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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:11:20 UTC

Update Date

2022-03-07 02:54:04 UTC

HMDB ID

HMDB0034364

Secondary Accession Numbers

HMDB34364

Metabolite Identification

Common Name

Cepharadione A

Description

Cepharadione A belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Cepharadione A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cepharadione a has been detected, but not quantified in, herbs and spices. This could make cepharadione a a potential biomarker for the consumption of these foods.

Structure

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

HMDB0034364
     RDKit          3D
Cepharadione A
 34 38  0  0  0  0  0  0  0  0999 V2000
   -3.9580   -1.0023    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    0.0418    0.1206 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    1.4148    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802    1.6561    0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    2.4389    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355    3.6373    0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    2.0418    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0896    2.9764    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    2.6218   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2851   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7862    0.3452   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.7009    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664   -0.2421    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245   -1.5762   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -1.9629   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119   -3.3206   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216   -3.7182   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -2.8048   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961   -1.4339   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949   -0.9960   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614    1.3192   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    2.5554    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    3.4184   -0.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7120   -1.7996    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947   -1.4486   -0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167   -0.5603    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    4.0169    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763   -2.3736   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -4.0418   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -4.7760   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784   -3.0737   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909   -0.7160   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5505    2.8475   -0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    2.5290    1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 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
 10 21  1  0
 21 22  1  0
 22 23  1  0
 13  2  1  0
 20 15  1  0
 12  7  1  0
 23  9  1  0
 20 11  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 22 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061307452D          

 23 27  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    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
    2.1434    1.2375    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
    2.4209   -2.5432    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
    2.8579    0.0000    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
    1.4289    0.8250    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
    1.4289    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
    0.0000    0.0000    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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -2.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565   -1.7895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  2  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  1  0  0  0  0
 20 16  2  0  0  0  0
 21 18  2  0  0  0  0
 22  8  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034364

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H11NO4/c1-19-12-6-9-4-2-3-5-10(9)15-14(12)11(16(20)18(19)21)7-13-17(15)23-8-22-13/h2-7H,8H2,1H3

> <INCHI_KEY>
RZIGKFTVXWUUCX-UHFFFAOYSA-N

> <FORMULA>
C18H11NO4

> <MOLECULAR_WEIGHT>
305.2842

> <EXACT_MASS>
305.068807845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.988978809794904

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.417796611

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.483000080717728

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
82.25819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034364
     RDKit          3D
Cepharadione A
 34 38  0  0  0  0  0  0  0  0999 V2000
   -3.9580   -1.0023    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    0.0418    0.1206 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    1.4148    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802    1.6561    0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    2.4389    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355    3.6373    0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    2.0418    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0896    2.9764    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    2.6218   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2851   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7862    0.3452   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.7009    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664   -0.2421    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245   -1.5762   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -1.9629   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119   -3.3206   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216   -3.7182   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -2.8048   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961   -1.4339   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949   -0.9960   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614    1.3192   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    2.5554    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    3.4184   -0.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7120   -1.7996    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947   -1.4486   -0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167   -0.5603    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    4.0169    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763   -2.3736   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -4.0418   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -4.7760   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784   -3.0737   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909   -0.7160   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5505    2.8475   -0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    2.5290    1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 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
 10 21  1  0
 21 22  1  0
 22 23  1  0
 13  2  1  0
 20 15  1  0
 12  7  1  0
 23  9  1  0
 20 11  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 22 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.519  -4.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   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       2.667   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.988  -4.586   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.145  -3.340   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    9   12                                                       
CONECT    7   11   13                                                       
CONECT    8   22   23                                                       
CONECT    9    4    6   10                                                  
CONECT   10    5    9   15                                                  
CONECT   11    7   14   16                                                  
CONECT   12    6   14   19                                                  
CONECT   13    7   17   22                                                  
CONECT   14   11   12   15                                                  
CONECT   15   10   14   17                                                  
CONECT   16   11   18   20                                                  
CONECT   17   13   15   23                                                  
CONECT   18   16   19   21                                                  
CONECT   19    1   12   18                                                  
CONECT   20   16                                                            
CONECT   21   18                                                            
CONECT   22    8   13                                                       
CONECT   23    8   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0034364
HETATM    1  C1  UNL     1      -3.958  -1.002   0.139  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.951   0.042   0.121  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.349   1.415   0.193  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.580   1.656   0.271  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.329   2.439   0.173  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.636   3.637   0.233  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.936   2.042   0.080  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.090   2.976   0.056  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.413   2.622  -0.032  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.786   1.285  -0.101  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.786   0.345  -0.079  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.560   0.701   0.010  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.566  -0.242   0.032  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.224  -1.576  -0.035  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.098  -1.963  -0.124  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.412  -3.321  -0.190  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.722  -3.718  -0.278  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.728  -2.805  -0.301  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.396  -1.434  -0.234  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.095  -0.996  -0.145  1.00  0.00           C  
HETATM   21  O3  UNL     1       3.161   1.319  -0.178  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.686   2.555   0.188  1.00  0.00           C  
HETATM   23  O4  UNL     1       2.572   3.418  -0.068  1.00  0.00           O  
HETATM   24  H1  UNL     1      -3.712  -1.800   0.886  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.095  -1.449  -0.886  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.917  -0.560   0.489  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.223   4.017   0.111  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.976  -2.374  -0.022  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.382  -4.042  -0.172  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.984  -4.776  -0.331  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.778  -3.074  -0.370  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.191  -0.716  -0.252  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.550   2.848  -0.450  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.946   2.529   1.265  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   13
CONECT    3    4    4    5
CONECT    5    6    6    7
CONECT    7    8    8   12
CONECT    8    9   27
CONECT    9   10   10   23
CONECT   10   11   21
CONECT   11   12   20   20
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   15   28
CONECT   15   16   20
CONECT   16   17   17   29
CONECT   17   18   30
CONECT   18   19   19   31
CONECT   19   20   32
CONECT   21   22
CONECT   22   23   33   34
END

HMDB0034364
     RDKit          3D
Cepharadione A
 34 38  0  0  0  0  0  0  0  0999 V2000
   -3.9580   -1.0023    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    0.0418    0.1206 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3492    1.4148    0.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802    1.6561    0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    2.4389    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355    3.6373    0.2335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9362    2.0418    0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0896    2.9764    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4133    2.6218   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2851   -0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7862    0.3452   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598    0.7009    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664   -0.2421    0.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245   -1.5762   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -1.9629   -0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4119   -3.3206   -0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7216   -3.7182   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284   -2.8048   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961   -1.4339   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949   -0.9960   -0.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1614    1.3192   -0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    2.5554    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    3.4184   -0.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7120   -1.7996    0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947   -1.4486   -0.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9167   -0.5603    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    4.0169    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9763   -2.3736   -0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -4.0418   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9837   -4.7760   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784   -3.0737   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909   -0.7160   -0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5505    2.8475   -0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455    2.5290    1.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 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
 10 21  1  0
 21 22  1  0
 22 23  1  0
 13  2  1  0
 20 15  1  0
 12  7  1  0
 23  9  1  0
 20 11  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  8 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 22 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione, 9ci	HMDB
Cepharadione a	MeSH

Chemical Formula

C₁₈H₁₁NO₄

Average Molecular Weight

305.2842

Monoisotopic Molecular Weight

305.068807845

IUPAC Name

11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione

Traditional Name

11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,12,14,16,18-heptaene-9,10-dione

CAS Registry Number

55610-01-0

SMILES

CN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31

InChI Identifier

InChI=1S/C18H11NO4/c1-19-12-6-9-4-2-3-5-10(9)15-14(12)11(16(20)18(19)21)7-13-17(15)23-8-22-13/h2-7H,8H2,1H3

InChI Key

RZIGKFTVXWUUCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Dihydroquinolone
Isoquinolone
Dihydroquinoline
Isoquinoline
Naphthalene
Quinoline
Benzodioxole
Pyridinone
Benzenoid
Pyridine
Heteroaromatic compound
Lactam
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034364)

Cellular substructure

Membrane (HMDB: HMDB0034364)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034364)

Source

Exogenous

Food

Food (HMDB: HMDB0034364)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034364)

Not Available

Nutrient (HMDB: HMDB0034364)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	340 - 342 °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	0.038 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.42	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.26 m³·mol⁻¹	ChemAxon
Polarizability	30.99 Å³	ChemAxon
Number of Rings	5	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]+	169.473	31661259
DarkChem	[M-H]-	167.553	31661259
DeepCCS	[M-2H]-	198.046	30932474
DeepCCS	[M+Na]+	173.231	30932474
AllCCS	[M+H]+	168.7	32859911
AllCCS	[M+H-H2O]+	165.2	32859911
AllCCS	[M+NH4]+	172.1	32859911
AllCCS	[M+Na]+	173.0	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	172.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cepharadione A	CN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	4337.6	Standard polar	33892256
Cepharadione A	CN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	2776.2	Standard non polar	33892256
Cepharadione A	CN1C(=O)C(=O)C2=CC3=C(OCO3)C3=C2C1=CC1=CC=CC=C31	3307.3	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 - Cepharadione A GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-0092000000-77a5097731b3c195875e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cepharadione A 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 - Cepharadione A 10V, Positive-QTOF	splash10-0a4i-0009000000-eba3560d3db4d6b503eb	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 20V, Positive-QTOF	splash10-0a4i-0039000000-19c01a15c26b3c1c139f	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 40V, Positive-QTOF	splash10-0w90-1090000000-1402a0296675eaece20b	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 10V, Negative-QTOF	splash10-0udi-0009000000-e2636b9737b16ab74ef6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 20V, Negative-QTOF	splash10-0udi-2039000000-1ee3542a3f3724d8731b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 40V, Negative-QTOF	splash10-0kvk-4090000000-3864de5d2d7f29082075	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 10V, Negative-QTOF	splash10-0udi-0009000000-4d7aa01ab3f7fcfbea79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 20V, Negative-QTOF	splash10-0udi-0009000000-4d7aa01ab3f7fcfbea79	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 40V, Negative-QTOF	splash10-0ufr-1095000000-bee69bfa99d0ba2ad6bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 10V, Positive-QTOF	splash10-0a4i-0009000000-fa89142e4337defa1ebe	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 20V, Positive-QTOF	splash10-0a4i-0019000000-c65c30077384b45f2a18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione A 40V, Positive-QTOF	splash10-0kdi-0093000000-f0d3b800456e6c93e3f4	2021-09-25	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

FDB012737

KNApSAcK ID

C00025787

Chemspider ID

85344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

94577

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 Cepharadione A (HMDB0034364)

MOL for HMDB0034364 (Cepharadione A)

3D MOL for HMDB0034364 (Cepharadione A)

3D SDF for HMDB0034364 (Cepharadione A)

3D-SDF for HMDB0034364 (Cepharadione A)

PDB for HMDB0034364 (Cepharadione A)

3D PDB for HMDB0034364 (Cepharadione A)

SMILES for HMDB0034364 (Cepharadione A)

INCHI for HMDB0034364 (Cepharadione A)

Structure for HMDB0034364 (Cepharadione A)

3D Structure for HMDB0034364 (Cepharadione A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra