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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:46:14 UTC

Update Date

2022-03-07 02:56:53 UTC

HMDB ID

HMDB0041121

Secondary Accession Numbers

HMDB41121

Metabolite Identification

Common Name

2-(4-Hydroxyphenyl)naphthalic anhydride

Description

2-(4-Hydroxyphenyl)naphthalic anhydride 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-(4-Hydroxyphenyl)naphthalic anhydride is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(4-hydroxyphenyl)naphthalic anhydride has been detected, but not quantified in, fruits. This could make 2-(4-hydroxyphenyl)naphthalic anhydride a potential biomarker for the consumption of these foods.

Structure

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

HMDB0041121
     RDKit          3D
2-(4-Hydroxyphenyl)naphthalic anhydride
 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.3080   -2.7695    2.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4521   -2.0274    1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -2.3719    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.5430    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559   -1.8044    1.0740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845   -0.3527    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212    0.4915   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306    0.1705   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6264    0.9697    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.7200    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4204   -0.3651   -0.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7900   -0.6779   -0.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -1.1863   -1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2065   -0.9006   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248    1.6366   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    1.9565   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547    1.1159   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6958    1.4040   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    0.5893    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988   -0.5440    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727   -0.8385    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -0.0127    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.8342    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6968    1.3541    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026   -0.1554   -0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242   -2.0517   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5507   -1.5795   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335    2.2398   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    2.8563   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464    2.2827   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6892    0.7592    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -1.1998    1.1963 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
  4  5  2  0
  4  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  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 14  8  1  0
 22 17  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv0541 05061312242D          

 22 25  0  0  0  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
    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
    1.4289   -4.1250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    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
    2.8579   -2.4750    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  1  2  0  0  0  0
  3  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  6  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 12  1  0  0  0  0
 20 17  2  0  0  0  0
 21 18  2  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041121

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=C2C(=O)OC(=O)C3=CC=CC(C=C1)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H10O4/c19-12-7-4-10(5-8-12)13-9-6-11-2-1-3-14-15(11)16(13)18(21)22-17(14)20/h1-9,19H

> <INCHI_KEY>
YFQUGKAERRJRCN-UHFFFAOYSA-N

> <FORMULA>
C18H10O4

> <MOLECULAR_WEIGHT>
290.2696

> <EXACT_MASS>
290.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.11714213615511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(4-hydroxyphenyl)-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.7557204393333325

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.669485729839913

> <JCHEM_PKA_STRONGEST_BASIC>
-5.493456126121264

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
80.93229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(4-hydroxyphenyl)-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041121
     RDKit          3D
2-(4-Hydroxyphenyl)naphthalic anhydride
 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.3080   -2.7695    2.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4521   -2.0274    1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -2.3719    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.5430    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559   -1.8044    1.0740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845   -0.3527    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212    0.4915   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306    0.1705   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6264    0.9697    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.7200    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4204   -0.3651   -0.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7900   -0.6779   -0.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -1.1863   -1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2065   -0.9006   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248    1.6366   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    1.9565   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547    1.1159   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6958    1.4040   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    0.5893    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988   -0.5440    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727   -0.8385    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -0.0127    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.8342    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6968    1.3541    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026   -0.1554   -0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242   -2.0517   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5507   -1.5795   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335    2.2398   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    2.8563   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464    2.2827   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6892    0.7592    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -1.1998    1.1963 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
  4  5  2  0
  4  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  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 14  8  1  0
 22 17  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   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       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -4.620   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       2.667  -7.700   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1   11                                                       
CONECT    3    1   14                                                       
CONECT    4    7   10                                                       
CONECT    5    8   10                                                       
CONECT    6    9   11                                                       
CONECT    7    4   12                                                       
CONECT    8    5   12                                                       
CONECT    9    6   13                                                       
CONECT   10    4    5   13                                                  
CONECT   11    2    6   15                                                  
CONECT   12    7    8   19                                                  
CONECT   13    9   10   16                                                  
CONECT   14    3   15   17                                                  
CONECT   15   11   14   16                                                  
CONECT   16   13   15   18                                                  
CONECT   17   14   20   22                                                  
CONECT   18   16   21   22                                                  
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0041121
HETATM    1  O1  UNL     1      -3.308  -2.770   2.061  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.452  -2.027   1.511  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.112  -2.372   1.618  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.179  -1.543   1.006  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.056  -1.804   1.074  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.584  -0.353   0.274  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.321   0.491  -0.338  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.731   0.170  -0.334  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.626   0.970   0.334  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.980   0.720   0.306  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.420  -0.365  -0.417  1.00  0.00           C  
HETATM   12  O4  UNL     1       5.790  -0.678  -0.488  1.00  0.00           O  
HETATM   13  C9  UNL     1       3.550  -1.186  -1.099  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.207  -0.901  -1.044  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.125   1.637  -1.023  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.451   1.956  -1.112  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.355   1.116  -0.506  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.696   1.404  -0.568  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.636   0.589   0.034  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.199  -0.544   0.715  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.873  -0.839   0.783  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.951  -0.013   0.173  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.327   1.834   0.916  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.697   1.354   0.837  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.503  -0.155  -0.037  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.924  -2.052  -1.673  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.551  -1.579  -1.604  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.633   2.240  -1.467  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.753   2.856  -1.654  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.046   2.283  -1.094  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.689   0.759   0.020  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.908  -1.200   1.196  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   22   22
CONECT    7    8   15   15
CONECT    8    9    9   14
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   13
CONECT   12   25
CONECT   13   14   14   26
CONECT   14   27
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   18   22
CONECT   18   19   19   30
CONECT   19   20   31
CONECT   20   21   21   32
CONECT   21   22
END

HMDB0041121
     RDKit          3D
2-(4-Hydroxyphenyl)naphthalic anhydride
 32 35  0  0  0  0  0  0  0  0999 V2000
   -3.3080   -2.7695    2.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4521   -2.0274    1.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117   -2.3719    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.5430    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0559   -1.8044    1.0740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5845   -0.3527    0.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212    0.4915   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7306    0.1705   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6264    0.9697    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.7200    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4204   -0.3651   -0.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7900   -0.6779   -0.4883 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5503   -1.1863   -1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2065   -0.9006   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1248    1.6366   -1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    1.9565   -1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547    1.1159   -0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6958    1.4040   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6362    0.5893    0.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988   -0.5440    0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727   -0.8385    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9507   -0.0127    0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.8342    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6968    1.3541    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026   -0.1554   -0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242   -2.0517   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5507   -1.5795   -1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335    2.2398   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7531    2.8563   -1.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464    2.2827   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6892    0.7592    0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9076   -1.1998    1.1963 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
  4  5  2  0
  4  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  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  2  1  0
 22  6  2  0
 14  8  1  0
 22 17  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₀O₄

Average Molecular Weight

290.2696

Monoisotopic Molecular Weight

290.057908808

IUPAC Name

6-(4-hydroxyphenyl)-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione

Traditional Name

6-(4-hydroxyphenyl)-3-oxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione

CAS Registry Number

158922-28-2

SMILES

OC1=CC=C(C=C1)C1=C2C(=O)OC(=O)C3=CC=CC(C=C1)=C23

InChI Identifier

InChI=1S/C18H10O4/c19-12-7-4-10(5-8-12)13-9-6-11-2-1-3-14-15(11)16(13)18(21)22-17(14)20/h1-9,19H

InChI Key

YFQUGKAERRJRCN-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

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Phenylnaphthalenes

Direct Parent

Phenylnaphthalenes

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041121)

Cellular substructure

Membrane (HMDB: HMDB0041121)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041121)

Source

Exogenous

Food

Food (HMDB: HMDB0041121)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041121)

Not Available

Nutrient (HMDB: HMDB0041121)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	278 - 281 °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	0.0055 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.76	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.93 m³·mol⁻¹	ChemAxon
Polarizability	29.12 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
DarkChem	[M+H]+	166.25	31661259
DarkChem	[M-H]-	165.642	31661259
DeepCCS	[M-2H]-	197.159	30932474
DeepCCS	[M+Na]+	172.386	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	168.5	32859911
AllCCS	[M+Na-2H]-	167.3	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(4-Hydroxyphenyl)naphthalic anhydride	OC1=CC=C(C=C1)C1=C2C(=O)OC(=O)C3=CC=CC(C=C1)=C23	4625.6	Standard polar	33892256
2-(4-Hydroxyphenyl)naphthalic anhydride	OC1=CC=C(C=C1)C1=C2C(=O)OC(=O)C3=CC=CC(C=C1)=C23	2899.7	Standard non polar	33892256
2-(4-Hydroxyphenyl)naphthalic anhydride	OC1=CC=C(C=C1)C1=C2C(=O)OC(=O)C3=CC=CC(C=C1)=C23	3201.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(4-Hydroxyphenyl)naphthalic anhydride,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)OC(=O)C2=C43)C=C1	3154.5	Semi standard non polar	33892256
2-(4-Hydroxyphenyl)naphthalic anhydride,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)OC(=O)C2=C43)C=C1	3374.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0090000000-cf2266a71aa08769114c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride GC-MS (1 TMS) - 70eV, Positive	splash10-0g4j-3039000000-385b2df583386029d186	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 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-(4-Hydroxyphenyl)naphthalic anhydride 10V, Positive-QTOF	splash10-0006-0090000000-62632854b1b25a5f17b1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 20V, Positive-QTOF	splash10-0007-0090000000-4125b4f3adf7afee1fbb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 40V, Positive-QTOF	splash10-00kb-1090000000-969c98c822978eee695f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 10V, Negative-QTOF	splash10-000i-0090000000-9d2ec3c2855670b5002f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 20V, Negative-QTOF	splash10-0002-0090000000-1f314643695405c2beee	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 40V, Negative-QTOF	splash10-0002-0090000000-bcfb1c567f696dda8e8d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 10V, Negative-QTOF	splash10-000i-0090000000-a7acc8ef53b98f63da71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 20V, Negative-QTOF	splash10-000i-0090000000-a7acc8ef53b98f63da71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 40V, Negative-QTOF	splash10-000i-0090000000-095b51f1e93634f1a381	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 10V, Positive-QTOF	splash10-0006-0090000000-e5a8a7e143c08f6145f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 20V, Positive-QTOF	splash10-0006-0090000000-e5a8a7e143c08f6145f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(4-Hydroxyphenyl)naphthalic anhydride 40V, Positive-QTOF	splash10-01ot-0090000000-e0005e23a4a21cc47b09	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021003

KNApSAcK ID

Not Available

Chemspider ID

8599723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10424295

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-(4-Hydroxyphenyl)naphthalic anhydride (HMDB0041121)

MOL for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

3D MOL for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

3D SDF for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

3D-SDF for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

PDB for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

3D PDB for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

SMILES for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

INCHI for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

Structure for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

3D Structure for HMDB0041121 (2-(4-Hydroxyphenyl)naphthalic anhydride)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra