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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:23:00 UTC

Update Date

2022-03-07 02:56:44 UTC

HMDB ID

HMDB0040798

Secondary Accession Numbers

HMDB40798

Metabolite Identification

Common Name

5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione

Description

5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione, also known as 5-propenylguaethol or isosafroeugenol, 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. Based on a literature review very few articles have been published on 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione.

Structure

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

HMDB0040798
     RDKit          3D
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione
 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.9241    0.6936    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    0.7779   -0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8503    0.8545   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176    2.0948   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102    3.2229    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468    2.1628    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    3.2729    0.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    1.0448   -0.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317    0.7696    0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260    1.5622    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5784    0.9769    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.3849    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -1.2010   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4076   -0.6127   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -1.1540   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -2.4316   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -2.5654   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2465   -3.7209   -0.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -1.5244   -0.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -1.7338   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1031   -0.2971   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -0.1164   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4146    0.0437    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    1.7144    1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9730    0.3839    0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    4.1149    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    2.6367    0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4552    1.5993    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7547   -0.8437   -0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -2.2669   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919   -3.2511   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -1.0906   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1136   -2.7529   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5654   -1.9787    0.4164 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  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  3  1  0
 22  8  1  0
 14  9  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 20 32  1  0
 20 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061312082D          

 22 25  0  0  0  0            999 V2000
   -0.1286   -2.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.1714    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
   -0.8411   -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
    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
   -1.5558   -1.3924    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
    2.7290    0.2567    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
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  1  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 20 14  1  0  0  0  0
 21 16  2  0  0  0  0
 22  2  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040798

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C16H12N2O4/c1-17-11(19)7-9-8-5-3-4-6-10(8)18-12(9)13(17)15(22-2)14(20)16(18)21/h3-7,20H,1-2H3

> <INCHI_KEY>
CQFOPDQAOBCODL-UHFFFAOYSA-N

> <FORMULA>
C16H12N2O4

> <MOLECULAR_WEIGHT>
296.2775

> <EXACT_MASS>
296.079706882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.76283936849481

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
0.14046551400000018

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.68741236591167

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3169299500452376

> <JCHEM_POLAR_SURFACE_AREA>
70.08

> <JCHEM_REFRACTIVITY>
82.44489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040798
     RDKit          3D
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione
 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.9241    0.6936    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    0.7779   -0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8503    0.8545   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176    2.0948   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102    3.2229    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468    2.1628    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    3.2729    0.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    1.0448   -0.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317    0.7696    0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260    1.5622    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5784    0.9769    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.3849    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -1.2010   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4076   -0.6127   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -1.1540   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -2.4316   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -2.5654   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2465   -3.7209   -0.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -1.5244   -0.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -1.7338   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1031   -0.2971   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -0.1164   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4146    0.0437    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    1.7144    1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9730    0.3839    0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    4.1149    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    2.6367    0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4552    1.5993    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7547   -0.8437   -0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -2.2669   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919   -3.2511   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -1.0906   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1136   -2.7529   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5654   -1.9787    0.4164 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  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  3  1  0
 22  8  1  0
 14  9  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 20 32  1  0
 20 33  1  0
 20 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      -0.240  -4.140   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.767  -4.908   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.320   4.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.860   4.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.450   3.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.630   3.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.570  -0.290   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      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.240  -2.600   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       2.430   0.480   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -2.904  -2.599   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.094  -2.599   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.432  -4.140   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   22                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4   10                                                       
CONECT    7    9   11                                                       
CONECT    8    5    9   10                                                  
CONECT    9    7    8   12                                                  
CONECT   10    6    8   18                                                  
CONECT   11    7   17   19                                                  
CONECT   12    9   13   18                                                  
CONECT   13   12   15   17                                                  
CONECT   14   15   16   20                                                  
CONECT   15   13   14   22                                                  
CONECT   16   14   18   21                                                  
CONECT   17    1   11   13                                                  
CONECT   18   10   12   16                                                  
CONECT   19   11                                                            
CONECT   20   14                                                            
CONECT   21   16                                                            
CONECT   22    2   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0040798
HETATM    1  C1  UNL     1      -3.924   0.694   1.023  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.223   0.778  -0.232  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.850   0.855  -0.163  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.218   2.095  -0.005  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.010   3.223   0.076  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.147   2.163   0.065  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.751   3.273   0.208  1.00  0.00           O  
HETATM    8  N1  UNL     1       0.903   1.045  -0.017  1.00  0.00           N  
HETATM    9  C5  UNL     1       2.232   0.770   0.012  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.326   1.562   0.144  1.00  0.00           C  
HETATM   11  C7  UNL     1       4.578   0.977   0.137  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.758  -0.385   0.000  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.637  -1.201  -0.136  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.408  -0.613  -0.128  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.120  -1.154  -0.242  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.614  -2.432  -0.405  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.750  -2.565  -0.484  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.247  -3.721  -0.633  1.00  0.00           O  
HETATM   19  N2  UNL     1      -1.630  -1.524  -0.410  1.00  0.00           N  
HETATM   20  C14 UNL     1      -3.042  -1.734  -0.524  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.103  -0.297  -0.250  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.267  -0.116  -0.168  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.415   0.044   1.737  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.956   1.714   1.493  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.973   0.384   0.826  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.563   4.115   0.189  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.191   2.637   0.253  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.455   1.599   0.242  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.755  -0.844  -0.005  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.734  -2.267  -0.245  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.292  -3.251  -0.463  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.583  -1.091  -1.234  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.114  -2.753  -1.077  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.565  -1.979   0.416  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5    6
CONECT    5   26
CONECT    6    7    7    8
CONECT    8    9   22
CONECT    9   10   10   14
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15
CONECT   15   16   16   22
CONECT   16   17   31
CONECT   17   18   18   19
CONECT   19   20   21
CONECT   20   32   33   34
CONECT   21   22   22
END

HMDB0040798
     RDKit          3D
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione
 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.9241    0.6936    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2232    0.7779   -0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8503    0.8545   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2176    2.0948   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102    3.2229    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468    2.1628    0.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7507    3.2729    0.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    1.0448   -0.0175 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2317    0.7696    0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3260    1.5622    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5784    0.9769    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580   -0.3849    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -1.2010   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4076   -0.6127   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -1.1540   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137   -2.4316   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -2.5654   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2465   -3.7209   -0.6334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -1.5244   -0.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -1.7338   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1031   -0.2971   -0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -0.1164   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4146    0.0437    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565    1.7144    1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9730    0.3839    0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    4.1149    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907    2.6367    0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4552    1.5993    0.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7547   -0.8437   -0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -2.2669   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2919   -3.2511   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -1.0906   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1136   -2.7529   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5654   -1.9787    0.4164 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  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21  3  1  0
 22  8  1  0
 14  9  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
 20 32  1  0
 20 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Ethoxy-5-(1-propenyl)phenol, 9ci	HMDB
2-Ethoxy-5-[(1E)-1-propenyl]phenol	HMDB
5-Propenylguaethol	HMDB
6-Ethoxy-m-anol	HMDB
FEMA 2922	HMDB
Hydroxy methyl anethol	HMDB
Isosafroeugenol	HMDB
Isosafroeugenole	HMDB
Propenyl guaethol	HMDB
Propenylguaethol	HMDB
Propenylguaethole	HMDB
Propenylguaetol	HMDB
trans-2-Ethoxy-5-(1-propenyl)phenol	HMDB
Vanitrope	HMDB

Chemical Formula

C₁₆H₁₂N₂O₄

Average Molecular Weight

296.2775

Monoisotopic Molecular Weight

296.079706882

IUPAC Name

3-hydroxy-4-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione

Traditional Name

3-hydroxy-4-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione

CAS Registry Number

129724-30-7

SMILES

COC1=C(O)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C23

InChI Identifier

InChI=1S/C16H12N2O4/c1-17-11(19)7-9-8-5-3-4-6-10(8)18-12(9)13(17)15(22-2)14(20)16(18)21/h3-7,20H,1-2H3

InChI Key

CQFOPDQAOBCODL-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
Pyridoindolone
Beta-carboline
Pyridoindole
Diazanaphthalene
Naphthyridine
Indole
Indole or derivatives
Indolizine
Pyrrolopyridine
Alkyl aryl ether
Hydroxypyridine
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Pyrrole
Lactam
Azacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040798)
Cytoplasm (HMDB: HMDB0040798)

Source

Exogenous

Food

Food (HMDB: HMDB0040798)

Not Available

Nutrient (HMDB: HMDB0040798)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 - 254 °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	1.27 g/L	ALOGPS
logP	1.05	ALOGPS
logP	0.14	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	5.69	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.44 m³·mol⁻¹	ChemAxon
Polarizability	29.76 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]+	166.281	31661259
DarkChem	[M-H]-	166.362	31661259
DeepCCS	[M-2H]-	205.305	30932474
DeepCCS	[M+Na]+	180.532	30932474
AllCCS	[M+H]+	164.8	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	168.3	32859911
AllCCS	[M+Na]+	169.3	32859911
AllCCS	[M-H]-	170.4	32859911
AllCCS	[M+Na-2H]-	169.4	32859911
AllCCS	[M+HCOO]-	168.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione	COC1=C(O)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C23	3679.1	Standard polar	33892256
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione	COC1=C(O)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C23	2688.3	Standard non polar	33892256
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione	COC1=C(O)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C23	3003.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione,1TMS,isomer #1	COC1=C(O[Si](C)(C)C)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C32	3084.8	Semi standard non polar	33892256
5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione,1TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C32	3234.1	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-3-methyl-2,6-canthinedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-0090000000-f18fcc70ae2cd3888af2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione GC-MS (1 TMS) - 70eV, Positive	splash10-0uka-2139000000-47259223f378ce840a1a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 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-3-methyl-2,6-canthinedione 10V, Positive-QTOF	splash10-0002-0090000000-03d0a78eadc85e3d2ec2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 20V, Positive-QTOF	splash10-002b-0090000000-e496b4287fadced66a79	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 40V, Positive-QTOF	splash10-004j-0940000000-77d22c5f183d7770885e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 10V, Negative-QTOF	splash10-0002-0090000000-b62122769f7eda50543e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 20V, Negative-QTOF	splash10-0002-0090000000-a9992798466a69d73901	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 40V, Negative-QTOF	splash10-03dr-1590000000-3c1312713ef14deab011	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 10V, Negative-QTOF	splash10-0002-0090000000-8c0a37cb17704175d425	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 20V, Negative-QTOF	splash10-0002-0090000000-8c0a37cb17704175d425	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 40V, Negative-QTOF	splash10-004i-1290000000-1772faac4465b5d9c0e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 10V, Positive-QTOF	splash10-0002-0090000000-5c316f709f7b20344764	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 20V, Positive-QTOF	splash10-0002-0090000000-5c316f709f7b20344764	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione 40V, Positive-QTOF	splash10-0002-0950000000-4a637b057ae6fdd47a1f	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

FDB020614

KNApSAcK ID

Not Available

Chemspider ID

30777512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354280

PDB ID

Not Available

ChEBI ID

174129

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-3-methyl-2,6-canthinedione (HMDB0040798)

MOL for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

3D MOL for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

3D SDF for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

3D-SDF for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

PDB for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

3D PDB for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

SMILES for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

INCHI for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

Structure for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

3D Structure for HMDB0040798 (5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra