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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:36:53 UTC

Update Date

2022-03-07 02:55:43 UTC

HMDB ID

HMDB0038322

Secondary Accession Numbers

HMDB38322

Metabolite Identification

Common Name

4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one

Description

4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one has been detected, but not quantified in, fruits. This could make 4-(3,4-dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one.

Structure

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

HMDB0038322
     RDKit          3D
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one
 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.7201    2.9140    0.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7751    2.0818    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    2.4327   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    3.7445   -0.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    1.5426   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371    0.1740    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -0.7584    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -0.4667   -0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3072   -1.2285   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -1.0066   -1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3824   -0.0293   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142    0.1936   -1.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529    0.7180    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.7081    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5065    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700   -2.0686    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332   -2.4519    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.5049    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -1.8977    1.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567   -0.9760    1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665    0.3206    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872    0.6942    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -0.2004    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110    4.1190   -1.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830    1.8426   -0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -1.9991   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.5960   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992   -0.3467   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112    1.8983    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332    1.0960    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228   -2.8037    0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -3.4595    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380   -2.9443    1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650   -1.2963    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662    1.0477    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  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  1  0
 13 15  2  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  2  1  0
 23  6  2  0
 15  8  1  0
 23 18  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

  Mrv0541 05061310232D          

 23 26  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    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    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
    2.1434    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
    2.8579    0.0000    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
    1.4289    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   -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
    1.4289    2.4750    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  3  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  2  0  0  0  0
 17  9  2  0  0  0  0
 18 10  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038322

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=CC3=C2C(=CC=C3)C1=O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O4/c20-15-7-5-11(8-16(15)21)12-6-4-10-2-1-3-13-18(10)14(12)9-17(22)19(13)23/h1-9,20-22H

> <INCHI_KEY>
ZNAZPYKRTNDUEJ-UHFFFAOYSA-N

> <FORMULA>
C19H12O4

> <MOLECULAR_WEIGHT>
304.2962

> <EXACT_MASS>
304.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.352231738700908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,4-dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.4279932869999996

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.546333391685156

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.774205379031736

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648611279792445

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
88.33459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,4-dihydroxyphenyl)-2-hydroxyphenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038322
     RDKit          3D
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one
 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.7201    2.9140    0.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7751    2.0818    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    2.4327   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    3.7445   -0.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    1.5426   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371    0.1740    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -0.7584    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -0.4667   -0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3072   -1.2285   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -1.0066   -1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3824   -0.0293   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142    0.1936   -1.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529    0.7180    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.7081    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5065    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700   -2.0686    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332   -2.4519    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.5049    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -1.8977    1.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567   -0.9760    1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665    0.3206    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872    0.6942    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -0.2004    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110    4.1190   -1.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830    1.8426   -0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -1.9991   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.5960   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992   -0.3467   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112    1.8983    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332    1.0960    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228   -2.8037    0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -3.4595    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380   -2.9443    1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650   -1.2963    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662    1.0477    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  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  1  0
 13 15  2  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  2  1  0
 23  6  2  0
 15  8  1  0
 23 18  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   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  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   10                                                       
CONECT    3    1   13                                                       
CONECT    4    6   10                                                       
CONECT    5    7   11                                                       
CONECT    6    4   12                                                       
CONECT    7    5   15                                                       
CONECT    8   11   16                                                       
CONECT    9   14   17                                                       
CONECT   10    2    4   18                                                  
CONECT   11    5    8   12                                                  
CONECT   12    6   11   14                                                  
CONECT   13    3   18   19                                                  
CONECT   14    9   12   18                                                  
CONECT   15    7   16   20                                                  
CONECT   16    8   15   21                                                  
CONECT   17    9   19   22                                                  
CONECT   18   10   13   14                                                  
CONECT   19   13   17   23                                                  
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   19                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0038322
HETATM    1  O1  UNL     1      -3.720   2.914   0.052  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.775   2.082   0.055  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.410   2.433  -0.295  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.098   3.744  -0.656  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.425   1.543  -0.287  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.737   0.174   0.087  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.272  -0.758   0.096  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.668  -0.467  -0.211  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.307  -1.228  -1.187  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.639  -1.007  -1.507  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.382  -0.029  -0.878  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.714   0.194  -1.197  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.753   0.718   0.081  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.454   1.708   0.739  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.409   0.507   0.416  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.070  -2.069   0.455  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.333  -2.452   0.791  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.361  -1.505   0.784  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.644  -1.898   1.123  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.657  -0.976   1.114  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.367   0.321   0.767  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.087   0.694   0.433  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.043  -0.200   0.430  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.311   4.119  -1.577  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.583   1.843  -0.566  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.730  -1.999  -1.686  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.141  -1.596  -2.264  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.199  -0.347  -1.901  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.411   1.898   0.537  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.933   1.096   1.181  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.723  -2.804   0.462  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.613  -3.459   1.071  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.838  -2.944   1.396  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.665  -1.296   1.384  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.166   1.048   0.760  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4    5    5
CONECT    4   24
CONECT    5    6   25
CONECT    6    7   23   23
CONECT    7    8   16   16
CONECT    8    9    9   15
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   13
CONECT   12   28
CONECT   13   14   15   15
CONECT   14   29
CONECT   15   30
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   23
CONECT   19   20   20   33
CONECT   20   21   34
CONECT   21   22   22   35
CONECT   22   23
END

HMDB0038322
     RDKit          3D
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one
 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.7201    2.9140    0.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7751    2.0818    0.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4097    2.4327   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    3.7445   -0.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    1.5426   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371    0.1740    0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2725   -0.7584    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6676   -0.4667   -0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3072   -1.2285   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -1.0066   -1.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3824   -0.0293   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7142    0.1936   -1.1968 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7529    0.7180    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.7081    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    0.5065    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700   -2.0686    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332   -2.4519    0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.5049    0.7842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -1.8977    1.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6567   -0.9760    1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665    0.3206    0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872    0.6942    0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -0.2004    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3110    4.1190   -1.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830    1.8426   -0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7297   -1.9991   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1412   -1.5960   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992   -0.3467   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4112    1.8983    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332    1.0960    1.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228   -2.8037    0.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -3.4595    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380   -2.9443    1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650   -1.2963    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662    1.0477    0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  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  1  0
 13 15  2  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  2  1  0
 23  6  2  0
 15  8  1  0
 23 18  1  0
  4 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₂O₄

Average Molecular Weight

304.2962

Monoisotopic Molecular Weight

304.073558872

IUPAC Name

4-(3,4-dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one

Traditional Name

4-(3,4-dihydroxyphenyl)-2-hydroxyphenalen-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=CC3=C2C(=CC=C3)C1=O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C19H12O4/c20-15-7-5-11(8-16(15)21)12-6-4-10-2-1-3-13-18(10)14(12)9-17(22)19(13)23/h1-9,20-22H

InChI Key

ZNAZPYKRTNDUEJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Phenalen-1-one
Phenalen
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Ketone
Enol
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038322)
Cell membrane (HMDB: HMDB0038322)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038322)

Source

Exogenous

Exogenous (HMDB: HMDB0038322)

Food

Food (HMDB: HMDB0038322)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0038322)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038322)

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	0.0085 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.43	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.33 m³·mol⁻¹	ChemAxon
Polarizability	31.35 Å³	ChemAxon
Number of Rings	4	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]+	179.711	30932474
DeepCCS	[M-H]-	177.353	30932474
DeepCCS	[M-2H]-	211.235	30932474
DeepCCS	[M+Na]+	186.462	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	167.8	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.5	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	171.9	32859911
AllCCS	[M+HCOO]-	170.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one	OC1=CC2=C(C=CC3=C2C(=CC=C3)C1=O)C1=CC(O)=C(O)C=C1	4735.1	Standard polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one	OC1=CC2=C(C=CC3=C2C(=CC=C3)C1=O)C1=CC(O)=C(O)C=C1	2972.4	Standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one	OC1=CC2=C(C=CC3=C2C(=CC=C3)C1=O)C1=CC(O)=C(O)C=C1	3309.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C(O)=C2)C1=O	3351.6	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)=CC=C1O	3376.2	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C1O	3412.9	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C)C(O)=C2)C1=O	3333.6	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,2TMS,isomer #2	C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C(O[Si](C)(C)C)=C2)C1=O	3299.9	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C1O[Si](C)(C)C	3297.4	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C1=O	3229.0	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C(O)=C2)C1=O	3606.3	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)=CC=C1O	3614.7	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C1O	3655.4	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C1=O	3814.0	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C1=O	3782.4	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O)=CC2=C43)C=C1O[Si](C)(C)C(C)(C)C	3808.0	Semi standard non polar	33892256
4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=CC=CC3=CC=C2C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C1=O	3912.7	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 - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-0091000000-d88629b283e95a60ccdf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one GC-MS (3 TMS) - 70eV, Positive	splash10-05fs-4000940000-60a5d9441b9b30e27620	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-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 - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 10V, Positive-QTOF	splash10-0a4i-0009000000-66ab770560dcff2d4938	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 20V, Positive-QTOF	splash10-0a4i-0259000000-50448d90f327370d6d32	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 40V, Positive-QTOF	splash10-006t-1190000000-2b6a19b66fda82b38690	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 10V, Negative-QTOF	splash10-0udi-0009000000-9a7ee21347c6dc841014	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 20V, Negative-QTOF	splash10-0udi-0019000000-671ecc0e5281c740540b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 40V, Negative-QTOF	splash10-0002-0191000000-4edd674fcd838cdf9c63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 10V, Positive-QTOF	splash10-0a4i-0009000000-65f36650821dd11e29ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 20V, Positive-QTOF	splash10-0a4i-0029000000-1941a680170ca6c58c43	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 40V, Positive-QTOF	splash10-0002-0090000000-5b455220494f51872381	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 10V, Negative-QTOF	splash10-0udi-0009000000-dee7626e8c41931932f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 20V, Negative-QTOF	splash10-0udi-0049000000-6c95cdd474b64711d880	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one 40V, Negative-QTOF	splash10-00r2-0290000000-fcd7da39a68e99825ca9	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

FDB017657

KNApSAcK ID

Not Available

Chemspider ID

9067299

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10892036

PDB ID

Not Available

ChEBI ID

174908

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 4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one (HMDB0038322)

MOL for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

3D MOL for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

3D SDF for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

3D-SDF for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

PDB for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

3D PDB for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

SMILES for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

INCHI for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

Structure for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

3D Structure for HMDB0038322 (4-(3,4-Dihydroxyphenyl)-2-hydroxy-1H-phenalen-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra