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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:51:04 UTC

Update Date

2022-03-07 02:56:11 UTC

HMDB ID

HMDB0039405

Secondary Accession Numbers

HMDB39405

Metabolite Identification

Common Name

3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one

Description

3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-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. 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-CD]pyran-1-one has been detected, but not quantified in, fruits. This could make 3-hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-CD]pyran-1-one a potential biomarker for the consumption of these foods.

Structure

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

HMDB0039405
     RDKit          3D
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one
 34 37  0  0  0  0  0  0  0  0999 V2000
   -4.0952   -2.4277    0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -1.7638    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -2.3230    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -1.6712   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990   -2.0083   -1.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792   -0.2058    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    0.5751    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -0.0221    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.8297    0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6207   -1.3746    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731   -1.1146   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -1.6485   -0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647   -0.3125   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984    0.2255   -1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.9520    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    2.5860    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057    1.8149    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2614    2.4070    0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4361    1.6943    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3238    0.3285    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -0.2943    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098    0.4135    0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897   -2.1094    0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -2.1501   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7722   -1.0276    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0237   -2.0074    1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410   -1.1054   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4700   -0.1170   -2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    0.8598   -1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587    2.5354    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    3.6670    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887    3.5055    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    2.2049    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2301   -0.2564    0.1979 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  1  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
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061311062D          

 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  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039405

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1OC(=O)C2=CC=CC3=C2C1=C(C=C3)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O4/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/h1-9,18-19,21H

> <INCHI_KEY>
LIFGUYJSGKEZDL-UHFFFAOYSA-N

> <FORMULA>
C18H12O4

> <MOLECULAR_WEIGHT>
292.2855

> <EXACT_MASS>
292.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.76502818338587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.496862936666666

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.717344577968719

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.78813924967368

> <JCHEM_PKA_STRONGEST_BASIC>
-4.239035526661286

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
81.23509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039405
     RDKit          3D
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one
 34 37  0  0  0  0  0  0  0  0999 V2000
   -4.0952   -2.4277    0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -1.7638    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -2.3230    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -1.6712   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990   -2.0083   -1.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792   -0.2058    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    0.5751    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -0.0221    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.8297    0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6207   -1.3746    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731   -1.1146   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -1.6485   -0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647   -0.3125   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984    0.2255   -1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.9520    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    2.5860    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057    1.8149    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2614    2.4070    0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4361    1.6943    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3238    0.3285    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -0.2943    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098    0.4135    0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897   -2.1094    0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -2.1501   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7722   -1.0276    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0237   -2.0074    1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410   -1.1054   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4700   -0.1170   -2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    0.8598   -1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587    2.5354    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    3.6670    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887    3.5055    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    2.2049    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2301   -0.2564    0.1979 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  1  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
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  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    HMDB0039405
HETATM    1  O1  UNL     1      -4.095  -2.428   0.094  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.025  -1.764   0.082  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.780  -2.323   0.022  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.543  -1.671  -0.005  1.00  0.00           C  
HETATM    5  O3  UNL     1       0.099  -2.008  -1.222  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.679  -0.206   0.062  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.489   0.575   0.043  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.819  -0.022   0.014  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.349  -0.830   0.988  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.621  -1.375   0.850  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.373  -1.115  -0.266  1.00  0.00           C  
HETATM   12  O4  UNL     1       5.659  -1.649  -0.436  1.00  0.00           O  
HETATM   13  C9  UNL     1       3.865  -0.313  -1.247  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.598   0.226  -1.102  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.334   1.952   0.084  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.872   2.586   0.142  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.006   1.815   0.161  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.261   2.407   0.214  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.436   1.694   0.230  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.324   0.329   0.188  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.095  -0.294   0.134  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.910   0.414   0.120  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.090  -2.109   0.798  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.560  -2.150  -1.942  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.772  -1.028   1.890  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.024  -2.007   1.622  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.441  -1.105  -0.087  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.470  -0.117  -2.119  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.204   0.860  -1.884  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.259   2.535   0.067  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.974   3.667   0.174  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.289   3.506   0.246  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.385   2.205   0.273  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.230  -0.256   0.198  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4
CONECT    4    5    6   23
CONECT    5   24
CONECT    6    7   22   22
CONECT    7    8   15   15
CONECT    8    9    9   14
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   13
CONECT   12   27
CONECT   13   14   14   28
CONECT   14   29
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   22
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21   34
CONECT   21   22
END

HMDB0039405
     RDKit          3D
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one
 34 37  0  0  0  0  0  0  0  0999 V2000
   -4.0952   -2.4277    0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -1.7638    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7804   -2.3230    0.0221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -1.6712   -0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990   -2.0083   -1.2219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792   -0.2058    0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    0.5751    0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -0.0221    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.8297    0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6207   -1.3746    0.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731   -1.1146   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6595   -1.6485   -0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647   -0.3125   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984    0.2255   -1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3339    1.9520    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8725    2.5860    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0057    1.8149    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2614    2.4070    0.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4361    1.6943    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3238    0.3285    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -0.2943    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098    0.4135    0.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897   -2.1094    0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -2.1501   -1.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7722   -1.0276    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0237   -2.0074    1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4410   -1.1054   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4700   -0.1170   -2.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    0.8598   -1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2587    2.5354    0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    3.6670    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2887    3.5055    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3848    2.2049    0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2301   -0.2564    0.1979 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  1  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
  4 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₂O₄

Average Molecular Weight

292.2855

Monoisotopic Molecular Weight

292.073558872

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1OC(=O)C2=CC=CC3=C2C1=C(C=C3)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H12O4/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/h1-9,18-19,21H

InChI Key

LIFGUYJSGKEZDL-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: HMDB0039405)

Cellular substructure

Membrane (HMDB: HMDB0039405)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039405)

Source

Exogenous

Food

Food (HMDB: HMDB0039405)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0039405)

Not Available

Nutrient (HMDB: HMDB0039405)

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	0.017 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.5	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.24 m³·mol⁻¹	ChemAxon
Polarizability	29.77 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]+	166.122	31661259
DarkChem	[M-H]-	166.078	31661259
DeepCCS	[M+H]+	175.884	30932474
DeepCCS	[M-H]-	173.526	30932474
DeepCCS	[M-2H]-	207.308	30932474
DeepCCS	[M+Na]+	182.534	30932474
AllCCS	[M+H]+	168.2	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	171.6	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	170.3	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	168.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one	OC1OC(=O)C2=CC=CC3=C2C1=C(C=C3)C1=CC=C(O)C=C1	4595.4	Standard polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one	OC1OC(=O)C2=CC=CC3=C2C1=C(C=C3)C1=CC=C(O)C=C1	2904.1	Standard non polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one	OC1OC(=O)C2=CC=CC3=C2C1=C(C=C3)C1=CC=C(O)C=C1	3180.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one,1TMS,isomer #1	C[Si](C)(C)OC1OC(=O)C2=C3C1=C(C1=CC=C(O)C=C1)C=CC3=CC=C2	3171.4	Semi standard non polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)OC(O)C2=C43)C=C1	3137.4	Semi standard non polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)OC(O[Si](C)(C)C)C2=C43)C=C1	3074.5	Semi standard non polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1OC(=O)C2=C3C1=C(C1=CC=C(O)C=C1)C=CC3=CC=C2	3410.2	Semi standard non polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)OC(O)C2=C43)C=C1	3370.9	Semi standard non polar	33892256
3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC=C3C=CC=C4C(=O)OC(O[Si](C)(C)C(C)(C)C)C2=C43)C=C1	3554.6	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 - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0090000000-090654b5a52a552d3725	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-7009200000-515337c6e43104835621	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-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 - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 10V, Positive-QTOF	splash10-0006-0090000000-9d5aa7aaafd2fc7b5356	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 20V, Positive-QTOF	splash10-00mn-0090000000-2c3c5e3ac7797b745567	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 40V, Positive-QTOF	splash10-014j-0390000000-1bc598757ad3732a690a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 10V, Negative-QTOF	splash10-0006-0090000000-f91a2052c9b10acca272	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 20V, Negative-QTOF	splash10-0002-0090000000-f8ba4a2dc85d6ab4c7e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 40V, Negative-QTOF	splash10-00kb-1090000000-1b4e0b300fbb6bc64b84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 10V, Negative-QTOF	splash10-0006-0090000000-d71fe0d59e8a306109af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 20V, Negative-QTOF	splash10-0006-0090000000-bc7befa6229aa97e4c4c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 40V, Negative-QTOF	splash10-014i-0090000000-4bc82979e170b9621454	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 10V, Positive-QTOF	splash10-0006-0090000000-be50a384be69f6afb13f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 20V, Positive-QTOF	splash10-0007-0090000000-a8ba7b37cfb939563feb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one 40V, Positive-QTOF	splash10-0002-0090000000-9536192aeb1a893c19ed	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

FDB018980

KNApSAcK ID

Not Available

Chemspider ID

9208825

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11033651

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 3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one (HMDB0039405)

MOL for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

3D MOL for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

3D SDF for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

3D-SDF for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

PDB for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

3D PDB for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

SMILES for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

INCHI for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

Structure for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

3D Structure for HMDB0039405 (3-Hydroxy-4-(4-hydroxyphenyl)-1H,3H-naphtho[1,8-cd]pyran-1-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra