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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:44:11 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240249

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tritoqualine

Description

Tritoqualine, also known as hypostamine or inhibostamin, belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide. In humans, tritoqualine is involved in the tritoqualine h1-antihistamine action pathway. Tritoqualine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Tritoqualine.

Structure

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

      72145
  Mrv1652311211718552D          

 36 40  0  0  1  0            999 V2000
    6.4602    0.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2332   -0.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7282   -2.6037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7127    1.6559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5010    2.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0338   -1.5102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1193    2.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0240249
     RDKit          3D
Tritoqualine
 68 72  0  0  0  0  0  0  0  0999 V2000
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M  END

      72145
  Mrv1652311211718552D          

 36 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0240249

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H32N2O8/c1-6-31-23-17-16(18(27)24(32-7-2)25(23)33-8-3)26(29)36-21(17)19-15-13(9-10-28(19)4)11-14-20(22(15)30-5)35-12-34-14/h11,19,21H,6-10,12,27H2,1-5H3

> <INCHI_KEY>
IRGJVQIJENCTQF-UHFFFAOYSA-N

> <FORMULA>
C26H32N2O8

> <MOLECULAR_WEIGHT>
500.548

> <EXACT_MASS>
500.215865998

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.80103588297514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-amino-4,5,6-triethoxy-3-{4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.3145366823333338

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.599026661558884

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.287765393231918

> <JCHEM_PKA_STRONGEST_BASIC>
7.056900810809573

> <JCHEM_POLAR_SURFACE_AREA>
110.94000000000001

> <JCHEM_REFRACTIVITY>
132.4855

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tritoqualine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240249
     RDKit          3D
Tritoqualine
 68 72  0  0  0  0  0  0  0  0999 V2000
    3.3914   -3.5273   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200   -2.3457   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -1.2373    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840   -0.6771    0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859   -1.0555    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -2.0674    2.6021 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752   -0.4430    2.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688    0.5296    1.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859    0.9237    0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6637    1.8933   -0.6750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6751    3.2547   -0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    3.9787   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862    0.3316   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.7020   -1.3536 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2548    1.4973   -1.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438    1.7218   -2.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    0.7922    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -0.3581    1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011   -0.4180   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713   -1.7462   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -2.1036   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898   -1.1188   -2.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416    0.1950   -2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.5191   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966    1.8534   -0.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    2.7090   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456    0.9176   -3.3720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1968    0.1522   -4.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940   -1.1693   -3.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194   -2.7086    0.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0840   -2.1060    2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533   -0.6585    2.0964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -0.0351    3.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406    0.4971    3.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -0.4882    3.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -1.2944    4.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -4.3995   -0.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195   -3.3344    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8758   -3.8926    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1682   -2.6798   -0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -2.1103   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5195   -1.8574    3.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2227   -3.0104    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    3.5771   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334    3.6927    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    5.1036   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    3.8520    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5264    3.7607   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0655    0.8172   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674    2.3722   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950    0.8464   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    2.5915   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013    1.9457   -3.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    1.7857    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740   -1.2304    1.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4771   -3.1376   -1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6992    3.2901   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9941    2.1196    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    3.4115    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2545    0.3959   -3.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012    0.3300   -5.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -3.0726    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -3.6017    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -2.4774    2.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0970   -2.4453    2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1914   -0.1426    3.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822    1.0574    3.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -0.4677    4.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 27  1  0
 27 28  1  0
 28 29  1  0
 20 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 17 34  1  0
 34 35  1  0
 35 36  2  0
 13  4  1  0
 32 18  1  0
 35  7  1  0
 24 19  2  0
 29 22  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  6 42  1  0
  6 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 21 56  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 33 67  1  0
 33 68  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:       72145                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  O   UNK     0      12.059   0.396   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.502  -0.541   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.293  -2.382   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.293  -4.860   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.106  -1.076   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.544   0.983   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.530   3.091   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.535   3.899   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       9.396  -2.819   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.556   4.499   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.792  -2.028   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.809  -0.488   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.168  -2.851   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.396  -4.423   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.168  -4.391   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.792  -5.214   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.581   0.425   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.502  -2.081   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.076   1.883   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.881  -2.546   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.502  -5.161   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.070   0.125   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.835  -2.851   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.606   1.859   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.835  -4.391   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.061   3.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.055   1.283   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.550   2.741   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.191  -3.621   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.835   0.228   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.584  -0.841   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.529   2.141   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.025   3.599   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.620  -2.042   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.019   1.841   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.010   4.757   0.000  0.00  0.00           C+0
CONECT    1   12   24                                                       
CONECT    2   18   30                                                       
CONECT    3   23   29                                                       
CONECT    4   25   29                                                       
CONECT    5   22   31                                                       
CONECT    6   27   32                                                       
CONECT    7   24                                                            
CONECT    8   28   33                                                       
CONECT    9   11   14   20                                                  
CONECT   10   26                                                            
CONECT   11    9   12   13                                                  
CONECT   12    1   11   17                                                  
CONECT   13   11   15   18                                                  
CONECT   14    9   16                                                       
CONECT   15   13   16   21                                                  
CONECT   16   14   15                                                       
CONECT   17   12   19   22                                                  
CONECT   18    2   13   23                                                  
CONECT   19   17   24   26                                                  
CONECT   20    9                                                            
CONECT   21   15   25                                                       
CONECT   22    5   17   27                                                  
CONECT   23    3   18   25                                                  
CONECT   24    1    7   19                                                  
CONECT   25    4   21   23                                                  
CONECT   26   10   19   28                                                  
CONECT   27    6   22   28                                                  
CONECT   28    8   26   27                                                  
CONECT   29    3    4                                                       
CONECT   30    2                                                            
CONECT   31    5   34                                                       
CONECT   32    6   35                                                       
CONECT   33    8   36                                                       
CONECT   34   31                                                            
CONECT   35   32                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0240249
HETATM    1  C1  UNL     1       3.391  -3.527  -0.047  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.120  -2.346  -0.615  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.076  -1.237   0.241  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.884  -0.677   0.611  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.186  -1.056   1.733  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.674  -2.067   2.602  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.975  -0.443   2.048  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.469   0.530   1.240  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.186   0.924   0.094  1.00  0.00           C  
HETATM   10  O2  UNL     1       0.664   1.893  -0.675  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.675   3.255  -0.688  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.969   3.979  -0.804  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.386   0.332  -0.230  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.093   0.702  -1.354  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.255   1.497  -1.384  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.744   1.722  -2.801  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.933   0.792   1.764  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.763  -0.358   1.321  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.301  -0.418  -0.033  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.671  -1.746  -0.350  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.200  -2.104  -1.553  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.390  -1.119  -2.519  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.042   0.195  -2.239  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.497   0.519  -0.980  1.00  0.00           C  
HETATM   25  O4  UNL     1      -2.197   1.853  -0.794  1.00  0.00           O  
HETATM   26  C21 UNL     1      -3.214   2.709  -0.268  1.00  0.00           C  
HETATM   27  O5  UNL     1      -3.346   0.918  -3.372  1.00  0.00           O  
HETATM   28  C22 UNL     1      -4.197   0.152  -4.231  1.00  0.00           C  
HETATM   29  O6  UNL     1      -3.894  -1.169  -3.810  1.00  0.00           O  
HETATM   30  C23 UNL     1      -2.519  -2.709   0.794  1.00  0.00           C  
HETATM   31  C24 UNL     1      -3.084  -2.106   2.081  1.00  0.00           C  
HETATM   32  N2  UNL     1      -2.953  -0.659   2.096  1.00  0.00           N  
HETATM   33  C25 UNL     1      -3.102  -0.035   3.335  1.00  0.00           C  
HETATM   34  O7  UNL     1      -0.741   0.497   3.143  1.00  0.00           O  
HETATM   35  C26 UNL     1       0.189  -0.488   3.290  1.00  0.00           C  
HETATM   36  O8  UNL     1       0.389  -1.294   4.246  1.00  0.00           O  
HETATM   37  H1  UNL     1       3.406  -4.399  -0.765  1.00  0.00           H  
HETATM   38  H2  UNL     1       2.320  -3.334   0.147  1.00  0.00           H  
HETATM   39  H3  UNL     1       3.876  -3.893   0.873  1.00  0.00           H  
HETATM   40  H4  UNL     1       5.168  -2.680  -0.816  1.00  0.00           H  
HETATM   41  H5  UNL     1       3.695  -2.110  -1.615  1.00  0.00           H  
HETATM   42  H6  UNL     1       3.519  -1.857   3.198  1.00  0.00           H  
HETATM   43  H7  UNL     1       2.223  -3.010   2.669  1.00  0.00           H  
HETATM   44  H8  UNL     1       0.073   3.577  -1.605  1.00  0.00           H  
HETATM   45  H9  UNL     1       0.033   3.693   0.147  1.00  0.00           H  
HETATM   46  H10 UNL     1       1.816   5.104  -0.836  1.00  0.00           H  
HETATM   47  H11 UNL     1       2.622   3.852   0.094  1.00  0.00           H  
HETATM   48  H12 UNL     1       2.526   3.761  -1.715  1.00  0.00           H  
HETATM   49  H13 UNL     1       5.065   0.817  -0.937  1.00  0.00           H  
HETATM   50  H14 UNL     1       4.267   2.372  -0.745  1.00  0.00           H  
HETATM   51  H15 UNL     1       5.295   0.846  -3.181  1.00  0.00           H  
HETATM   52  H16 UNL     1       5.412   2.592  -2.815  1.00  0.00           H  
HETATM   53  H17 UNL     1       3.901   1.946  -3.492  1.00  0.00           H  
HETATM   54  H18 UNL     1      -1.275   1.786   1.668  1.00  0.00           H  
HETATM   55  H19 UNL     1      -1.074  -1.230   1.471  1.00  0.00           H  
HETATM   56  H20 UNL     1      -3.477  -3.138  -1.778  1.00  0.00           H  
HETATM   57  H21 UNL     1      -3.699   3.290  -1.089  1.00  0.00           H  
HETATM   58  H22 UNL     1      -3.994   2.120   0.249  1.00  0.00           H  
HETATM   59  H23 UNL     1      -2.797   3.411   0.482  1.00  0.00           H  
HETATM   60  H24 UNL     1      -5.254   0.396  -3.938  1.00  0.00           H  
HETATM   61  H25 UNL     1      -4.001   0.330  -5.289  1.00  0.00           H  
HETATM   62  H26 UNL     1      -1.506  -3.073   0.867  1.00  0.00           H  
HETATM   63  H27 UNL     1      -3.172  -3.602   0.601  1.00  0.00           H  
HETATM   64  H28 UNL     1      -2.419  -2.477   2.899  1.00  0.00           H  
HETATM   65  H29 UNL     1      -4.097  -2.445   2.300  1.00  0.00           H  
HETATM   66  H30 UNL     1      -4.191  -0.143   3.639  1.00  0.00           H  
HETATM   67  H31 UNL     1      -2.982   1.057   3.216  1.00  0.00           H  
HETATM   68  H32 UNL     1      -2.561  -0.468   4.201  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3   40   41
CONECT    3    4
CONECT    4    5    5   13
CONECT    5    6    7
CONECT    6   42   43
CONECT    7    8    8   35
CONECT    8    9   17
CONECT    9   10   13   13
CONECT   10   11
CONECT   11   12   44   45
CONECT   12   46   47   48
CONECT   13   14
CONECT   14   15
CONECT   15   16   49   50
CONECT   16   51   52   53
CONECT   17   18   34   54
CONECT   18   19   32   55
CONECT   19   20   24   24
CONECT   20   21   21   30
CONECT   21   22   56
CONECT   22   23   23   29
CONECT   23   24   27
CONECT   24   25
CONECT   25   26
CONECT   26   57   58   59
CONECT   27   28
CONECT   28   29   60   61
CONECT   30   31   62   63
CONECT   31   32   64   65
CONECT   32   33
CONECT   33   66   67   68
CONECT   34   35
CONECT   35   36   36
END

HMDB0240249
     RDKit          3D
Tritoqualine
 68 72  0  0  0  0  0  0  0  0999 V2000
    3.3914   -3.5273   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200   -2.3457   -0.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0760   -1.2373    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8840   -0.6771    0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859   -1.0555    1.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6740   -2.0674    2.6021 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752   -0.4430    2.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4688    0.5296    1.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1859    0.9237    0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6637    1.8933   -0.6750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6751    3.2547   -0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    3.9787   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862    0.3316   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0932    0.7020   -1.3536 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2548    1.4973   -1.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7438    1.7218   -2.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333    0.7922    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -0.3581    1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011   -0.4180   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6713   -1.7462   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997   -2.1036   -1.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3898   -1.1188   -2.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0416    0.1950   -2.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.5191   -0.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1966    1.8534   -0.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    2.7090   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456    0.9176   -3.3720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1968    0.1522   -4.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940   -1.1693   -3.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194   -2.7086    0.7939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0840   -2.1060    2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9533   -0.6585    2.0964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -0.0351    3.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7406    0.4971    3.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -0.4882    3.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -1.2944    4.2460 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -4.3995   -0.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3195   -3.3344    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8758   -3.8926    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1682   -2.6798   -0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945   -2.1103   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5195   -1.8574    3.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2227   -3.0104    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729    3.5771   -1.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334    3.6927    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    5.1036   -0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    3.8520    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5264    3.7607   -1.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0655    0.8172   -0.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2674    2.3722   -0.7446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950    0.8464   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    2.5915   -2.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013    1.9457   -3.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    1.7857    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0740   -1.2304    1.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4771   -3.1376   -1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6992    3.2901   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9941    2.1196    0.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7974    3.4115    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2545    0.3959   -3.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012    0.3300   -5.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056   -3.0726    0.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -3.6017    0.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -2.4774    2.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0970   -2.4453    2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1914   -0.1426    3.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822    1.0574    3.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607   -0.4677    4.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 27  1  0
 27 28  1  0
 28 29  1  0
 20 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 17 34  1  0
 34 35  1  0
 35 36  2  0
 13  4  1  0
 32 18  1  0
 35  7  1  0
 24 19  2  0
 29 22  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  6 42  1  0
  6 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 21 56  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  0
 30 63  1  0
 31 64  1  0
 31 65  1  0
 33 66  1  0
 33 67  1  0
 33 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hypostamine	Kegg
35NZ	HMDB
554l	HMDB
Hypostamin	HMDB
Inhibostamin	HMDB
L 554	HMDB
Livalfa	HMDB
Tritocaline	HMDB
4,5,6-Triethoxy-7-amino-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)phthalide	HMDB
Chiesi brand OF tritoqualine	HMDB
Tritoqualin	HMDB
Tritoqualine	HMDB

Chemical Formula

C₂₆H₃₂N₂O₈

Average Molecular Weight

500.548

Monoisotopic Molecular Weight

500.215865998

IUPAC Name

7-amino-4,5,6-triethoxy-3-{4-methoxy-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-1,3-dihydro-2-benzofuran-1-one

Traditional Name

tritoqualine

CAS Registry Number

14504-73-5

SMILES

CCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12

InChI Identifier

InChI=1S/C26H32N2O8/c1-6-31-23-17-16(18(27)24(32-7-2)25(23)33-8-3)26(29)36-21(17)19-15-13(9-10-28(19)4)11-14-20(22(15)30-5)35-12-34-14/h11,19,21H,6-10,12,27H2,1-5H3

InChI Key

IRGJVQIJENCTQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Phthalide isoquinolines

Sub Class

Not Available

Direct Parent

Phthalide isoquinolines

Alternative Parents

Substituents

Phthalide isoquinoline
Gallic acid or derivatives
Benzofuranone
Isobenzofuranone
Phthalide
Tetrahydroisoquinoline
Benzodioxole
Isocoumaran
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Vinylogous amide
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Lactone
Carboxylic acid ester
Azacycle
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Primary amine
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	2.65	ALOGPS
logP	3.31	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	7.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.94 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.49 m³·mol⁻¹	ChemAxon
Polarizability	52.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	220.3	31661259
AllCCS	[M+H]+	216.865	31661259
DeepCCS	[M-2H]-	241.697	30932474
DeepCCS	[M+Na]+	217.122	30932474
AllCCS	[M+H]+	216.9	32859911
AllCCS	[M+H-H2O]+	214.9	32859911
AllCCS	[M+NH4]+	218.7	32859911
AllCCS	[M+Na]+	219.2	32859911
AllCCS	[M-H]-	220.3	32859911
AllCCS	[M+Na-2H]-	221.3	32859911
AllCCS	[M+HCOO]-	222.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tritoqualine	CCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12	4880.8	Standard polar	33892256
Tritoqualine	CCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12	3816.8	Standard non polar	33892256
Tritoqualine	CCOC1=C(OCC)C(OCC)=C(N)C2=C1C(OC2=O)C1N(C)CCC2=CC3=C(OCO3)C(OC)=C12	3602.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tritoqualine,1TMS,isomer #1	CCOC1=C(N[Si](C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O	3715.4	Semi standard non polar	33892256
Tritoqualine,1TMS,isomer #1	CCOC1=C(N[Si](C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O	3481.3	Standard non polar	33892256
Tritoqualine,1TMS,isomer #1	CCOC1=C(N[Si](C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O	5067.9	Standard polar	33892256
Tritoqualine,2TMS,isomer #1	CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C)[Si](C)(C)C)=C1OCC	3735.7	Semi standard non polar	33892256
Tritoqualine,2TMS,isomer #1	CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C)[Si](C)(C)C)=C1OCC	3615.2	Standard non polar	33892256
Tritoqualine,2TMS,isomer #1	CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C)[Si](C)(C)C)=C1OCC	4750.1	Standard polar	33892256
Tritoqualine,1TBDMS,isomer #1	CCOC1=C(N[Si](C)(C)C(C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O	3870.7	Semi standard non polar	33892256
Tritoqualine,1TBDMS,isomer #1	CCOC1=C(N[Si](C)(C)C(C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O	3659.5	Standard non polar	33892256
Tritoqualine,1TBDMS,isomer #1	CCOC1=C(N[Si](C)(C)C(C)(C)C)C2=C(C(OCC)=C1OCC)C(C1C3=C(OC)C4=C(C=C3CCN1C)OCO4)OC2=O	5107.4	Standard polar	33892256
Tritoqualine,2TBDMS,isomer #1	CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1OCC	3994.5	Semi standard non polar	33892256
Tritoqualine,2TBDMS,isomer #1	CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1OCC	3963.2	Standard non polar	33892256
Tritoqualine,2TBDMS,isomer #1	CCOC1=C(OCC)C2=C(C(=O)OC2C2C3=C(OC)C4=C(C=C3CCN2C)OCO4)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1OCC	4833.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 10V, Positive-QTOF	splash10-0udi-0000970000-2073e34843dbe1f78ccf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 20V, Positive-QTOF	splash10-0kn9-0170910000-e6c4f40e34955b456ff9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 40V, Positive-QTOF	splash10-0f80-0090000000-7cc49a686e10da15139a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 10V, Negative-QTOF	splash10-0002-0000900000-290845d9729e8a80a7ce	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 20V, Negative-QTOF	splash10-056r-0010900000-8c440296c4d90628f854	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 40V, Negative-QTOF	splash10-0007-5309800000-acf5193382ea7b5f682b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 10V, Negative-QTOF	splash10-0002-0000900000-4d069a52fe971059afe4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 20V, Negative-QTOF	splash10-0002-0000900000-fadeb483bbec9fb9d0ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 40V, Negative-QTOF	splash10-0a6u-0000900000-d7bc9e993995d947cd0e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 10V, Positive-QTOF	splash10-0udi-0000090000-b9e3b6ce832a852588dc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 20V, Positive-QTOF	splash10-0udi-0010290000-16dc28435713e30f6b64	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tritoqualine 40V, Positive-QTOF	splash10-00dl-0270900000-acd5df7fb82c34294600	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tritoqualine H1-Antihistamine Action		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13711

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

65119

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tritoqualine

METLIN ID

Not Available

PubChem Compound

72145

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

Umezu K, Yuasa S, Ichikawa A: Inhibitory mechanism of tritoqualine on histamine release from mast cells. Biochem Pharmacol. 1986 Sep 15;35(18):3137-42. [PubMed:2428378 ]

Showing metabocard for Tritoqualine (HMDB0240249)

MOL for HMDB0240249 (Tritoqualine)

3D MOL for HMDB0240249 (Tritoqualine)

3D SDF for HMDB0240249 (Tritoqualine)

3D-SDF for HMDB0240249 (Tritoqualine)

PDB for HMDB0240249 (Tritoqualine)

3D PDB for HMDB0240249 (Tritoqualine)

SMILES for HMDB0240249 (Tritoqualine)

INCHI for HMDB0240249 (Tritoqualine)

Structure for HMDB0240249 (Tritoqualine)

3D Structure for HMDB0240249 (Tritoqualine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra