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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:22:47 UTC

Update Date

2022-03-07 02:56:44 UTC

HMDB ID

HMDB0040794

Secondary Accession Numbers

HMDB40794

Metabolite Identification

Common Name

5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide

Description

5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.g. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0040794
     RDKit          3D
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide
 31 34  0  0  0  0  0  0  0  0999 V2000
    4.4220   -0.3994    0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -0.2864   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -0.5179   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385   -1.7313   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -2.8176   -0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2460   -1.8845   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2805   -2.9780   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -0.8360   -0.3616 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.6369   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540   -1.4704   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510   -0.9787   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5070    0.3391   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147    1.1940    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.6965    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030    1.3122    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    2.5727    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    2.7778    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141    1.7824    0.2134 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.1588    2.0381    0.2494 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3872    0.5407   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    0.3356   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699   -0.1742    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2736    0.3241    0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088   -1.4049    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -3.7347   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622   -2.4978   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0819   -1.6500   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4996    0.7440    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713    2.2213    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    3.3411    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    3.7791    0.6941 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
  4  6  1  0
  6  7  2  0
  6  8  1  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
 21  8  1  0
 14  9  1  0
 21 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
M  CHG  2  18   1  19  -1
M  END


  Mrv0541 05061312082D          

 21 24  0  0  0  0            999 V2000
    2.0183   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    1.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089    1.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -2.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -2.2179    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
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  2  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040794

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(=O)N2C3=CC=CC=C3C3=C2C1=N(=O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H10N2O4/c1-21-14-12-11-9(6-7-16(12)20)8-4-2-3-5-10(8)17(11)15(19)13(14)18/h2-7,18H,1H3

> <INCHI_KEY>
BACBQAVGXGDIMD-UHFFFAOYSA-N

> <FORMULA>
C15H10N2O4

> <MOLECULAR_WEIGHT>
282.2509

> <EXACT_MASS>
282.064056818

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.682189438454664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4-methoxy-1,6λ⁵-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaene-2,6-dione

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
-0.1309041676666663

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.108863607301378

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0467919884610484

> <JCHEM_POLAR_SURFACE_AREA>
76.92

> <JCHEM_REFRACTIVITY>
77.09019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-methoxy-1,6λ⁵-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040794
     RDKit          3D
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide
 31 34  0  0  0  0  0  0  0  0999 V2000
    4.4220   -0.3994    0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -0.2864   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -0.5179   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385   -1.7313   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -2.8176   -0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2460   -1.8845   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2805   -2.9780   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -0.8360   -0.3616 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.6369   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540   -1.4704   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510   -0.9787   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5070    0.3391   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147    1.1940    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.6965    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030    1.3122    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    2.5727    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    2.7778    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141    1.7824    0.2134 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.1588    2.0381    0.2494 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3872    0.5407   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    0.3356   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699   -0.1742    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2736    0.3241    0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088   -1.4049    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -3.7347   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622   -2.4978   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0819   -1.6500   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4996    0.7440    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713    2.2213    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    3.3411    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    3.7791    0.6941 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
  4  6  1  0
  6  7  2  0
  6  8  1  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
 21  8  1  0
 14  9  1  0
 21 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
M  CHG  2  18   1  19  -1
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       3.767  -4.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.320   4.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.860   4.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.450   3.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.630   3.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.860   2.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.240  -2.600   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       2.430   0.480   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       5.094  -2.599   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.240  -4.140   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.432  -4.140   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    7    9                                                       
CONECT    7    6   16                                                       
CONECT    8    4    9   10                                                  
CONECT    9    6    8   11                                                  
CONECT   10    5    8   17                                                  
CONECT   11    9   12   17                                                  
CONECT   12   11   14   16                                                  
CONECT   13   14   15   18                                                  
CONECT   14   12   13   21                                                  
CONECT   15   13   17   19                                                  
CONECT   16    7   12   20                                                  
CONECT   17   10   11   15                                                  
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    1   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0040794
HETATM    1  C1  UNL     1       4.422  -0.399   0.792  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.579  -0.286  -0.307  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.233  -0.518  -0.337  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.639  -1.731  -0.612  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.452  -2.818  -0.883  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.246  -1.884  -0.623  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.281  -2.978  -0.872  1.00  0.00           O  
HETATM    8  N1  UNL     1      -0.549  -0.836  -0.362  1.00  0.00           N  
HETATM    9  C5  UNL     1      -1.884  -0.637  -0.290  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.954  -1.470  -0.468  1.00  0.00           C  
HETATM   11  C7  UNL     1      -4.251  -0.979  -0.328  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.507   0.339  -0.013  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.415   1.194   0.169  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.136   0.696   0.029  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.903   1.312   0.152  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.443   2.573   0.441  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.923   2.778   0.464  1.00  0.00           C  
HETATM   18  N2  UNL     1       1.814   1.782   0.213  1.00  0.00           N1+
HETATM   19  O4  UNL     1       3.159   2.038   0.249  1.00  0.00           O1-
HETATM   20  C14 UNL     1       1.387   0.541  -0.072  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.020   0.336  -0.095  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.970  -0.174   1.763  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.274   0.324   0.640  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.909  -1.405   0.785  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.094  -3.735  -1.093  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.762  -2.498  -0.714  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.082  -1.650  -0.472  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.500   0.744   0.101  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.571   2.221   0.414  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.167   3.341   0.635  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.284   3.779   0.694  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5    6
CONECT    5   25
CONECT    6    7    7    8
CONECT    8    9   21
CONECT    9   10   10   14
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15
CONECT   15   16   21   21
CONECT   16   17   17   30
CONECT   17   18   31
CONECT   18   19   20   20
CONECT   20   21
END

HMDB0040794
     RDKit          3D
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide
 31 34  0  0  0  0  0  0  0  0999 V2000
    4.4220   -0.3994    0.7919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -0.2864   -0.3066 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -0.5179   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385   -1.7313   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -2.8176   -0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2460   -1.8845   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2805   -2.9780   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493   -0.8360   -0.3616 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.6369   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540   -1.4704   -0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2510   -0.9787   -0.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5070    0.3391   -0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147    1.1940    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.6965    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030    1.3122    0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430    2.5727    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    2.7778    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8141    1.7824    0.2134 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.1588    2.0381    0.2494 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.3872    0.5407   -0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    0.3356   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699   -0.1742    1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2736    0.3241    0.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088   -1.4049    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -3.7347   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622   -2.4978   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0819   -1.6500   -0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4996    0.7440    0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713    2.2213    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    3.3411    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2842    3.7791    0.6941 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
  4  6  1  0
  6  7  2  0
  6  8  1  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  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
 21  8  1  0
 14  9  1  0
 21 15  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
 17 31  1  0
M  CHG  2  18   1  19  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀N₂O₄

Average Molecular Weight

282.2509

Monoisotopic Molecular Weight

282.064056818

IUPAC Name

3-hydroxy-4-methoxy-1,6λ⁵-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaene-2,6-dione

Traditional Name

3-hydroxy-4-methoxy-1,6λ⁵-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaene-2,6-dione

CAS Registry Number

129722-98-1

SMILES

COC1=C(O)C(=O)N2C3=CC=CC=C3C3=C2C1=N(=O)C=C3

InChI Identifier

InChI=1S/C15H10N2O4/c1-21-14-12-11-9(6-7-16(12)20)8-4-2-3-5-10(8)17(11)15(19)13(14)18/h2-7,18H,1H3

InChI Key

BACBQAVGXGDIMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040794)
Cytoplasm (HMDB: HMDB0040794)

Source

Exogenous

Food

Food (HMDB: HMDB0040794)

Not Available

Nutrient (HMDB: HMDB0040794)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °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	0.17 g/L	ALOGPS
logP	0.9	ALOGPS
logP	-0.13	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	5.11	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.09 m³·mol⁻¹	ChemAxon
Polarizability	27.68 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]+	162.718	31661259
DarkChem	[M-H]-	164.619	31661259
DeepCCS	[M+H]+	170.787	30932474
DeepCCS	[M-H]-	168.407	30932474
DeepCCS	[M-2H]-	202.721	30932474
DeepCCS	[M+Na]+	178.395	30932474
AllCCS	[M+H]+	161.4	32859911
AllCCS	[M+H-H2O]+	157.5	32859911
AllCCS	[M+NH4]+	164.9	32859911
AllCCS	[M+Na]+	166.0	32859911
AllCCS	[M-H]-	165.4	32859911
AllCCS	[M+Na-2H]-	164.4	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide	COC1=C(O)C(=O)N2C3=CC=CC=C3C3=C2C1=N(=O)C=C3	3922.4	Standard polar	33892256
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide	COC1=C(O)C(=O)N2C3=CC=CC=C3C3=C2C1=N(=O)C=C3	2706.6	Standard non polar	33892256
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide	COC1=C(O)C(=O)N2C3=CC=CC=C3C3=C2C1=N(=O)C=C3	3057.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(=O)N2C3=CC=CC=C3C3=C2C1=[N+]([O-])C=C3	3000.7	Semi standard non polar	33892256
5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(=O)N2C3=CC=CC=C3C3=C2C1=[N+]([O-])C=C3	3208.9	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 - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-0090000000-de7d1c0ee8e1368721f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-6049000000-e051f1259c6a2db37140	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 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 - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 10V, Positive-QTOF	splash10-001i-0090000000-4a7ac2d88826776c3588	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 20V, Positive-QTOF	splash10-001i-0090000000-2363344fdf4dd678777c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 40V, Positive-QTOF	splash10-0f6x-1690000000-4fd20aef6645375ff536	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 10V, Negative-QTOF	splash10-001i-0090000000-2692531a78352c7a12cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 20V, Negative-QTOF	splash10-001i-0090000000-05b9f9e29ae58245658d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 40V, Negative-QTOF	splash10-0ul0-0290000000-84e46411547810f86662	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 10V, Negative-QTOF	splash10-001i-0090000000-474ffadd74c35f44454a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 20V, Negative-QTOF	splash10-001i-0090000000-474ffadd74c35f44454a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 40V, Negative-QTOF	splash10-0udi-0090000000-5abfb8b0887ef0278e97	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 10V, Positive-QTOF	splash10-001i-0090000000-27c040747a6736174a46	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 20V, Positive-QTOF	splash10-001i-0090000000-27c040747a6736174a46	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide 40V, Positive-QTOF	splash10-0gz0-0490000000-c92f6073d8a1c9004fa7	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020610

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide (HMDB0040794)

MOL for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

3D MOL for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

3D SDF for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

3D-SDF for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

PDB for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

3D PDB for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

SMILES for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

INCHI for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

Structure for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

3D Structure for HMDB0040794 (5-Hydroxy-4-methoxy-6-canthinone 3-N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra