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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:12:25 UTC

Update Date

2022-03-07 02:54:26 UTC

HMDB ID

HMDB0035254

Secondary Accession Numbers

HMDB35254

Metabolite Identification

Common Name

7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone

Description

7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone has been detected, but not quantified in, nuts. This could make 7-hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone.

Structure

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

HMDB0035254
     RDKit          3D
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.8466   -0.0194   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9869    0.4457    0.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251    0.2358    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573    1.2947    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4140    2.6723    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    1.0710    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    2.0694    0.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -0.2397    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305   -1.3307    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -2.5947    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2379   -2.7512   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -4.0288   -0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -1.6441   -0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -0.3355   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669    0.8137   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    0.2287   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8232    1.4412    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706   -1.1040    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -2.1162    0.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6539    0.4457   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728    0.2748   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7493   -1.1079   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.4112    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    2.8330   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    2.8895    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -3.4546    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -4.1322   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -1.8520   -0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    1.5111   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4895    1.0881   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274   -0.2819    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026   -0.3871   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.9391    1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    1.1994    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    2.5162    1.1212 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 18  3  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

  Mrv0541 05061308202D          

 19 20  0  0  0  0            999 V2000
    1.4289    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.1434   -0.4125    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
    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
    2.1434    1.2375    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
    2.8579    0.8250    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
    3.5724   -0.4125    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19  4  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035254

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C)C(=O)C2=C(C=C(O)C=C2C1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-7(2)10-5-9(16)6-11-12(10)13(17)8(3)15(19-4)14(11)18/h5-7,16H,1-4H3

> <INCHI_KEY>
GMQGRIMALOVAPW-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.58936601116566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-2-methoxy-3-methyl-5-(propan-2-yl)-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.4254819769999996

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3130691211321

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950304294710508

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
73.4306

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-5-isopropyl-2-methoxy-3-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035254
     RDKit          3D
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.8466   -0.0194   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9869    0.4457    0.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251    0.2358    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573    1.2947    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4140    2.6723    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    1.0710    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    2.0694    0.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -0.2397    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305   -1.3307    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -2.5947    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2379   -2.7512   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -4.0288   -0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -1.6441   -0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -0.3355   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669    0.8137   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    0.2287   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8232    1.4412    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706   -1.1040    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -2.1162    0.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6539    0.4457   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728    0.2748   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7493   -1.1079   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.4112    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    2.8330   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    2.8895    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -3.4546    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -4.1322   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -1.8520   -0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    1.5111   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4895    1.0881   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274   -0.2819    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026   -0.3871   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.9391    1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    1.1994    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    2.5162    1.1212 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 18  3  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4   19                                                            
CONECT    5    9   10                                                       
CONECT    6    9   11                                                       
CONECT    7    1    2   10                                                  
CONECT    8    3   13   15                                                  
CONECT    9    5    6   16                                                  
CONECT   10    5    7   12                                                  
CONECT   11    6   12   14                                                  
CONECT   12   10   11   13                                                  
CONECT   13    8   12   17                                                  
CONECT   14   11   15   18                                                  
CONECT   15    8   14   19                                                  
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    4   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0035254
HETATM    1  C1  UNL     1       4.847  -0.019  -0.344  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.987   0.446   0.679  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.625   0.236   0.481  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.857   1.295   0.346  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.414   2.672   0.401  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.425   1.071   0.135  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.306   2.069   0.005  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.186  -0.240   0.069  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.630  -1.331   0.213  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.106  -2.595   0.153  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.238  -2.751  -0.051  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.775  -4.029  -0.113  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.033  -1.644  -0.191  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.561  -0.336  -0.141  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.467   0.814  -0.281  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.814   0.229  -0.782  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.823   1.441   1.035  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.071  -1.104   0.424  1.00  0.00           C  
HETATM   19  O4  UNL     1       2.813  -2.116   0.555  1.00  0.00           O  
HETATM   20  H1  UNL     1       4.654   0.446  -1.326  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.873   0.275  -0.047  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.749  -1.108  -0.460  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.630   3.411   0.212  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.245   2.833  -0.295  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.830   2.889   1.422  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.756  -3.455   0.268  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.766  -4.132  -0.263  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.101  -1.852  -0.351  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.238   1.511  -1.098  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.490   1.088  -1.059  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.327  -0.282   0.031  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.603  -0.387  -1.653  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.178   0.939   1.816  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.875   1.199   1.363  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.730   2.516   1.121  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5    6
CONECT    5   23   24   25
CONECT    6    7    7    8
CONECT    8    9    9   14
CONECT    9   10   18
CONECT   10   11   11   26
CONECT   11   12   13
CONECT   12   27
CONECT   13   14   14   28
CONECT   14   15
CONECT   15   16   17   29
CONECT   16   30   31   32
CONECT   17   33   34   35
CONECT   18   19   19
END

HMDB0035254
     RDKit          3D
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.8466   -0.0194   -0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9869    0.4457    0.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251    0.2358    0.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573    1.2947    0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4140    2.6723    0.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4249    1.0710    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    2.0694    0.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -0.2397    0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305   -1.3307    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -2.5947    0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2379   -2.7512   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754   -4.0288   -0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -1.6441   -0.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610   -0.3355   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669    0.8137   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    0.2287   -0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8232    1.4412    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0706   -1.1040    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128   -2.1162    0.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6539    0.4457   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728    0.2748   -0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7493   -1.1079   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305    3.4112    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    2.8330   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    2.8895    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7556   -3.4546    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -4.1322   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012   -1.8520   -0.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    1.5111   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4895    1.0881   -1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274   -0.2819    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6026   -0.3871   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    0.9391    1.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    1.1994    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304    2.5162    1.1212 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
  4  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 18  3  1  0
 14  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15-Nor-2-O-methylisohemigossypolone	HMDB
7-H-5-IPM-N	MeSH
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone	MeSH

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

7-hydroxy-2-methoxy-3-methyl-5-(propan-2-yl)-1,4-dihydronaphthalene-1,4-dione

Traditional Name

7-hydroxy-5-isopropyl-2-methoxy-3-methylnaphthalene-1,4-dione

CAS Registry Number

253609-43-7

SMILES

COC1=C(C)C(=O)C2=C(C=C(O)C=C2C1=O)C(C)C

InChI Identifier

InChI=1S/C15H16O4/c1-7(2)10-5-9(16)6-11-12(10)13(17)8(3)15(19-4)14(11)18/h5-7,16H,1-4H3

InChI Key

GMQGRIMALOVAPW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Vinylogous ester
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035254)
Cell membrane (HMDB: HMDB0035254)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035254)

Source

Exogenous

Exogenous (HMDB: HMDB0035254)

Food

Food (HMDB: HMDB0035254)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0035254)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035254)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.14 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.43	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.31	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.43 m³·mol⁻¹	ChemAxon
Polarizability	27.59 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]+	164.516	31661259
DarkChem	[M-H]-	164.274	31661259
DeepCCS	[M+H]+	169.549	30932474
DeepCCS	[M-H]-	167.191	30932474
DeepCCS	[M-2H]-	200.152	30932474
DeepCCS	[M+Na]+	175.642	30932474
AllCCS	[M+H]+	158.2	32859911
AllCCS	[M+H-H2O]+	154.6	32859911
AllCCS	[M+NH4]+	161.6	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	163.8	32859911
AllCCS	[M+Na-2H]-	163.8	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone	COC1=C(C)C(=O)C2=C(C=C(O)C=C2C1=O)C(C)C	3083.4	Standard polar	33892256
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone	COC1=C(C)C(=O)C2=C(C=C(O)C=C2C1=O)C(C)C	2112.4	Standard non polar	33892256
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone	COC1=C(C)C(=O)C2=C(C=C(O)C=C2C1=O)C(C)C	2168.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone,1TMS,isomer #1	COC1=C(C)C(=O)C2=C(C=C(O[Si](C)(C)C)C=C2C(C)C)C1=O	2214.5	Semi standard non polar	33892256
7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone,1TBDMS,isomer #1	COC1=C(C)C(=O)C2=C(C=C(O[Si](C)(C)C(C)(C)C)C=C2C(C)C)C1=O	2420.0	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 - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone GC-MS (Non-derivatized) - 70eV, Positive	splash10-02aj-0390000000-87b45bd0c99bfaa8faf8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone GC-MS (1 TMS) - 70eV, Positive	splash10-01bi-3197000000-5896fc3de9b838ebe8c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 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 - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 10V, Positive-QTOF	splash10-03di-0090000000-d36394a4ff6c9f1d0321	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 20V, Positive-QTOF	splash10-03di-3590000000-520252442a171c8fbed7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 40V, Positive-QTOF	splash10-01p9-2920000000-4eb1d5a5d2ccf0d6af25	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 10V, Negative-QTOF	splash10-0a4i-0090000000-0145f91d8952b7b54fa6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 20V, Negative-QTOF	splash10-0a4i-0090000000-3a695d0cb5595bab271f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 40V, Negative-QTOF	splash10-01q3-3890000000-b14d5def4b51d4bad85e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 10V, Negative-QTOF	splash10-0a4i-0090000000-07597ad49430bb51c246	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 20V, Negative-QTOF	splash10-0a4i-0090000000-0e59212d55925b27c15c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 40V, Negative-QTOF	splash10-0i10-3790000000-6b0b084bb375d898a098	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 10V, Positive-QTOF	splash10-03di-0090000000-3a72f988fa1ed5d11d03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 20V, Positive-QTOF	splash10-03di-0190000000-e26831c2eaf41db1893c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone 40V, Positive-QTOF	splash10-0bti-5890000000-940a74062d73f134988f	2021-09-22	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

FDB013914

KNApSAcK ID

C00057287

Chemspider ID

21377155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86205980

PDB ID

Not Available

ChEBI ID

174420

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 7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone (HMDB0035254)

MOL for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

3D MOL for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

3D SDF for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

3D-SDF for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

PDB for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

3D PDB for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

SMILES for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

INCHI for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

Structure for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

3D Structure for HMDB0035254 (7-Hydroxy-5-isopropyl-2-methoxy-3-methyl-1,4-naphthoquinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra