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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:33 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030227

Secondary Accession Numbers

HMDB30227

Metabolite Identification

Common Name

5-Methoxycanthin-6-one

Description

5-Methoxycanthin-6-one 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-Methoxycanthin-6-one is a strong basic compound (based on its pKa). Alkaloid from the wood of Picrasma excelsa (Jamaican quassiawood).

Structure

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

HMDB0030227
     RDKit          3D
5-Methoxycanthin-6-one
 29 32  0  0  0  0  0  0  0  0999 V2000
    4.7337   -0.8048    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839   -1.4194    0.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293   -0.6377    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.7377    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287    1.4216   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1241    2.7704   -0.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    3.3514   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    2.6374   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.2513   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.2084   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571    0.1409   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -1.0787   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3894   -2.2588   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164   -2.1832   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3549   -0.9795   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0541   -0.6145   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989   -1.3021   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -2.5575   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508    0.7167   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389   -0.2669   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722   -0.0074    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5460   -1.4682    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397    1.2669    0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373    4.4254   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    3.0782   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0132    1.0656   -0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895   -1.1735   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119   -3.2271   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371   -3.0924   -0.2590 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 16 19  1  0
 17  3  1  0
 19  5  1  0
 19  9  2  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
M  END


  Mrv0541 05061305052D          

 19 22  0  0  0  0            999 V2000
    2.7295   -2.2174    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
    1.3018   -1.3929    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
    0.5839   -0.9804    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
    2.0143   -0.9804    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
    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    0.2567    0.0000 O   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
  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
  9  4  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  2  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 15  2  0  0  0  0
 19  1  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030227

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10N2O2/c1-19-13-8-11-14-10(6-7-16-11)9-4-2-3-5-12(9)17(14)15(13)18/h2-8H,1H3

> <INCHI_KEY>
TXEFUSAHPIYZHD-UHFFFAOYSA-N

> <FORMULA>
C15H10N2O2

> <MOLECULAR_WEIGHT>
250.2521

> <EXACT_MASS>
250.074227574

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.86969406655657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
1.6788726793333333

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.1505653938502283

> <JCHEM_POLAR_SURFACE_AREA>
44.120000000000005

> <JCHEM_REFRACTIVITY>
71.2153

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030227
     RDKit          3D
5-Methoxycanthin-6-one
 29 32  0  0  0  0  0  0  0  0999 V2000
    4.7337   -0.8048    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839   -1.4194    0.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293   -0.6377    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.7377    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287    1.4216   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1241    2.7704   -0.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    3.3514   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    2.6374   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.2513   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.2084   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571    0.1409   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -1.0787   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3894   -2.2588   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164   -2.1832   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3549   -0.9795   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0541   -0.6145   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989   -1.3021   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -2.5575   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508    0.7167   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389   -0.2669   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722   -0.0074    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5460   -1.4682    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397    1.2669    0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373    4.4254   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    3.0782   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0132    1.0656   -0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895   -1.1735   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119   -3.2271   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371   -3.0924   -0.2590 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 16 19  1  0
 17  3  1  0
 19  5  1  0
 19  9  2  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  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       5.095  -4.139   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       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.860   2.080   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       1.090  -0.290   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   0.479   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.094  -2.599   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   12                                                       
CONECT    6    7   10                                                       
CONECT    7    6   16                                                       
CONECT    8   11   13                                                       
CONECT    9    4   10   12                                                  
CONECT   10    6    9   14                                                  
CONECT   11    8   14   16                                                  
CONECT   12    5    9   17                                                  
CONECT   13    8   15   19                                                  
CONECT   14   10   11   17                                                  
CONECT   15   13   17   18                                                  
CONECT   16    7   11                                                       
CONECT   17   12   14   15                                                  
CONECT   18   15                                                            
CONECT   19    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0030227
HETATM    1  C1  UNL     1       4.734  -0.805   0.160  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.484  -1.419   0.075  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.329  -0.638   0.001  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.427   0.738   0.013  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.229   1.422  -0.064  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.124   2.770  -0.065  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.098   3.351  -0.144  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.278   2.637  -0.225  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.194   1.251  -0.225  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.088   0.208  -0.289  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.457   0.141  -0.380  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.117  -1.079  -0.429  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.389  -2.259  -0.385  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.016  -2.183  -0.294  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.355  -0.980  -0.245  1.00  0.00           C  
HETATM   16  N2  UNL     1      -0.054  -0.615  -0.157  1.00  0.00           N  
HETATM   17  C14 UNL     1       1.099  -1.302  -0.083  1.00  0.00           C  
HETATM   18  O2  UNL     1       1.021  -2.557  -0.093  1.00  0.00           O  
HETATM   19  C15 UNL     1       0.051   0.717  -0.145  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.939  -0.267  -0.793  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.672  -0.007   0.948  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.546  -1.468   0.459  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.340   1.267   0.076  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.137   4.425  -0.142  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.259   3.078  -0.289  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.013   1.066  -0.413  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.189  -1.173  -0.501  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.912  -3.227  -0.424  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.437  -3.092  -0.259  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   23
CONECT    5    6    6   19
CONECT    6    7
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   19   19
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   19
CONECT   17   18   18
END

HMDB0030227
     RDKit          3D
5-Methoxycanthin-6-one
 29 32  0  0  0  0  0  0  0  0999 V2000
    4.7337   -0.8048    0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839   -1.4194    0.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293   -0.6377    0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.7377    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287    1.4216   -0.0635 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1241    2.7704   -0.0650 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    3.3514   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    2.6374   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1942    1.2513   -0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.2084   -0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4571    0.1409   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174   -1.0787   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3894   -2.2588   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164   -2.1832   -0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3549   -0.9795   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0541   -0.6145   -0.1571 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989   -1.3021   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -2.5575   -0.0935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508    0.7167   -0.1447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389   -0.2669   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722   -0.0074    0.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5460   -1.4682    0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3397    1.2669    0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1373    4.4254   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    3.0782   -0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0132    1.0656   -0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1895   -1.1735   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119   -3.2271   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371   -3.0924   -0.2590 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  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 16 19  1  0
 17  3  1  0
 19  5  1  0
 19  9  2  0
 15 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Methoxy-6H-indolo(3,2,1-de)(1,5)naphthyridin-6-one	HMDB
5-Methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one	HMDB
5-Methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one, 9ci	HMDB
5-Methoxy-canthin-6-one	HMDB
5-Methoxycanthin-6-one	MeSH

Chemical Formula

C₁₅H₁₀N₂O₂

Average Molecular Weight

250.2521

Monoisotopic Molecular Weight

250.074227574

IUPAC Name

3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one

Traditional Name

3-methoxy-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5,7,9(16),10,12,14-heptaen-2-one

CAS Registry Number

15071-56-4

SMILES

COC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O

InChI Identifier

InChI=1S/C15H10N2O2/c1-19-13-8-11-14-10(6-7-16-11)9-4-2-3-5-12(9)17(14)15(13)18/h2-8H,1H3

InChI Key

TXEFUSAHPIYZHD-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

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Pyridinone
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Lactam
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030227)

Cellular substructure

Membrane (HMDB: HMDB0030227)

Source

Endogenous

Endogenous (HMDB: HMDB0030227)

Exogenous

Food

Food (HMDB: HMDB0030227)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	243 - 244 °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	0.11 g/L	ALOGPS
logP	2.72	ALOGPS
logP	1.68	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	3.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.12 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.22 m³·mol⁻¹	ChemAxon
Polarizability	25.87 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]+	157.257	31661259
DarkChem	[M-H]-	156.503	31661259
DeepCCS	[M-2H]-	190.235	30932474
DeepCCS	[M+Na]+	165.8	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	160.4	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	158.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxycanthin-6-one	COC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O	3366.6	Standard polar	33892256
5-Methoxycanthin-6-one	COC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O	2459.1	Standard non polar	33892256
5-Methoxycanthin-6-one	COC1=CC2=NC=CC3=C2N(C2=CC=CC=C32)C1=O	2535.7	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-Methoxycanthin-6-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0490000000-f1860259b35079360f07	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methoxycanthin-6-one 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-Methoxycanthin-6-one 10V, Positive-QTOF	splash10-0udi-0090000000-087c85fcbf011bb838ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Positive-QTOF	splash10-0udi-0090000000-51012159796bca1ea8d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Positive-QTOF	splash10-00di-0390000000-8d27d5f34a9d9340e800	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 10V, Negative-QTOF	splash10-0002-0090000000-53e7b115923dfd043f33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Negative-QTOF	splash10-0002-0090000000-2d114b98cc00ff75b9b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Negative-QTOF	splash10-014i-0390000000-2ddc80db905851cc2b6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 10V, Positive-QTOF	splash10-0udi-0090000000-01844139d9a1e29fbe91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Positive-QTOF	splash10-0udi-0090000000-01844139d9a1e29fbe91	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Positive-QTOF	splash10-0umi-0890000000-806cddf1b93a105cce4f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 10V, Negative-QTOF	splash10-0002-0090000000-6971a302c8bdd54e5834	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 20V, Negative-QTOF	splash10-0002-0090000000-6971a302c8bdd54e5834	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methoxycanthin-6-one 40V, Negative-QTOF	splash10-016r-0590000000-2c58456b19a8c665fb26	2021-09-24	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

FDB002046

KNApSAcK ID

Not Available

Chemspider ID

227523

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

259218

PDB ID

Not Available

ChEBI ID

544162

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-Methoxycanthin-6-one (HMDB0030227)

MOL for HMDB0030227 (5-Methoxycanthin-6-one)

3D MOL for HMDB0030227 (5-Methoxycanthin-6-one)

3D SDF for HMDB0030227 (5-Methoxycanthin-6-one)

3D-SDF for HMDB0030227 (5-Methoxycanthin-6-one)

PDB for HMDB0030227 (5-Methoxycanthin-6-one)

3D PDB for HMDB0030227 (5-Methoxycanthin-6-one)

SMILES for HMDB0030227 (5-Methoxycanthin-6-one)

INCHI for HMDB0030227 (5-Methoxycanthin-6-one)

Structure for HMDB0030227 (5-Methoxycanthin-6-one)

3D Structure for HMDB0030227 (5-Methoxycanthin-6-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra