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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:08:58 UTC

Update Date

2022-03-07 02:57:01 UTC

HMDB ID

HMDB0041462

Secondary Accession Numbers

HMDB41462

Metabolite Identification

Common Name

2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

Description

2-Hydroxy-4-(4-methoxyphenyl)-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. 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one has been detected, but not quantified in, fruits. This could make 2-hydroxy-4-(4-methoxyphenyl)-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 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one.

Structure

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

HMDB0041462
     RDKit          3D
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
 37 40  0  0  0  0  0  0  0  0999 V2000
    6.0032    0.6424    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3007    0.0167    0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.1922   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    0.2113    1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.0139    0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370   -0.6439   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -0.9004   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -2.2075   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -2.4817   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256   -1.4838   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.8049   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2251   -0.8017   -0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    0.4937   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    0.7902   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.1871   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.1211   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.4998    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    2.4485    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    3.7543    0.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9955    2.1740    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    3.0925    0.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432   -1.0569   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3981   -0.8323   -1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2483    2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0991    0.4413    0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9092    1.7394    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705    0.7025    1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665    0.3159    1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193   -3.0115   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942   -3.5074   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428   -2.8477   -0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746   -1.0559   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4943    1.3182   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    1.7247    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    4.0295    1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.5683   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -1.1672   -1.9429 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 16  7  1  0
 15 10  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 19 35  1  0
 22 36  1  0
 23 37  1  0
M  END


  Mrv0541 05061312412D          

 23 26  0  0  0  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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    0.8250    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    2.4750    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
    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
    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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  4  2  0  0  0  0
 17 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 11  2  0  0  0  0
 19 13  2  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
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 20 18  1  0  0  0  0
 21 18  1  0  0  0  0
 22 20  2  0  0  0  0
 23  1  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041462

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O3/c1-23-14-8-5-12(6-9-14)15-10-7-13-3-2-4-16-19(13)17(15)11-18(21)20(16)22/h2-11,21H,1H3

> <INCHI_KEY>
PVZKBQMWQRUUFI-UHFFFAOYSA-N

> <FORMULA>
C20H14O3

> <MOLECULAR_WEIGHT>
302.3234

> <EXACT_MASS>
302.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.47045858281963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.877452664666666

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.41944302430023

> <JCHEM_PKA_STRONGEST_BASIC>
-3.60819562117108

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
90.83599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-(4-methoxyphenyl)phenalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041462
     RDKit          3D
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
 37 40  0  0  0  0  0  0  0  0999 V2000
    6.0032    0.6424    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3007    0.0167    0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.1922   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    0.2113    1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.0139    0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370   -0.6439   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -0.9004   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -2.2075   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -2.4817   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256   -1.4838   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.8049   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2251   -0.8017   -0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    0.4937   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    0.7902   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.1871   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.1211   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.4998    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    2.4485    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    3.7543    0.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9955    2.1740    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    3.0925    0.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432   -1.0569   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3981   -0.8323   -1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2483    2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0991    0.4413    0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9092    1.7394    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705    0.7025    1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665    0.3159    1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193   -3.0115   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942   -3.5074   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428   -2.8477   -0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746   -1.0559   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4943    1.3182   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    1.7247    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    4.0295    1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.5683   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -1.1672   -1.9429 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 16  7  1  0
 15 10  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 19 35  1  0
 22 36  1  0
 23 37  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   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   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   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    4                                                       
CONECT    3    2   13                                                       
CONECT    4    2   16                                                       
CONECT    5    8   12                                                       
CONECT    6    9   12                                                       
CONECT    7   10   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11   17   18                                                       
CONECT   12    5    6   15                                                  
CONECT   13    3    7   19                                                  
CONECT   14    8    9   23                                                  
CONECT   15   10   12   17                                                  
CONECT   16    4   19   20                                                  
CONECT   17   11   15   19                                                  
CONECT   18   11   20   21                                                  
CONECT   19   13   16   17                                                  
CONECT   20   16   18   22                                                  
CONECT   21   18                                                            
CONECT   22   20                                                            
CONECT   23    1   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0041462
HETATM    1  C1  UNL     1       6.003   0.642   1.056  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.301   0.017   0.024  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.949  -0.192  -0.009  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.120   0.211   1.015  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.773  -0.014   0.949  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.237  -0.644  -0.138  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.206  -0.900  -0.262  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.632  -2.207  -0.438  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.973  -2.482  -0.517  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.926  -1.484  -0.425  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.287  -1.805  -0.513  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.225  -0.802  -0.424  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.795   0.494  -0.250  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.453   0.790  -0.166  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.481  -0.187  -0.250  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.112   0.121  -0.167  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.669   1.500   0.008  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.580   2.449   0.090  1.00  0.00           C  
HETATM   19  O2  UNL     1      -1.085   3.754   0.258  1.00  0.00           O  
HETATM   20  C18 UNL     1      -2.995   2.174   0.012  1.00  0.00           C  
HETATM   21  O3  UNL     1      -3.827   3.092   0.093  1.00  0.00           O  
HETATM   22  C19 UNL     1       2.043  -1.057  -1.174  1.00  0.00           C  
HETATM   23  C20 UNL     1       3.398  -0.832  -1.111  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.731   0.248   2.076  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.099   0.441   0.872  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.909   1.739   1.076  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.570   0.702   1.854  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.167   0.316   1.784  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.119  -3.012  -0.513  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.294  -3.507  -0.654  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.543  -2.848  -0.649  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.275  -1.056  -0.492  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.494   1.318  -0.175  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.400   1.725   0.056  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.605   4.029   1.105  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.614  -1.568  -2.058  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.022  -1.167  -1.943  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   22
CONECT    7    8    8   16
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   15
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15   20
CONECT   15   16   16
CONECT   16   17
CONECT   17   18   18   34
CONECT   18   19   20
CONECT   19   35
CONECT   20   21   21
CONECT   22   23   23   36
CONECT   23   37
END

HMDB0041462
     RDKit          3D
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
 37 40  0  0  0  0  0  0  0  0999 V2000
    6.0032    0.6424    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3007    0.0167    0.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.1922   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    0.2113    1.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734   -0.0139    0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370   -0.6439   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -0.9004   -0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -2.2075   -0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -2.4817   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256   -1.4838   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.8049   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2251   -0.8017   -0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7950    0.4937   -0.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4531    0.7902   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.1871   -0.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.1211   -0.1669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.4998    0.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5804    2.4485    0.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    3.7543    0.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9955    2.1740    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8267    3.0925    0.0928 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0432   -1.0569   -1.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3981   -0.8323   -1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7308    0.2483    2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0991    0.4413    0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9092    1.7394    1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5705    0.7025    1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665    0.3159    1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193   -3.0115   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942   -3.5074   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428   -2.8477   -0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746   -1.0559   -0.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4943    1.3182   -0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    1.7247    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    4.0295    1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.5683   -2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -1.1672   -1.9429 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 16  7  1  0
 15 10  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 19 35  1  0
 22 36  1  0
 23 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₁₄O₃

Average Molecular Weight

302.3234

Monoisotopic Molecular Weight

302.094294314

IUPAC Name

2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one

Traditional Name

2-hydroxy-4-(4-methoxyphenyl)phenalen-1-one

CAS Registry Number

159853-36-8

SMILES

COC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23

InChI Identifier

InChI=1S/C20H14O3/c1-23-14-8-5-12(6-9-14)15-10-7-13-3-2-4-16-19(13)17(15)11-18(21)20(16)22/h2-11,21H,1H3

InChI Key

PVZKBQMWQRUUFI-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
Anisole
Phenoxy compound
Phenol ether
Aryl ketone
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Ketone
Ether
Enol
Organic oxygen compound
Organooxygen compound
Organic oxide
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: HMDB0041462)
Cell membrane (HMDB: HMDB0041462)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041462)

Source

Exogenous

Exogenous (HMDB: HMDB0041462)

Food

Food (HMDB: HMDB0041462)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041462)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041462)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	222 - 223 °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	0.0011 g/L	ALOGPS
logP	3.72	ALOGPS
logP	3.88	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.84 m³·mol⁻¹	ChemAxon
Polarizability	32.47 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-2H]-	207.201	30932474
DeepCCS	[M+Na]+	182.428	30932474
AllCCS	[M+H]+	172.2	32859911
AllCCS	[M+H-H2O]+	168.6	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.5	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	173.7	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.	8.45 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6927 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2594.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	509.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	268.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	713.5 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	649.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1490.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	576.4 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	1494.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	472.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	494.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	433.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	373.5 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	17.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one	COC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23	4215.4	Standard polar	33892256
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one	COC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23	2862.9	Standard non polar	33892256
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one	COC1=CC=C(C=C1)C1=C2C=C(O)C(=O)C3=CC=CC(C=C1)=C23	3094.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,1TMS,isomer #1	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O[Si](C)(C)C)=CC2=C43)C=C1	3221.4	Semi standard non polar	33892256
2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one,1TBDMS,isomer #1	COC1=CC=C(C2=CC=C3C=CC=C4C(=O)C(O[Si](C)(C)C(C)(C)C)=CC2=C43)C=C1	3438.4	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 - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0091000000-7748df75d77686b7ad9e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8019000000-f75efe318e2b5699df03	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-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 - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Positive-QTOF	splash10-0udi-0009000000-8b30f7f532857ef6405c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Positive-QTOF	splash10-0ufr-1195000000-8dc43bf5107b3942a706	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Positive-QTOF	splash10-0f89-1190000000-08c35f24d98e7f68cdab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Negative-QTOF	splash10-0udi-0009000000-4a75a68ed8021b91cd71	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Negative-QTOF	splash10-0udi-0029000000-a124a509b4de80bca597	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Negative-QTOF	splash10-052r-1090000000-d8ef7fbe93e1da9fa210	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Negative-QTOF	splash10-0udi-0009000000-e692d58cc60b5b612091	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Negative-QTOF	splash10-0udi-0029000000-4265326d6f5887479d46	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Negative-QTOF	splash10-00di-0190000000-2cd5ef46f38dd2f0392c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 10V, Positive-QTOF	splash10-0udi-0009000000-c9aaaf24c55736f7a8a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 20V, Positive-QTOF	splash10-0udi-0009000000-c9aaaf24c55736f7a8a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one 40V, Positive-QTOF	splash10-053r-0090000000-1771bd54df1d6fd413b8	2021-09-24	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

FDB021419

KNApSAcK ID

C00055689

Chemspider ID

553916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

638391

PDB ID

Not Available

ChEBI ID

Not Available

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 2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one (HMDB0041462)

MOL for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D MOL for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D SDF for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D-SDF for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

PDB for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D PDB for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

SMILES for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

INCHI for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

Structure for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

3D Structure for HMDB0041462 (2-Hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra