)

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: HMDB0033911)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	298 - 299 °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	0.27 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.6	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.5 m³·mol⁻¹	ChemAxon
Polarizability	25.41 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
DeepCCS	[M+H]+	160.448	30932474
DeepCCS	[M-H]-	158.06	30932474
DeepCCS	[M-2H]-	190.946	30932474
DeepCCS	[M+Na]+	166.511	30932474
AllCCS	[M+H]+	156.3	32859911
AllCCS	[M+H-H2O]+	152.3	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.1	32859911
AllCCS	[M-H]-	157.5	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	156.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one	CC1=CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1	4072.9	Standard polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one	CC1=CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1	2522.2	Standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one	CC1=CC(=O)C2=C(O)C3=C(O)C=C(O)C=C3C=C2O1	2700.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,1TMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C)C3=C(O)C=C(O)C=C3C=C2O1	2797.6	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,1TMS,isomer #2	CC1=CC(=O)C2=C(O)C3=C(O[Si](C)(C)C)C=C(O)C=C3C=C2O1	2832.3	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,1TMS,isomer #3	CC1=CC(=O)C2=C(O)C3=C(O)C=C(O[Si](C)(C)C)C=C3C=C2O1	2863.4	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,2TMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C)C3=C(O[Si](C)(C)C)C=C(O)C=C3C=C2O1	2791.8	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,2TMS,isomer #2	CC1=CC(=O)C2=C(O[Si](C)(C)C)C3=C(O)C=C(O[Si](C)(C)C)C=C3C=C2O1	2809.6	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,2TMS,isomer #3	CC1=CC(=O)C2=C(O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C=C2O1	2852.9	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,3TMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3C=C2O1	2824.2	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,1TBDMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(O)C=C(O)C=C3C=C2O1	3051.8	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,1TBDMS,isomer #2	CC1=CC(=O)C2=C(O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C=C2O1	3069.3	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,1TBDMS,isomer #3	CC1=CC(=O)C2=C(O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C=C2O1	3088.8	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,2TBDMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3C=C2O1	3221.0	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,2TBDMS,isomer #2	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3C=C2O1	3264.3	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,2TBDMS,isomer #3	CC1=CC(=O)C2=C(O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C=C2O1	3266.9	Semi standard non polar	33892256
5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one,3TBDMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3C=C2O1	3536.6	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 - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0190000000-0dce2c5ac354252b7d53	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one GC-MS (3 TMS) - 70eV, Positive	splash10-0zfr-3103900000-a2e6c757c4b56351c29c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 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 - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 10V, Positive-QTOF	splash10-0a4i-0090000000-f92d6ec7c4d98d26dd6b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 20V, Positive-QTOF	splash10-0a4i-0090000000-32cb3a5e6df25365c3e0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 40V, Positive-QTOF	splash10-014i-2490000000-bec0b667498971df8016	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 10V, Negative-QTOF	splash10-0a4i-0090000000-c442d6741172b5739471	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 20V, Negative-QTOF	splash10-0a4i-0090000000-06b07525a411df4dace3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 40V, Negative-QTOF	splash10-014j-4790000000-0677cbd101b4c8565de3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 10V, Negative-QTOF	splash10-0a4i-0090000000-5c99e00473c8f7c5ab03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 20V, Negative-QTOF	splash10-0a4i-0090000000-5c99e00473c8f7c5ab03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 40V, Negative-QTOF	splash10-0a4i-0190000000-023f2fc0e75f15cf3fbb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 10V, Positive-QTOF	splash10-0a4i-0090000000-adb7dbccff647a617461	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 20V, Positive-QTOF	splash10-0a4i-0090000000-242fa92e0bd924504335	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one 40V, Positive-QTOF	splash10-066v-0490000000-1539ab98dc7ecec0a2c7	2021-09-23	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

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320218

PDB ID

Not Available

ChEBI ID

81264

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 5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one (HMDB0033911)

MOL for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

3D MOL for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

3D SDF for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

3D-SDF for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

PDB for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

3D PDB for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

SMILES for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

INCHI for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

Structure for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

3D Structure for HMDB0033911 (5,6,8-Trihydroxy-2-methylbenzo[g]chromen-4-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra