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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:08:37 UTC

Update Date

2021-09-26 23:10:20 UTC

HMDB ID

HMDB0255496

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nebicapone

Description

Nebicapone, also known as bia 3-202, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review a significant number of articles have been published on Nebicapone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nebicapone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nebicapone 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

HMDB0255496
     RDKit          3D
Nebicapone
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.9698    0.7380   -1.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360    0.2268   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -0.3785    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534   -0.2795    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527   -1.2700   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -1.1858   -0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245   -0.1013   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488    0.8833    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    0.8043    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078    0.2574   -0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    0.8107   -1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    0.8299   -1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781    1.4035   -2.7280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9079    0.2617   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622    0.2103   -0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1649   -0.3154    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.9000    1.5411 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2581   -1.8086    2.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503   -0.4759    1.9269 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7940   -0.2991    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.2389    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -1.3975    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718   -2.1347   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -1.9595   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3829   -0.0223   -0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080    1.7538    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    1.6120    1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766    1.2552   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775    1.4013   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8874    0.5876   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.7464    1.1656 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
  9  4  1  0
 20 10  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
 20 31  1  0
M  CHG  2  17   1  19  -1
M  END


  Mrv1652309112117082D          

 20 21  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
    0.7145   -3.7125    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   -2.4750    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
    2.1434   -3.7125    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    0.8250    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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  CHG  2  18   1  20  -1
M  END
> <DATABASE_ID>
HMDB0255496

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(=CC(=C1O)[N+]([O-])=O)C(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H11NO5/c16-12(6-9-4-2-1-3-5-9)10-7-11(15(19)20)14(18)13(17)8-10/h1-5,7-8,17-18H,6H2

> <INCHI_KEY>
MRFOLGFFTUGAEB-UHFFFAOYSA-N

> <FORMULA>
C14H11NO5

> <MOLECULAR_WEIGHT>
273.244

> <EXACT_MASS>
273.063722458

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.988417588088197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3,4-dihydroxy-5-nitrophenyl)-2-phenylethan-1-one

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.698086700333333

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.338883321480104

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.351915570405451

> <JCHEM_PKA_STRONGEST_BASIC>
-6.465056503372787

> <JCHEM_POLAR_SURFACE_AREA>
100.67

> <JCHEM_REFRACTIVITY>
71.46499999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nebicapone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255496
     RDKit          3D
Nebicapone
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.9698    0.7380   -1.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360    0.2268   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -0.3785    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534   -0.2795    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527   -1.2700   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -1.1858   -0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245   -0.1013   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488    0.8833    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    0.8043    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078    0.2574   -0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    0.8107   -1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    0.8299   -1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781    1.4035   -2.7280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9079    0.2617   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622    0.2103   -0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1649   -0.3154    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.9000    1.5411 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2581   -1.8086    2.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503   -0.4759    1.9269 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7940   -0.2991    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.2389    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -1.3975    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718   -2.1347   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -1.9595   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3829   -0.0223   -0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080    1.7538    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    1.6120    1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766    1.2552   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775    1.4013   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8874    0.5876   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.7464    1.1656 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
  9  4  1  0
 20 10  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
 20 31  1  0
M  CHG  2  17   1  19  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   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       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O-1
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   12   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0255496
HETATM    1  O1  UNL     1       0.970   0.738  -1.665  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.336   0.227  -0.695  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.092  -0.379   0.402  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.553  -0.279   0.170  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.253  -1.270  -0.507  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.608  -1.186  -0.726  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.325  -0.101  -0.275  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.649   0.883   0.394  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.283   0.804   0.619  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.108   0.257  -0.701  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.872   0.811  -1.701  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.266   0.830  -1.688  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.978   1.403  -2.728  1.00  0.00           O  
HETATM   14  C12 UNL     1      -3.908   0.262  -0.611  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.262   0.210  -0.468  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.165  -0.315   0.434  1.00  0.00           C  
HETATM   17  N1  UNL     1      -3.818  -0.900   1.541  1.00  0.00           N1+
HETATM   18  O4  UNL     1      -3.258  -1.809   2.165  1.00  0.00           O  
HETATM   19  O5  UNL     1      -5.050  -0.476   1.927  1.00  0.00           O1-
HETATM   20  C14 UNL     1      -1.794  -0.299   0.356  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.885   0.239   1.323  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.766  -1.398   0.647  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.672  -2.135  -0.865  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.146  -1.960  -1.253  1.00  0.00           H  
HETATM   25  H5  UNL     1       6.383  -0.022  -0.439  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.208   1.754   0.760  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.815   1.612   1.151  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.377   1.255  -2.544  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.977   1.401  -2.689  1.00  0.00           H  
HETATM   30  H10 UNL     1      -5.887   0.588  -1.147  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.222  -0.746   1.166  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   21   22
CONECT    4    5    5    9
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   27
CONECT   10   11   11   20
CONECT   11   12   28
CONECT   12   13   14   14
CONECT   13   29
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   20   20
CONECT   17   18   18   19
CONECT   20   31
END

HMDB0255496
     RDKit          3D
Nebicapone
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.9698    0.7380   -1.6651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3360    0.2268   -0.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -0.3785    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5534   -0.2795    0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527   -1.2700   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077   -1.1858   -0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3245   -0.1013   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488    0.8833    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2834    0.8043    0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1078    0.2574   -0.7012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    0.8107   -1.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    0.8299   -1.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781    1.4035   -2.7280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9079    0.2617   -0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2622    0.2103   -0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1649   -0.3154    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.9000    1.5411 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2581   -1.8086    2.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0503   -0.4759    1.9269 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7940   -0.2991    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8850    0.2389    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7660   -1.3975    0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6718   -2.1347   -0.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -1.9595   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3829   -0.0223   -0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080    1.7538    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8147    1.6120    1.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766    1.2552   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775    1.4013   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8874    0.5876   -1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217   -0.7464    1.1656 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
  9  4  1  0
 20 10  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 13 29  1  0
 15 30  1  0
 20 31  1  0
M  CHG  2  17   1  19  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenylethanone	HMDB
BIA 3-202	HMDB

Chemical Formula

C₁₄H₁₁NO₅

Average Molecular Weight

273.244

Monoisotopic Molecular Weight

273.063722458

IUPAC Name

1-(3,4-dihydroxy-5-nitrophenyl)-2-phenylethan-1-one

Traditional Name

nebicapone

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(=C1O)[N+]([O-])=O)C(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H11NO5/c16-12(6-9-4-2-1-3-5-9)10-7-11(15(19)20)14(18)13(17)8-10/h1-5,7-8,17-18H,6H2

InChI Key

MRFOLGFFTUGAEB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Alkyl-phenylketone
Nitrophenol
Nitrobenzene
Phenylketone
Aryl ketone
Aryl alkyl ketone
Nitroaromatic compound
Benzoyl
Catechol
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
C-nitro compound
Organic nitro compound
Ketone
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Organic oxygen compound
Organic nitrogen compound
Organic salt
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0255496)

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	2.59	ALOGPS
logP	2.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	5.35	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.46 m³·mol⁻¹	ChemAxon
Polarizability	25.99 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	157.901	30932474
DeepCCS	[M-H]-	155.543	30932474
DeepCCS	[M-2H]-	189.558	30932474
DeepCCS	[M+Na]+	164.812	30932474
AllCCS	[M+H]+	160.8	32859911
AllCCS	[M+H-H2O]+	157.0	32859911
AllCCS	[M+NH4]+	164.4	32859911
AllCCS	[M+Na]+	165.4	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	158.5	32859911
AllCCS	[M+HCOO]-	157.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	14.3466 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2270.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	416.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	312.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	679.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	694.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1311.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	531.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1447.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	424.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	296.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	95.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nebicapone	OC1=CC(=CC(=C1O)[N+]([O-])=O)C(=O)CC1=CC=CC=C1	3545.5	Standard polar	33892256
Nebicapone	OC1=CC(=CC(=C1O)[N+]([O-])=O)C(=O)CC1=CC=CC=C1	2266.3	Standard non polar	33892256
Nebicapone	OC1=CC(=CC(=C1O)[N+]([O-])=O)C(=O)CC1=CC=CC=C1	2480.7	Semi standard non polar	33892256

Spectra

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

8014109

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9838389

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

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 Nebicapone (HMDB0255496)

MOL for HMDB0255496 (Nebicapone)

3D MOL for HMDB0255496 (Nebicapone)

3D SDF for HMDB0255496 (Nebicapone)

3D-SDF for HMDB0255496 (Nebicapone)

PDB for HMDB0255496 (Nebicapone)

3D PDB for HMDB0255496 (Nebicapone)

SMILES for HMDB0255496 (Nebicapone)

INCHI for HMDB0255496 (Nebicapone)

Structure for HMDB0255496 (Nebicapone)

3D Structure for HMDB0255496 (Nebicapone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized