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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:31 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030391

Secondary Accession Numbers

HMDB30391

Metabolite Identification

Common Name

Cepharadione B

Description

Cepharadione B belongs to the class of organic compounds known as 4,5-dioxoaporphines. These are alkaloids that contains the tetracyclic aporphine skeleton with two C=O groups at the 4- and 5-positions. Cepharadione B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cepharadione b has been detected, but not quantified in, herbs and spices. This could make cepharadione b a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030391
     RDKit          3D
Cepharadione B
 39 42  0  0  0  0  0  0  0  0999 V2000
    4.3087    2.0300    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    0.8159    0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2491    0.7602    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    1.9484    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    1.9497    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    0.7554    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780    0.7737   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -0.3828   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.5670   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696   -2.7557   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678   -3.9689   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339   -4.0296    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174   -2.8432    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -1.6301    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -0.4581    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -0.4646    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -1.5614    0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1365   -1.9554   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318    1.9778   -0.4609 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    1.9303   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    3.2193   -0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    4.3095   -0.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4447    3.2405   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    4.3172    0.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.8254    1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    2.7834    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    2.4698   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978    2.8977    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663   -0.4208   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -2.7246   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5602   -4.8859   -0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1013   -4.9484    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1237   -2.9515    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4288   -3.0073   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9976   -1.2701   -0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545   -1.9439   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    2.9345   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970    1.2997    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1058    1.5306   -1.7738 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 16  3  1  0
 23  5  1  0
 15  6  1  0
 14  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
M  END


  Mrv0541 05061305122D          

 24 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
    2.1434   -2.8875    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
    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
    2.8579    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
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 12  1  0  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  2  0  0  0  0
 22 19  2  0  0  0  0
 23  2  1  0  0  0  0
 23 14  1  0  0  0  0
 24  3  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030391

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C3C(=CC4=CC=CC=C24)N(C)C(=O)C(=O)C3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H15NO4/c1-20-13-8-10-6-4-5-7-11(10)16-15(13)12(17(21)19(20)22)9-14(23-2)18(16)24-3/h4-9H,1-3H3

> <INCHI_KEY>
AFKGBLKLNRDQFN-UHFFFAOYSA-N

> <FORMULA>
C19H15NO4

> <MOLECULAR_WEIGHT>
321.3267

> <EXACT_MASS>
321.100107973

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.43591258498578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.4792206119999998

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.399452893423244

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
89.41769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030391
     RDKit          3D
Cepharadione B
 39 42  0  0  0  0  0  0  0  0999 V2000
    4.3087    2.0300    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    0.8159    0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2491    0.7602    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    1.9484    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    1.9497    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    0.7554    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780    0.7737   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -0.3828   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.5670   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696   -2.7557   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678   -3.9689   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339   -4.0296    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174   -2.8432    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -1.6301    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -0.4581    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -0.4646    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -1.5614    0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1365   -1.9554   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318    1.9778   -0.4609 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    1.9303   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    3.2193   -0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    4.3095   -0.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4447    3.2405   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    4.3172    0.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.8254    1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    2.7834    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    2.4698   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978    2.8977    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663   -0.4208   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -2.7246   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5602   -4.8859   -0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1013   -4.9484    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1237   -2.9515    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4288   -3.0073   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9976   -1.2701   -0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545   -1.9439   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    2.9345   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970    1.2997    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1058    1.5306   -1.7738 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 16  3  1  0
 23  5  1  0
 15  6  1  0
 14  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   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  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8   10   13                                                       
CONECT    9   12   14                                                       
CONECT   10    6    8   11                                                  
CONECT   11    7   10   16                                                  
CONECT   12    9   15   17                                                  
CONECT   13    8   15   20                                                  
CONECT   14    9   18   23                                                  
CONECT   15   12   13   16                                                  
CONECT   16   11   15   18                                                  
CONECT   17   12   19   21                                                  
CONECT   18   14   16   24                                                  
CONECT   19   17   20   22                                                  
CONECT   20    1   13   19                                                  
CONECT   21   17                                                            
CONECT   22   19                                                            
CONECT   23    2   14                                                       
CONECT   24    3   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0030391
HETATM    1  C1  UNL     1       4.309   2.030   0.956  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.621   0.816   0.860  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.249   0.760   0.577  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.593   1.948   0.395  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.235   1.950   0.114  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.428   0.755   0.025  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.778   0.774  -0.255  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.516  -0.383  -0.356  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.848  -1.567  -0.162  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.570  -2.756  -0.220  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.968  -3.969  -0.000  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.634  -4.030   0.283  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.117  -2.843   0.347  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.473  -1.630   0.125  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.254  -0.458   0.216  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.589  -0.465   0.487  1.00  0.00           C  
HETATM   17  O2  UNL     1       2.387  -1.561   0.683  1.00  0.00           O  
HETATM   18  C16 UNL     1       3.136  -1.955  -0.523  1.00  0.00           C  
HETATM   19  N1  UNL     1      -2.532   1.978  -0.461  1.00  0.00           N  
HETATM   20  C17 UNL     1      -3.958   1.930  -0.754  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.851   3.219  -0.371  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.463   4.309  -0.543  1.00  0.00           O  
HETATM   23  C19 UNL     1      -0.445   3.241  -0.080  1.00  0.00           C  
HETATM   24  O4  UNL     1       0.202   4.317   0.009  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.297   1.825   1.429  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.805   2.783   1.594  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.414   2.470  -0.060  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.098   2.898   0.464  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.566  -0.421  -0.574  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.631  -2.725  -0.443  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.560  -4.886  -0.054  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.101  -4.948   0.467  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.124  -2.952   0.618  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.429  -3.007  -0.345  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.998  -1.270  -0.650  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.454  -1.944  -1.392  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.386   2.935  -0.692  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.497   1.300   0.003  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.106   1.531  -1.774  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   28
CONECT    5    6    6   23
CONECT    6    7   15
CONECT    7    8    8   19
CONECT    8    9   29
CONECT    9   10   10   14
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15
CONECT   15   16   16
CONECT   16   17
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   20   21
CONECT   20   37   38   39
CONECT   21   22   22   23
CONECT   23   24   24
END

HMDB0030391
     RDKit          3D
Cepharadione B
 39 42  0  0  0  0  0  0  0  0999 V2000
    4.3087    2.0300    0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6209    0.8159    0.8600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2491    0.7602    0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    1.9484    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348    1.9497    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    0.7554    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7780    0.7737   -0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -0.3828   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.5670   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5696   -2.7557   -0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9678   -3.9689   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6339   -4.0296    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1174   -2.8432    0.3469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -1.6301    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -0.4581    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5887   -0.4646    0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -1.5614    0.6826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1365   -1.9554   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318    1.9778   -0.4609 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    1.9303   -0.7543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    3.2193   -0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    4.3095   -0.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4447    3.2405   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2018    4.3172    0.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2967    1.8254    1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049    2.7834    1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4143    2.4698   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978    2.8977    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663   -0.4208   -0.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -2.7246   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5602   -4.8859   -0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1013   -4.9484    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1237   -2.9515    0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4288   -3.0073   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9976   -1.2701   -0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545   -1.9439   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3855    2.9345   -0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970    1.2997    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1058    1.5306   -1.7738 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 16  3  1  0
 23  5  1  0
 15  6  1  0
 14  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  8 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dimethoxy-6-methyl-4H-dibenzo[de,g]quinoline-4,5(6H)-dione, 9ci	HMDB
Cepharadione b	MeSH

Chemical Formula

C₁₉H₁₅NO₄

Average Molecular Weight

321.3267

Monoisotopic Molecular Weight

321.100107973

IUPAC Name

15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

Traditional Name

15,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

CAS Registry Number

55610-02-1

SMILES

COC1=C(OC)C2=C3C(=CC4=CC=CC=C24)N(C)C(=O)C(=O)C3=C1

InChI Identifier

InChI=1S/C19H15NO4/c1-20-13-8-10-6-4-5-7-11(10)16-15(13)12(17(21)19(20)22)9-14(23-2)18(16)24-3/h4-9H,1-3H3

InChI Key

AFKGBLKLNRDQFN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4,5-dioxoaporphines. These are alkaloids that contains the tetracyclic aporphine skeleton with two C=O groups at the 4- and 5-positions.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

4,5-dioxoaporphines

Direct Parent

4,5-dioxoaporphines

Alternative Parents

Substituents

4,5-dioxoaporphine
Benzoquinoline
Phenanthrene
Isoquinolone
Quinolone
Quinoline
Naphthalene
Anisole
Aryl ketone
Alkyl aryl ether
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ketone
Lactam
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030391)

Cellular substructure

Membrane (HMDB: HMDB0030391)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030391)

Source

Endogenous

Endogenous (HMDB: HMDB0030391)

Plant

Plant (HMDB: HMDB0030391)

Exogenous

Food

Food (HMDB: HMDB0030391)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	267 - 268 °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	0.005 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.48	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.4	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	2	ChemAxon
Refractivity	89.42 m³·mol⁻¹	ChemAxon
Polarizability	33.44 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.125	31661259
DarkChem	[M-H]-	176.508	31661259
DeepCCS	[M-2H]-	212.12	30932474
DeepCCS	[M+Na]+	187.348	30932474
AllCCS	[M+H]+	173.4	32859911
AllCCS	[M+H-H2O]+	170.0	32859911
AllCCS	[M+NH4]+	176.6	32859911
AllCCS	[M+Na]+	177.5	32859911
AllCCS	[M-H]-	180.3	32859911
AllCCS	[M+Na-2H]-	179.6	32859911
AllCCS	[M+HCOO]-	178.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cepharadione B	COC1=C(OC)C2=C3C(=CC4=CC=CC=C24)N(C)C(=O)C(=O)C3=C1	4524.1	Standard polar	33892256
Cepharadione B	COC1=C(OC)C2=C3C(=CC4=CC=CC=C24)N(C)C(=O)C(=O)C3=C1	2762.0	Standard non polar	33892256
Cepharadione B	COC1=C(OC)C2=C3C(=CC4=CC=CC=C24)N(C)C(=O)C(=O)C3=C1	3210.5	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 B GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0092000000-b2d5895478ac87fe9754	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cepharadione B 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 B 10V, Positive-QTOF	splash10-00di-0009000000-8c960a6eee954541d5c1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 20V, Positive-QTOF	splash10-00di-0039000000-cc1c2ed9c2443ae59699	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 40V, Positive-QTOF	splash10-052r-0091000000-9bf5c59f6d2c2ef31ed2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 10V, Negative-QTOF	splash10-00di-0009000000-357ba6e8c52fd4ed7d60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 20V, Negative-QTOF	splash10-00di-1029000000-d37d9356c14f3ebf2912	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 40V, Negative-QTOF	splash10-0kos-2092000000-69b397d19137d14c4dc7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 10V, Positive-QTOF	splash10-00di-0009000000-f52046137381c8e84ef0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 20V, Positive-QTOF	splash10-00di-0019000000-cc88f77bf31f888f51c5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 40V, Positive-QTOF	splash10-000l-0091000000-94d3004136a8f90c8dca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 10V, Negative-QTOF	splash10-00di-0009000000-293bbbfd7c5c9080178e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 20V, Negative-QTOF	splash10-00di-0009000000-293bbbfd7c5c9080178e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cepharadione B 40V, Negative-QTOF	splash10-03dl-0091000000-066c77341b0b8463fd07	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

FDB002244

KNApSAcK ID

C00025788

Chemspider ID

164349

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

189151

PDB ID

Not Available

ChEBI ID

503150

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 B (HMDB0030391)

MOL for HMDB0030391 (Cepharadione B)

3D MOL for HMDB0030391 (Cepharadione B)

3D SDF for HMDB0030391 (Cepharadione B)

3D-SDF for HMDB0030391 (Cepharadione B)

PDB for HMDB0030391 (Cepharadione B)

3D PDB for HMDB0030391 (Cepharadione B)

SMILES for HMDB0030391 (Cepharadione B)

INCHI for HMDB0030391 (Cepharadione B)

Structure for HMDB0030391 (Cepharadione B)

3D Structure for HMDB0030391 (Cepharadione B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra