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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:38:08 UTC

Update Date

2022-11-23 21:48:33 UTC

HMDB ID

HMDB0249144

Secondary Accession Numbers

None

Metabolite Identification

Common Name

beta-Naphthoflavone

Description

beta-Naphthoflavone, also known as 5,6-benzoflavone or beta-NF, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Based on a literature review a significant number of articles have been published on beta-Naphthoflavone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Beta-naphthoflavone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically beta-Naphthoflavone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249144
     RDKit          3D
beta-naphthoflavone
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.0080   -0.6139   -2.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5299   -0.3506   -1.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -0.3345   -1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -0.0500   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -0.0193   -0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -0.2728   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506   -0.2365   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225    0.0554    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    0.3139    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    0.2739    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    0.2002    0.8417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    0.2093    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532    0.4867    2.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    0.4891    2.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2851    0.2133    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497    0.2184    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3607   -0.0546   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026   -0.3366   -1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -0.3454   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -0.0715   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -0.0769   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.5473   -2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.5035   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205   -0.4353   -1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8064    0.0824    0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498    0.5413    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8880    0.4788    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    0.7004    2.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666    0.7107    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    0.4414    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4520   -0.0473   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2692   -0.5497   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -0.5696   -2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 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  2  1  0
 10  5  1  0
 21 12  1  0
 20 15  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

2361
  Mrv0541 02241213002D          

 21 24  0  0  0  0            999 V2000
    4.5391   -0.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5487    1.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9911    0.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766   -0.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5391    0.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9911   -0.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055   -0.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9778    1.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4562    0.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0788   -0.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7186    2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4628    1.6727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -1.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -0.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3691   -2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -1.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  8  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  2  0  0  0  0
  7 12  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
 11 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249144

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C=C(OC2=C1C1=CC=CC=C1C=C2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H

> <INCHI_KEY>
OUGIDAPQYNCXRA-UHFFFAOYSA-N

> <FORMULA>
C19H12O2

> <MOLECULAR_WEIGHT>
272.2974

> <EXACT_MASS>
272.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.902777266846385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-1H-benzo[f]chromen-1-one

> <ALOGPS_LOGP>
4.72

> <JCHEM_LOGP>
3.956861855333333

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.421028040399342

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3650204320857435

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
83.42140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-NF

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249144
     RDKit          3D
beta-naphthoflavone
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.0080   -0.6139   -2.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5299   -0.3506   -1.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -0.3345   -1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -0.0500   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -0.0193   -0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -0.2728   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506   -0.2365   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225    0.0554    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    0.3139    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    0.2739    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    0.2002    0.8417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    0.2093    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532    0.4867    2.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    0.4891    2.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2851    0.2133    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497    0.2184    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3607   -0.0546   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026   -0.3366   -1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -0.3454   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -0.0715   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -0.0769   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.5473   -2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.5035   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205   -0.4353   -1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8064    0.0824    0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498    0.5413    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8880    0.4788    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    0.7004    2.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666    0.7107    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    0.4414    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4520   -0.0473   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2692   -0.5497   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -0.5696   -2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 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  2  1  0
 10  5  1  0
 21 12  1  0
 20 15  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2361                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       8.473  -1.625   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.491   3.101   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.850   0.738   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.183   1.508   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.850  -0.802   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.517   0.738   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.473   1.561   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.078  -0.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.183  -1.572   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.517  -0.802   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.159   3.112   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.078   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.918   1.518   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -1.609   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.541   3.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.931   3.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.411  -0.844   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.753  -3.149   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -1.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.422  -3.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.086  -3.160   0.000  0.00  0.00           C+0
CONECT    1    5    8                                                       
CONECT    2    7                                                            
CONECT    3    4    5    7                                                  
CONECT    4    3    6   11                                                  
CONECT    5    1    3    9                                                  
CONECT    6    4   10   13                                                  
CONECT    7    2    3   12                                                  
CONECT    8    1   12   14                                                  
CONECT    9    5   10                                                       
CONECT   10    6    9                                                       
CONECT   11    4   15                                                       
CONECT   12    7    8                                                       
CONECT   13    6   16                                                       
CONECT   14    8   17   18                                                  
CONECT   15   11   16                                                       
CONECT   16   13   15                                                       
CONECT   17   14   19                                                       
CONECT   18   14   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0249144
HETATM    1  O1  UNL     1      -1.008  -0.614  -2.571  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.530  -0.351  -1.468  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.864  -0.335  -1.390  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.498  -0.050  -0.197  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.949  -0.019  -0.057  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.763  -0.273  -1.109  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.151  -0.236  -0.947  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.723   0.055   0.276  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.892   0.314   1.349  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.509   0.274   1.171  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.742   0.200   0.842  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.549   0.209   0.869  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.253   0.487   2.022  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.610   0.489   2.022  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.285   0.213   0.865  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.650   0.218   0.875  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.361  -0.055  -0.270  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.703  -0.337  -1.442  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.300  -0.345  -1.468  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.611  -0.072  -0.319  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.226  -0.077  -0.331  1.00  0.00           C  
HETATM   22  H1  UNL     1       1.426  -0.547  -2.274  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.371  -0.504  -2.076  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.820  -0.435  -1.772  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.806   0.082   0.397  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.350   0.541   2.302  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.888   0.479   2.022  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.710   0.700   2.919  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.167   0.711   2.943  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.198   0.441   1.802  1.00  0.00           H  
HETATM   31  H10 UNL     1      -6.452  -0.047  -0.248  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.269  -0.550  -2.336  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.871  -0.570  -2.401  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4    4   22
CONECT    4    5   11
CONECT    5    6    6   10
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   27
CONECT   11   12
CONECT   12   13   13   21
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   20
CONECT   16   17   17   30
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   20   33
CONECT   20   21   21
END

HMDB0249144
     RDKit          3D
beta-naphthoflavone
 33 36  0  0  0  0  0  0  0  0999 V2000
   -1.0080   -0.6139   -2.5713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5299   -0.3506   -1.4680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645   -0.3345   -1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983   -0.0500   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -0.0193   -0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -0.2728   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506   -0.2365   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7225    0.0554    0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8918    0.3139    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092    0.2739    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    0.2002    0.8417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    0.2093    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2532    0.4867    2.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    0.4891    2.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2851    0.2133    0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497    0.2184    0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3607   -0.0546   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7026   -0.3366   -1.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2996   -0.3454   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -0.0715   -0.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -0.0769   -0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -0.5473   -2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3713   -0.5035   -2.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8205   -0.4353   -1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8064    0.0824    0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3498    0.5413    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8880    0.4788    2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7103    0.7004    2.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1666    0.7107    2.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983    0.4414    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4520   -0.0473   -0.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2692   -0.5497   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707   -0.5696   -2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  4 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 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  2  1  0
 10  5  1  0
 21 12  1  0
 20 15  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Phenyl-1H-naphtho(2,1-b)pyran-1-one	ChEBI
5,6-Benzoflavone	ChEBI
Benzo[F]flavone	ChEBI
beta-NF	ChEBI
b-NF	Generator
Β-NF	Generator
b-Naphthoflavone	Generator
Β-naphthoflavone	Generator
beta Naphthoflavone	MeSH
5,6 Benzoflavone	MeSH

Chemical Formula

C₁₉H₁₂O₂

Average Molecular Weight

272.2974

Monoisotopic Molecular Weight

272.083729628

IUPAC Name

3-phenyl-1H-benzo[f]chromen-1-one

Traditional Name

β-NF

CAS Registry Number

Not Available

SMILES

O=C1C=C(OC2=C1C1=CC=CC=C1C=C2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H12O2/c20-16-12-18(14-7-2-1-3-8-14)21-17-11-10-13-6-4-5-9-15(13)19(16)17/h1-12H

InChI Key

OUGIDAPQYNCXRA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

Flavone
Naphthopyran
Chromone
Benzopyran
Naphthalene
1-benzopyran
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:77013 )
extended flavonoid (CHEBI:77013 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	4.72	ALOGPS
logP	3.96	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	15.42	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.42 m³·mol⁻¹	ChemAxon
Polarizability	29.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.987	30932474
DeepCCS	[M-H]-	161.629	30932474
DeepCCS	[M-2H]-	194.516	30932474
DeepCCS	[M+Na]+	170.081	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.9	32859911
AllCCS	[M+Na]+	168.9	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-naphthoflavone	O=C1C=C(OC2=C1C1=CC=CC=C1C=C2)C1=CC=CC=C1	3872.3	Standard polar	33892256
beta-naphthoflavone	O=C1C=C(OC2=C1C1=CC=CC=C1C=C2)C1=CC=CC=C1	2749.9	Standard non polar	33892256
beta-naphthoflavone	O=C1C=C(OC2=C1C1=CC=CC=C1C=C2)C1=CC=CC=C1	2874.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - beta-Naphthoflavone EI-B (Non-derivatized)	splash10-00di-3790000000-c4fd2800aec22c1db180	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Naphthoflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fkc-0790000000-6973081d9045c7da2cb3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Naphthoflavone 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone LC-ESI-QFT 19V, positive-QTOF	splash10-00di-0090000000-477b182a3d98acf7c8de	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone LC-ESI-IT 19V, positive-QTOF	splash10-00di-0290000000-1f9bc8406f696b71df06	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 45V, Positive-QTOF	splash10-00di-0190000000-863bf53ef62dd32e063d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 60V, Positive-QTOF	splash10-00di-0970000000-e5a269713a88ebf44b9a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 30V, Positive-QTOF	splash10-00di-0090000000-e25cd9fc2b116584b9e6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 15V, Positive-QTOF	splash10-00di-0090000000-3de2c4fa53a326a7e3b1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 75V, Positive-QTOF	splash10-0gdi-0910000000-5dbe6ecdef26345d0ea6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 90V, Positive-QTOF	splash10-016r-0910000000-30f4cc55a4b512a2aef8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - beta-Naphthoflavone 75V, Positive-QTOF	splash10-0gdi-0910000000-cd088658b2f6c7befc12	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 10V, Positive-QTOF	splash10-00di-0090000000-010a3b305c25e462a79b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 20V, Positive-QTOF	splash10-00di-0090000000-de9a5e205bd25fffc710	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 40V, Positive-QTOF	splash10-0fkc-2920000000-bde412f668d00610a16a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 10V, Negative-QTOF	splash10-00di-0090000000-5ef2149861a8dc3f9c1d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 20V, Negative-QTOF	splash10-00di-0090000000-c5419f0cc24661074af8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 40V, Negative-QTOF	splash10-0v6u-0920000000-1fdf409f56dc2a3ca1f1	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 10V, Positive-QTOF	splash10-00di-0090000000-c145c134e7a1d3427f27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 20V, Positive-QTOF	splash10-00di-0090000000-c145c134e7a1d3427f27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 40V, Positive-QTOF	splash10-006t-0390000000-f2d5baa5be6c114a05f7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 10V, Negative-QTOF	splash10-00di-0090000000-61c6e7d71c517d8f7271	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 20V, Negative-QTOF	splash10-00di-0090000000-61c6e7d71c517d8f7271	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Naphthoflavone 40V, Negative-QTOF	splash10-00r6-0490000000-9890ca1e6f57c8471cc8	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06732

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2271

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Beta-Naphthoflavone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

77013

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1223231

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for beta-Naphthoflavone (HMDB0249144)

MOL for HMDB0249144 (beta-Naphthoflavone)

3D MOL for HMDB0249144 (beta-Naphthoflavone)

3D SDF for HMDB0249144 (beta-Naphthoflavone)

3D-SDF for HMDB0249144 (beta-Naphthoflavone)

PDB for HMDB0249144 (beta-Naphthoflavone)

3D PDB for HMDB0249144 (beta-Naphthoflavone)

SMILES for HMDB0249144 (beta-Naphthoflavone)

INCHI for HMDB0249144 (beta-Naphthoflavone)

Structure for HMDB0249144 (beta-Naphthoflavone)

3D Structure for HMDB0249144 (beta-Naphthoflavone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra