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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:17:59 UTC

Update Date

2021-09-26 22:56:54 UTC

HMDB ID

HMDB0247291

Secondary Accession Numbers

None

Metabolite Identification

Common Name

alpha-Naphthoflavone

Description

alpha-naphthoflavone, also known as 7,8-benzoflavone or 7,8-BF, 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 alpha-naphthoflavone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpha-naphthoflavone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically alpha-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

HMDB0247291
     RDKit          3D
alpha-Naphthoflavone
 33 36  0  0  0  0  0  0  0  0999 V2000
   -0.0763   -3.7530   -1.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -2.5658   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -1.9615   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105   -0.6673   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -0.0517    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -0.7225    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618   -0.0836    0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.2276    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    1.9046    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    1.2607    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1871    0.0190    0.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -0.5015   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.7937   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983   -2.2834   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775   -1.4530   -0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -0.1597   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634    0.6663   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002    1.9554    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    2.4447    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565    1.6094    0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    0.3154   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -2.5605   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.7397   -0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855   -0.6501    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9403    1.7004    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    2.9260    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    1.7891    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4758   -3.3009   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4814   -1.8120   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4181    0.2422   -0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1545    2.5763    0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    3.4468    0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    1.9762    0.5629 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
 13  2  1  0
 21 16  1  0
 10  5  1  0
 21 12  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
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

BHF
  Mrv0541 02241213262D          

 21 24  0  0  0  0            999 V2000
   -1.2475    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475    2.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4025    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650    1.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8775    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2275    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4025    0.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0100   -0.0424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350   -0.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8350   -1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2475   -2.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -2.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4850   -1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -0.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  2  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247291

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1

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

> <INCHI_KEY>
VFMMPHCGEFXGIP-UHFFFAOYSA-N

> <FORMULA>
C19H12O2

> <MOLECULAR_WEIGHT>
272.2974

> <EXACT_MASS>
272.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.73054105393158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-4H-benzo[h]chromen-4-one

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
3.956861855333333

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.55625270461061

> <JCHEM_PKA_STRONGEST_BASIC>
-5.381708808182734

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
83.42140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-naphthoflavone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0247291
     RDKit          3D
alpha-Naphthoflavone
 33 36  0  0  0  0  0  0  0  0999 V2000
   -0.0763   -3.7530   -1.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -2.5658   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -1.9615   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105   -0.6673   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -0.0517    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -0.7225    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618   -0.0836    0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.2276    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    1.9046    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    1.2607    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1871    0.0190    0.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -0.5015   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.7937   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983   -2.2834   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775   -1.4530   -0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -0.1597   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634    0.6663   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002    1.9554    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    2.4447    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565    1.6094    0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    0.3154   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -2.5605   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.7397   -0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855   -0.6501    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9403    1.7004    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    2.9260    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    1.7891    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4758   -3.3009   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4814   -1.8120   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4181    0.2422   -0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1545    2.5763    0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    3.4468    0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    1.9762    0.5629 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
 13  2  1  0
 21 16  1  0
 10  5  1  0
 21 12  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
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: BHF                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.329   1.255   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.559   2.588   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.329   3.922   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.019   2.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.751   3.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.291   3.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.061   2.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.601   2.588   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.371   1.255   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.601  -0.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.061  -0.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.291   1.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.751   1.255   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.019  -0.079   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.559  -0.079   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.329  -1.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.559  -2.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.329  -4.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.869  -4.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.639  -2.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.869  -1.413   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    7   11   13                                                  
CONECT   13    4   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15    1   14   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0247291
HETATM    1  O1  UNL     1      -0.076  -3.753  -1.282  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.006  -2.566  -0.875  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.201  -1.962  -0.557  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.310  -0.667  -0.111  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.593  -0.052   0.218  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.775  -0.722   0.104  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.962  -0.084   0.432  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.988   1.228   0.876  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.793   1.905   0.991  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.624   1.261   0.663  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.187   0.019   0.013  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.977  -0.501  -0.272  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.142  -1.794  -0.723  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.398  -2.283  -1.007  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.477  -1.453  -0.830  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.347  -0.160  -0.382  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.463   0.666  -0.210  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.300   1.955   0.239  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.043   2.445   0.524  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.956   1.609   0.345  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.097   0.315  -0.104  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.095  -2.561  -0.674  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.834  -1.740  -0.233  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.886  -0.650   0.329  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.940   1.700   1.126  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.813   2.926   1.337  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.669   1.789   0.750  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.476  -3.301  -1.357  1.00  0.00           H  
HETATM   29  H8  UNL     1      -4.481  -1.812  -1.046  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.418   0.242  -0.444  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.155   2.576   0.367  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.891   3.447   0.875  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.967   1.976   0.563  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
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
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   17   21
CONECT   17   18   30
CONECT   18   19   19   31
CONECT   19   20   32
CONECT   20   21   21   33
END

HMDB0247291
     RDKit          3D
alpha-Naphthoflavone
 33 36  0  0  0  0  0  0  0  0999 V2000
   -0.0763   -3.7530   -1.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -2.5658   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013   -1.9615   -0.5573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105   -0.6673   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5935   -0.0517    0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7747   -0.7225    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618   -0.0836    0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.2276    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    1.9046    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    1.2607    0.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1871    0.0190    0.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -0.5015   -0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -1.7937   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983   -2.2834   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4775   -1.4530   -0.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3468   -0.1597   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4634    0.6663   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3002    1.9554    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    2.4447    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565    1.6094    0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966    0.3154   -0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0950   -2.5605   -0.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.7397   -0.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855   -0.6501    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9403    1.7004    1.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    2.9260    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6693    1.7891    0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4758   -3.3009   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4814   -1.8120   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4181    0.2422   -0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1545    2.5763    0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    3.4468    0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9675    1.9762    0.5629 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
 13  2  1  0
 21 16  1  0
 10  5  1  0
 21 12  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
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Phenyl-4H-naphtho(1,2-b)pyran-4-one	ChEBI
7,8-Benzoflavone	ChEBI
7,8-BF	ChEBI
alpha-Naphthylflavone	ChEBI
Benzo[H]flavone	ChEBI
a-Naphthylflavone	Generator
Α-naphthylflavone	Generator
a-Naphthoflavone	Generator
Α-naphthoflavone	Generator
alpha-Naphthoflavone	MeSH

Chemical Formula

C₁₉H₁₂O₂

Average Molecular Weight

272.2974

Monoisotopic Molecular Weight

272.083729628

IUPAC Name

2-phenyl-4H-benzo[h]chromen-4-one

Traditional Name

α-naphthoflavone

CAS Registry Number

Not Available

SMILES

O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:76995 )
extended flavonoid (CHEBI:76995 )
a small molecule (CPD-10550 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	4.73	ALOGPS
logP	3.96	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.56	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	29.73 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-2H]-	194.601	30932474
DeepCCS	[M+Na]+	170.166	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.9	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Naphthoflavone	O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1	3795.3	Standard polar	33892256
alpha-Naphthoflavone	O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1	2771.1	Standard non polar	33892256
alpha-Naphthoflavone	O=C1C=C(OC2=C1C=CC1=CC=CC=C21)C1=CC=CC=C1	2888.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - alpha-Naphthoflavone EI-B (Non-derivatized)	splash10-00di-2950000000-3f3c0aa2d9b942a7e0fd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Naphthoflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fkc-0690000000-d95b19eb4958254ecd16	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-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 - alpha-Naphthoflavone LC-ESI-QTOF , positive-QTOF	splash10-00di-0190000000-aa43a8f9d0352725e676	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Naphthoflavone LC-ESI-QTOF , positive-QTOF	splash10-00di-0090000000-f5d4d77da80ab36ad023	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Positive-QTOF	splash10-00di-0190000000-aa43a8f9d0352725e676	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Positive-QTOF	splash10-00di-0090000000-f5d4d77da80ab36ad023	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Positive-QTOF	splash10-00di-0090000000-f8f5cbed6b1a04c98672	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Positive-QTOF	splash10-00di-0090000000-f2b100cfd0874fb81692	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Positive-QTOF	splash10-0uk9-3930000000-e1b30d3cc6f415020fad	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Negative-QTOF	splash10-00di-0090000000-8c730956d4df5d2c2df1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Negative-QTOF	splash10-00di-0090000000-5390fc715752907dd7b7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Negative-QTOF	splash10-0v4i-0940000000-e6c5d980a7f70c449320	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Positive-QTOF	splash10-00di-0090000000-c145c134e7a1d3427f27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Positive-QTOF	splash10-00di-0090000000-c145c134e7a1d3427f27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Positive-QTOF	splash10-00dj-0290000000-44ff94d129c424a2b412	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 10V, Negative-QTOF	splash10-00di-0090000000-61c6e7d71c517d8f7271	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 20V, Negative-QTOF	splash10-00di-0090000000-61c6e7d71c517d8f7271	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Naphthoflavone 40V, Negative-QTOF	splash10-00dl-0490000000-642128239715b00d3426	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

11297

KEGG Compound ID

Not Available

BioCyc ID

CPD-10550

BiGG ID

Not Available

Wikipedia Link

Alpha-Naphthoflavone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

76995

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1465221

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 alpha-Naphthoflavone (HMDB0247291)

MOL for HMDB0247291 (alpha-Naphthoflavone)

3D MOL for HMDB0247291 (alpha-Naphthoflavone)

3D SDF for HMDB0247291 (alpha-Naphthoflavone)

3D-SDF for HMDB0247291 (alpha-Naphthoflavone)

PDB for HMDB0247291 (alpha-Naphthoflavone)

3D PDB for HMDB0247291 (alpha-Naphthoflavone)

SMILES for HMDB0247291 (alpha-Naphthoflavone)

INCHI for HMDB0247291 (alpha-Naphthoflavone)

Structure for HMDB0247291 (alpha-Naphthoflavone)

3D Structure for HMDB0247291 (alpha-Naphthoflavone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra