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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:46:11 UTC

Update Date

2022-03-07 02:56:53 UTC

HMDB ID

HMDB0041120

Secondary Accession Numbers

HMDB41120

Metabolite Identification

Common Name

4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione

Description

4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione, also known as 2-phenylnaphthalic anhydride or CH3CH2OOH, belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-phenyl-1H,3H-naphtho[1,8-CD]pyran-1,3-dione has been detected, but not quantified in, fruits. This could make 4-phenyl-1H,3H-naphtho[1,8-CD]pyran-1,3-dione a potential biomarker for the consumption of these foods.

Structure

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

HMDB0041120
     RDKit          3D
4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione
 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.0103    3.5154   -0.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    2.6005   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059    2.8192   -0.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    1.7790   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    1.9748   -0.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    0.4763   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407   -0.5386    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737   -0.4263   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -0.2464   -1.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128   -0.1325   -1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719   -0.2051   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2476   -0.3851    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798   -0.4913    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -1.7776    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -1.9812    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.9196    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -1.1650    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.1500    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    1.0913    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    1.2993   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    0.3061    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1935   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.0124   -2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -0.1155   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.4408    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -0.6330    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -2.5702    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -2.9498    1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528   -2.1326    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5308   -0.3243    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7076    1.9037   -0.0167 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
 12 13  2  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
 21  6  2  0
 13  8  1  0
 21 16  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END


  Mrv0541 05061312242D          

 21 24  0  0  0  0            999 V2000
    1.4289   -4.1250    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   -3.7125    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
    2.1434   -2.8875    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
    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   -0.4125    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   -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
    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
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 15 12  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 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041120

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1OC(=O)C2=C(C=CC3=C2C1=CC=C3)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H10O3/c19-17-14-8-4-7-12-9-10-13(11-5-2-1-3-6-11)16(15(12)14)18(20)21-17/h1-10H

> <INCHI_KEY>
ISOSGRNBACDIEA-UHFFFAOYSA-N

> <FORMULA>
C18H10O3

> <MOLECULAR_WEIGHT>
274.2702

> <EXACT_MASS>
274.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.085311878687406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
4.059285761

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.869055010319952

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
78.95139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041120
     RDKit          3D
4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione
 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.0103    3.5154   -0.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    2.6005   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059    2.8192   -0.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    1.7790   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    1.9748   -0.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    0.4763   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407   -0.5386    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737   -0.4263   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -0.2464   -1.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128   -0.1325   -1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719   -0.2051   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2476   -0.3851    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798   -0.4913    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -1.7776    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -1.9812    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.9196    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -1.1650    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.1500    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    1.0913    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    1.2993   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    0.3061    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1935   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.0124   -2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -0.1155   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.4408    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -0.6330    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -2.5702    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -2.9498    1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528   -2.1326    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5308   -0.3243    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7076    1.9037   -0.0167 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
 12 13  2  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
 21  6  2  0
 13  8  1  0
 21 16  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       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       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    7    8                                                       
CONECT    5    2   11                                                       
CONECT    6    3   11                                                       
CONECT    7    4   12                                                       
CONECT    8    4   14                                                       
CONECT    9   10   12                                                       
CONECT   10    9   13                                                       
CONECT   11    5    6   13                                                  
CONECT   12    7    9   15                                                  
CONECT   13   10   11   16                                                  
CONECT   14    8   15   17                                                  
CONECT   15   12   14   16                                                  
CONECT   16   13   15   18                                                  
CONECT   17   14   19   21                                                  
CONECT   18   16   20   21                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0041120
HETATM    1  O1  UNL     1      -3.010   3.515  -0.654  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.153   2.600  -0.481  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.806   2.819  -0.680  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.098   1.779  -0.477  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.338   1.975  -0.654  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.358   0.476  -0.064  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.541  -0.539   0.140  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.974  -0.426  -0.108  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.464  -0.246  -1.374  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.813  -0.133  -1.620  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.672  -0.205  -0.546  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.248  -0.385   0.754  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.880  -0.491   0.926  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.019  -1.778   0.558  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.321  -1.981   0.755  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.182  -0.920   0.530  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.528  -1.165   0.746  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.460  -0.150   0.551  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.017   1.091   0.144  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.655   1.299  -0.062  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.729   0.306   0.125  1.00  0.00           C  
HETATM   22  H1  UNL     1       1.789  -0.194  -2.232  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.194   0.012  -2.645  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.728  -0.115  -0.741  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.944  -0.441   1.597  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.562  -0.633   1.958  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.743  -2.570   0.717  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.695  -2.950   1.077  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.853  -2.133   1.061  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.531  -0.324   0.716  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.708   1.904  -0.017  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   21   21
CONECT    7    8   14   14
CONECT    8    9    9   13
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   26
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   21
CONECT   17   18   18   29
CONECT   18   19   30
CONECT   19   20   20   31
CONECT   20   21
END

HMDB0041120
     RDKit          3D
4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione
 31 34  0  0  0  0  0  0  0  0999 V2000
   -3.0103    3.5154   -0.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    2.6005   -0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059    2.8192   -0.6801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977    1.7790   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    1.9748   -0.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    0.4763   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407   -0.5386    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737   -0.4263   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -0.2464   -1.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128   -0.1325   -1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6719   -0.2051   -0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2476   -0.3851    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8798   -0.4913    0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -1.7776    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3215   -1.9812    0.7545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.9196    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5276   -1.1650    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.1500    0.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0170    1.0913    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552    1.2993   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    0.3061    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1935   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    0.0124   -2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7282   -0.1155   -0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9439   -0.4408    1.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -0.6330    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -2.5702    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6949   -2.9498    1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8528   -2.1326    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5308   -0.3243    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7076    1.9037   -0.0167 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
 12 13  2  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
 21  6  2  0
 13  8  1  0
 21 16  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Phenylnaphthalic anhydride	HMDB
CH3CH2OOH	HMDB
Ethyl hydroperoxide	HMDB
Hydroperoxide, ethyl	HMDB

Chemical Formula

C₁₈H₁₀O₃

Average Molecular Weight

274.2702

Monoisotopic Molecular Weight

274.062994186

IUPAC Name

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

Traditional Name

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

CAS Registry Number

56252-04-1

SMILES

O=C1OC(=O)C2=C(C=CC3=C2C1=CC=C3)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H10O3/c19-17-14-8-4-7-12-9-10-13(11-5-2-1-3-6-11)16(15(12)14)18(20)21-17/h1-10H

InChI Key

ISOSGRNBACDIEA-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: HMDB0041120)

Cellular substructure

Membrane (HMDB: HMDB0041120)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041120)

Source

Exogenous

Food

Food (HMDB: HMDB0041120)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0041120)

Not Available

Nutrient (HMDB: HMDB0041120)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	241 - 243 °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	0.00059 g/L	ALOGPS
logP	3.84	ALOGPS
logP	4.06	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.95 m³·mol⁻¹	ChemAxon
Polarizability	28.09 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]+	163.466	31661259
DarkChem	[M-H]-	160.74	31661259
DeepCCS	[M+H]+	165.886	30932474
DeepCCS	[M-H]-	163.528	30932474
DeepCCS	[M-2H]-	196.848	30932474
DeepCCS	[M+Na]+	172.075	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	158.9	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	164.2	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione	O=C1OC(=O)C2=C(C=CC3=C2C1=CC=C3)C1=CC=CC=C1	4261.0	Standard polar	33892256
4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione	O=C1OC(=O)C2=C(C=CC3=C2C1=CC=C3)C1=CC=CC=C1	2652.8	Standard non polar	33892256
4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione	O=C1OC(=O)C2=C(C=CC3=C2C1=CC=C3)C1=CC=CC=C1	2771.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-0090000000-e89dc867ec9f02225d4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 10V, Positive-QTOF	splash10-004i-0090000000-3caca8ebe30a4411431d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 20V, Positive-QTOF	splash10-0059-0090000000-799426161e35a3450ee6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 40V, Positive-QTOF	splash10-001i-2190000000-c6b4bc2f3a416e7fd1ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 10V, Negative-QTOF	splash10-00di-0090000000-6b49bce198e6423ed72d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 20V, Negative-QTOF	splash10-00di-0090000000-e94892d00f74a4ff2dcf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 40V, Negative-QTOF	splash10-00di-0090000000-bd267284f24a33d79e83	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 10V, Negative-QTOF	splash10-00di-0090000000-86e2ec1f4e4fbb3bbea2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 20V, Negative-QTOF	splash10-00di-0090000000-86e2ec1f4e4fbb3bbea2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 40V, Negative-QTOF	splash10-00di-0090000000-c7114c15ac4cb5f477cd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 10V, Positive-QTOF	splash10-004i-0090000000-9b88e591128a669efd3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 20V, Positive-QTOF	splash10-004i-0090000000-9b88e591128a669efd3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione 40V, Positive-QTOF	splash10-001i-0090000000-ffd75d37f471f22ccbed	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

FDB021002

KNApSAcK ID

Not Available

Chemspider ID

9992823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11818168

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 4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione (HMDB0041120)

MOL for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

3D MOL for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

3D SDF for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

3D-SDF for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

PDB for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

3D PDB for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

SMILES for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

INCHI for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

Structure for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

3D Structure for HMDB0041120 (4-Phenyl-1H,3H-naphtho[1,8-cd]pyran-1,3-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra