Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:07:18 UTC

Update Date

2022-03-07 02:56:16 UTC

HMDB ID

HMDB0039616

Secondary Accession Numbers

HMDB39616

Metabolite Identification

Common Name

Orientalone

Description

Orientalone 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). Orientalone has been detected, but not quantified in, fruits. This could make orientalone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Orientalone.

Structure

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

HMDB0039616
     RDKit          3D
Orientalone
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.0613    0.9992   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4618   -0.1824    0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507   -0.5088   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -1.5416   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -1.9035   -1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.8884   -1.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.1283   -0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663   -1.4573   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -0.6824   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -1.1262   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454    0.3873    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7951    1.2223    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    1.1345    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478    2.2190    1.5363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    0.7251    0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    1.7969    1.3763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.0402    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0125    0.2737    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    1.2574    1.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985    1.0739   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.9024    0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0919    1.0530    0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572   -2.1215   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175   -2.3125   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655   -0.5598   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725   -2.2158   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -1.2058   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5176    1.0293   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    2.1520    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.3821    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.2662    1.7719 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18  3  1  0
 17  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
M  END


  Mrv0541 05061311172D          

 19 20  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
    0.7145   -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
    2.1434    1.2375    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    2.1434   -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
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  2  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19  3  1  0  0  0  0
 19 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039616

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=O)C2=C(C(O)=C(C(C)=O)C(C)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O5/c1-6-4-8-9(16)5-10(19-3)13(17)12(8)14(18)11(6)7(2)15/h4-5,18H,1-3H3

> <INCHI_KEY>
RRQIDDGRIQVTGM-UHFFFAOYSA-N

> <FORMULA>
C14H12O5

> <MOLECULAR_WEIGHT>
260.2421

> <EXACT_MASS>
260.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.781953802182148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-acetyl-8-hydroxy-2-methoxy-6-methyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.155991245

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.147221838453449

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.124987842035988

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6996489253594076

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
70.3267

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-acetyl-8-hydroxy-2-methoxy-6-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039616
     RDKit          3D
Orientalone
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.0613    0.9992   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4618   -0.1824    0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507   -0.5088   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -1.5416   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -1.9035   -1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.8884   -1.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.1283   -0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663   -1.4573   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -0.6824   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -1.1262   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454    0.3873    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7951    1.2223    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    1.1345    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478    2.2190    1.5363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    0.7251    0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    1.7969    1.3763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.0402    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0125    0.2737    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    1.2574    1.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985    1.0739   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.9024    0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0919    1.0530    0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572   -2.1215   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175   -2.3125   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655   -0.5598   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725   -2.2158   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -1.2058   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5176    1.0293   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    2.1520    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.3821    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.2662    1.7719 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18  3  1  0
 17  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   19                                                            
CONECT    4    6    8                                                       
CONECT    5    9   10                                                       
CONECT    6    1    4   11                                                  
CONECT    7    2   11   15                                                  
CONECT    8    4    9   12                                                  
CONECT    9    5    8   16                                                  
CONECT   10    5   13   19                                                  
CONECT   11    6    7   14                                                  
CONECT   12    8   13   14                                                  
CONECT   13   10   12   17                                                  
CONECT   14   11   12   18                                                  
CONECT   15    7                                                            
CONECT   16    9                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    3   10                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0039616
HETATM    1  C1  UNL     1       5.061   0.999  -0.174  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.462  -0.182   0.258  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.151  -0.509  -0.073  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.897  -1.542  -0.847  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.550  -1.904  -1.206  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.284  -2.888  -1.946  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.415  -1.128  -0.718  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.866  -1.457  -1.049  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.919  -0.682  -0.555  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.275  -1.126  -0.965  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.745   0.387   0.239  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.795   1.222   0.774  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.244   1.135   0.596  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.448   2.219   1.536  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.400   0.725   0.581  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.242   1.797   1.376  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.637  -0.040   0.094  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.013   0.274   0.420  1.00  0.00           C  
HETATM   19  O5  UNL     1       2.265   1.257   1.158  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.099   1.074  -1.299  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.537   1.902   0.205  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.092   1.053   0.250  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.757  -2.121  -1.211  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.018  -2.312  -1.686  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.665  -0.560  -1.840  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.173  -2.216  -1.328  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.000  -1.206  -0.167  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.518   1.029  -0.463  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.725   2.152   0.877  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.687   0.382   1.281  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.499   2.266   1.772  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   23
CONECT    5    6    6    7
CONECT    7    8    8   17
CONECT    8    9   24
CONECT    9   10   11   11
CONECT   10   25   26   27
CONECT   11   12   15
CONECT   12   13   14   14
CONECT   13   28   29   30
CONECT   15   16   17   17
CONECT   16   31
CONECT   17   18
CONECT   18   19   19
END

HMDB0039616
     RDKit          3D
Orientalone
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.0613    0.9992   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4618   -0.1824    0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507   -0.5088   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -1.5416   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504   -1.9035   -1.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2843   -2.8884   -1.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -1.1283   -0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663   -1.4573   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9192   -0.6824   -0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747   -1.1262   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454    0.3873    0.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7951    1.2223    0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2445    1.1345    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4478    2.2190    1.5363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    0.7251    0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    1.7969    1.3763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.0402    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0125    0.2737    0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    1.2574    1.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985    1.0739   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.9024    0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0919    1.0530    0.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572   -2.1215   -1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0175   -2.3125   -1.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6655   -0.5598   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725   -2.2158   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -1.2058   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5176    1.0293   -0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    2.1520    0.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6865    0.3821    1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4992    2.2662    1.7719 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  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18  3  1  0
 17  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  8 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Acetyl-8-hydroxy-2-methoxy-6-methyl-1,4-naphthoquinone	HMDB

Chemical Formula

C₁₄H₁₂O₅

Average Molecular Weight

260.2421

Monoisotopic Molecular Weight

260.068473494

IUPAC Name

7-acetyl-8-hydroxy-2-methoxy-6-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

7-acetyl-8-hydroxy-2-methoxy-6-methylnaphthalene-1,4-dione

CAS Registry Number

64756-97-4

SMILES

COC1=CC(=O)C2=C(C(O)=C(C(C)=O)C(C)=C2)C1=O

InChI Identifier

InChI=1S/C14H12O5/c1-6-4-8-9(16)5-10(19-3)13(17)12(8)14(18)11(6)7(2)15/h4-5,18H,1-3H3

InChI Key

RRQIDDGRIQVTGM-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
Acetophenone
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
Vinylogous ester
Vinylogous acid
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

Extracellular (HMDB: HMDB0039616)
Cytoplasm (HMDB: HMDB0039616)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039616)

Source

Exogenous

Exogenous (HMDB: HMDB0039616)

Food

Food (HMDB: HMDB0039616)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0039616)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039616)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 - 192 °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	0.2 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.16	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.33 m³·mol⁻¹	ChemAxon
Polarizability	25.78 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]+	161.19	31661259
DarkChem	[M-H]-	162.376	31661259
DeepCCS	[M+H]+	163.384	30932474
DeepCCS	[M-H]-	161.026	30932474
DeepCCS	[M-2H]-	193.912	30932474
DeepCCS	[M+Na]+	169.478	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.6	32859911
AllCCS	[M+NH4]+	160.8	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	160.3	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	160.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.09 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2176 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2325.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	392.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	229.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	101.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	479.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	746.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1134.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	468.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1487.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	443.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	459.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	276.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	109.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Orientalone	COC1=CC(=O)C2=C(C(O)=C(C(C)=O)C(C)=C2)C1=O	3170.0	Standard polar	33892256
Orientalone	COC1=CC(=O)C2=C(C(O)=C(C(C)=O)C(C)=C2)C1=O	1997.3	Standard non polar	33892256
Orientalone	COC1=CC(=O)C2=C(C(O)=C(C(C)=O)C(C)=C2)C1=O	2203.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Orientalone,1TMS,isomer #1	COC1=CC(=O)C2=CC(C)=C(C(C)=O)C(O[Si](C)(C)C)=C2C1=O	2307.6	Semi standard non polar	33892256
Orientalone,1TBDMS,isomer #1	COC1=CC(=O)C2=CC(C)=C(C(C)=O)C(O[Si](C)(C)C(C)(C)C)=C2C1=O	2544.0	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 - Orientalone GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-0390000000-aed6414aff1b1ae8dffe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orientalone GC-MS (1 TMS) - 70eV, Positive	splash10-01bi-3195000000-f272ef15a26f0b24e413	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orientalone 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 - Orientalone 10V, Positive-QTOF	splash10-03di-0090000000-855c955de913ffdcf2d6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 20V, Positive-QTOF	splash10-03di-0290000000-dd3f4e05c008656e053d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 40V, Positive-QTOF	splash10-052r-9730000000-4c5d75ea4bc966acbde5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 10V, Negative-QTOF	splash10-0a4i-0090000000-1a2d625656821d0fabaa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 20V, Negative-QTOF	splash10-0a4i-0090000000-3ae81a957e7b86bbed63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 40V, Negative-QTOF	splash10-0api-5950000000-9038df29ffc997973f60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 10V, Negative-QTOF	splash10-0a4i-0090000000-c08b8e182fe1967078f6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 20V, Negative-QTOF	splash10-0a4i-0090000000-fe99581d87453ea80eec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 40V, Negative-QTOF	splash10-004i-1920000000-c8824ef888a5e8dab331	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 10V, Positive-QTOF	splash10-03di-0090000000-ab4f5b92324aa4a99b88	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 20V, Positive-QTOF	splash10-01ox-0090000000-a9c0ad537cddb76a3deb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orientalone 40V, Positive-QTOF	splash10-004i-1950000000-4e072b0e6e56ca1f17cd	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019244

KNApSAcK ID

C00055261

Chemspider ID

10408882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12742405

PDB ID

Not Available

ChEBI ID

174392

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 Orientalone (HMDB0039616)

MOL for HMDB0039616 (Orientalone)

3D MOL for HMDB0039616 (Orientalone)

3D SDF for HMDB0039616 (Orientalone)

3D-SDF for HMDB0039616 (Orientalone)

PDB for HMDB0039616 (Orientalone)

3D PDB for HMDB0039616 (Orientalone)

SMILES for HMDB0039616 (Orientalone)

INCHI for HMDB0039616 (Orientalone)

Structure for HMDB0039616 (Orientalone)

3D Structure for HMDB0039616 (Orientalone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra