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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:13 UTC

Update Date

2019-07-23 07:15:13 UTC

HMDB ID

HMDB0060847

Secondary Accession Numbers

HMDB60847

Metabolite Identification

Common Name

N-Monodesmethyl-rizatriptan

Description

N-Monodesmethyl-rizatriptan is a metabolite of rizatriptan. Rizatriptan (Maxalt) is a 5-HT1 agonist triptan drug developed by Merck & Co. for the treatment of migraine headaches. It is available in strengths of 5 and 10 mg as tablets and orally disintegrating tablets (Maxalt-MLT). Maxalt obtained approval by the United States Food and Drug Administration (FDA) on June 29, 1998. It is a second-generation triptan. Rizatriptan is available only by prescription in Australia, the United States, Canada and New Zealand. (Wikipedia)

Structure

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

HMDB0060847
     RDKit          3D
N-Monodesmethyl-rizatriptan
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.0342    0.6621   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    0.5287    0.7984 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493    1.2747    1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.7610    1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -1.5521    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -1.7506    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432   -2.7003   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -2.4877   -2.0408 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -1.4105   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -0.8051   -2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714    0.2939   -2.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    0.9306   -2.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5932    0.7433   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.8420   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5943    1.3027    0.3580 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2562   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6397    0.6658    0.6751 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9436    0.3411    1.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6771    0.7357    1.5727 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138    0.1105   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0560   -0.9530   -0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578   -0.1373   -1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.6866   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405    1.6773   -0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.5446    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0674    0.6419    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2337    2.1886    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3147   -0.7223    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7828   -1.4263    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468   -1.0572    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -2.5670    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -3.5008   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -3.0269   -2.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -1.1710   -3.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762    1.7467   -2.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    2.6286   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.2679    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0906    1.6541   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -0.1565    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.4619    0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  2  0
 21  6  1  0
 21  9  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 20 40  1  0
M  END


  Mrv0541 07041312032D          

 21 23  0  0  0  0            999 V2000
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7342   -2.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -3.6175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6543   -3.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3993   -2.8329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 21  1  0  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060847

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC1=CNC2=CC(O)=C(CN3C=NC=N3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H19N5O/c1-19(2)4-3-11-7-17-14-6-15(21)12(5-13(11)14)8-20-10-16-9-18-20/h5-7,9-10,17,21H,3-4,8H2,1-2H3

> <INCHI_KEY>
YQPPJBHQJWSUTE-UHFFFAOYSA-N

> <FORMULA>
C15H19N5O

> <MOLECULAR_WEIGHT>
285.3443

> <EXACT_MASS>
285.158960255

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.89193583367166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(dimethylamino)ethyl]-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-6-ol

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.6701890105990742

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.131761804786347

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.177457731786088

> <JCHEM_PKA_STRONGEST_BASIC>
9.806972380264558

> <JCHEM_POLAR_SURFACE_AREA>
69.97

> <JCHEM_REFRACTIVITY>
95.11319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(dimethylamino)ethyl]-5-(1,2,4-triazol-1-ylmethyl)-1H-indol-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060847
     RDKit          3D
N-Monodesmethyl-rizatriptan
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.0342    0.6621   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    0.5287    0.7984 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493    1.2747    1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.7610    1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -1.5521    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -1.7506    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432   -2.7003   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -2.4877   -2.0408 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -1.4105   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -0.8051   -2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714    0.2939   -2.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    0.9306   -2.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5932    0.7433   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.8420   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5943    1.3027    0.3580 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2562   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6397    0.6658    0.6751 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9436    0.3411    1.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6771    0.7357    1.5727 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138    0.1105   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0560   -0.9530   -0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578   -0.1373   -1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.6866   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405    1.6773   -0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.5446    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0674    0.6419    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2337    2.1886    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3147   -0.7223    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7828   -1.4263    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468   -1.0572    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -2.5670    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -3.5008   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -3.0269   -2.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -1.1710   -3.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762    1.7467   -2.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    2.6286   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.2679    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0906    1.6541   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -0.1565    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.4619    0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  2  0
 21  6  1  0
 21  9  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.332  -5.798   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.143  -4.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       7.591  -4.383   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       8.837  -5.288   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.361  -6.753   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.821  -6.753   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.345  -5.288   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   13   21                                                       
CONECT   21   20    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060847
HETATM    1  C1  UNL     1      -3.034   0.662  -0.617  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.020   0.529   0.798  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.149   1.275   1.321  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.966  -0.761   1.329  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.687  -1.552   1.304  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.050  -1.751   0.003  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.343  -2.700  -0.952  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.583  -2.488  -2.041  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.232  -1.411  -1.857  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.187  -0.805  -2.651  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.871   0.294  -2.130  1.00  0.00           C  
HETATM   12  O1  UNL     1       2.839   0.931  -2.927  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.593   0.743  -0.870  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.330   1.842  -0.197  1.00  0.00           C  
HETATM   15  N3  UNL     1       3.594   1.303   0.358  1.00  0.00           N  
HETATM   16  C12 UNL     1       4.807   1.256  -0.189  1.00  0.00           C  
HETATM   17  N4  UNL     1       5.640   0.666   0.675  1.00  0.00           N  
HETATM   18  C13 UNL     1       4.944   0.341   1.770  1.00  0.00           C  
HETATM   19  N5  UNL     1       3.677   0.736   1.573  1.00  0.00           N  
HETATM   20  C14 UNL     1       0.614   0.111  -0.092  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.056  -0.953  -0.588  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.558  -0.137  -1.171  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.095   0.687  -1.030  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.641   1.677  -0.874  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.034   1.545   2.372  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.067   0.642   1.125  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.234   2.189   0.662  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.315  -0.722   2.438  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.783  -1.426   0.898  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.947  -1.057   2.041  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.907  -2.567   1.765  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.079  -3.501  -0.836  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.556  -3.027  -2.943  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.393  -1.171  -3.640  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.276   1.747  -2.565  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.536   2.629  -0.940  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.745   2.268   0.626  1.00  0.00           H  
HETATM   38  H17 UNL     1       5.091   1.654  -1.187  1.00  0.00           H  
HETATM   39  H18 UNL     1       5.346  -0.156   2.675  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.389   0.462   0.918  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7    7   21
CONECT    7    8   32
CONECT    8    9   33
CONECT    9   10   10   21
CONECT   10   11   34
CONECT   11   12   13   13
CONECT   12   35
CONECT   13   14   20
CONECT   14   15   36   37
CONECT   15   16   19
CONECT   16   17   17   38
CONECT   17   18
CONECT   18   19   19   39
CONECT   20   21   21   40
END

HMDB0060847
     RDKit          3D
N-Monodesmethyl-rizatriptan
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.0342    0.6621   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    0.5287    0.7984 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493    1.2747    1.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9658   -0.7610    1.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -1.5521    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -1.7506    0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432   -2.7003   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -2.4877   -2.0408 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -1.4105   -1.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -0.8051   -2.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8714    0.2939   -2.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8391    0.9306   -2.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5932    0.7433   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    1.8420   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5943    1.3027    0.3580 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8070    1.2562   -0.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6397    0.6658    0.6751 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9436    0.3411    1.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6771    0.7357    1.5727 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6138    0.1105   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0560   -0.9530   -0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5578   -0.1373   -1.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0949    0.6866   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6405    1.6773   -0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.5446    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0674    0.6419    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2337    2.1886    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3147   -0.7223    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7828   -1.4263    0.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9468   -1.0572    2.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9066   -2.5670    1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -3.5008   -0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -3.0269   -2.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -1.1710   -3.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762    1.7467   -2.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    2.6286   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.2679    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0906    1.6541   -1.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3460   -0.1565    2.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    0.4619    0.9181 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  2  0
 21  6  1  0
 21  9  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉N₅O

Average Molecular Weight

285.3443

Monoisotopic Molecular Weight

285.158960255

IUPAC Name

3-[2-(dimethylamino)ethyl]-5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-6-ol

Traditional Name

3-[2-(dimethylamino)ethyl]-5-(1,2,4-triazol-1-ylmethyl)-1H-indol-6-ol

CAS Registry Number

Not Available

SMILES

CN(C)CCC1=CNC2=CC(O)=C(CN3C=NC=N3)C=C12

InChI Identifier

InChI=1S/C15H19N5O/c1-19(2)4-3-11-7-17-14-6-15(21)12(5-13(11)14)8-20-10-16-9-18-20/h5-7,9-10,17,21H,3-4,8H2,1-2H3

InChI Key

YQPPJBHQJWSUTE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Substituted pyrrole
Benzenoid
Azole
Pyrrole
1,2,4-triazole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060847)

Organ

Kidney (HMDB: HMDB0060847)
Liver (HMDB: HMDB0060847)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060847)

Cellular substructure

Cytoplasm (HMDB: HMDB0060847)

Source

Endogenous

Endogenous (HMDB: HMDB0060847)

Process

Not Available

Role

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
Water Solubility	0.65 g/L	ALOGPS
logP	0.9	ALOGPS
logP	0.67	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	9.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.11 m³·mol⁻¹	ChemAxon
Polarizability	30.89 Å³	ChemAxon
Number of Rings	3	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]+	167.482	31661259
DarkChem	[M-H]-	165.992	31661259
DeepCCS	[M-2H]-	201.517	30932474
DeepCCS	[M+Na]+	177.082	30932474
AllCCS	[M+H]+	167.8	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	171.0	32859911
AllCCS	[M+Na]+	171.9	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	172.4	32859911
AllCCS	[M+HCOO]-	172.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.5 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4052 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.13 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	515.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	81.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	268.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	264.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	845.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	607.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	989.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	681.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	502.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	115.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Monodesmethyl-rizatriptan	CN(C)CCC1=CNC2=CC(O)=C(CN3C=NC=N3)C=C12	3629.5	Standard polar	33892256
N-Monodesmethyl-rizatriptan	CN(C)CCC1=CNC2=CC(O)=C(CN3C=NC=N3)C=C12	2736.5	Standard non polar	33892256
N-Monodesmethyl-rizatriptan	CN(C)CCC1=CNC2=CC(O)=C(CN3C=NC=N3)C=C12	2931.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Monodesmethyl-rizatriptan,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC(O[Si](C)(C)C)=C(CN3C=NC=N3)C=C12	2692.4	Semi standard non polar	33892256
N-Monodesmethyl-rizatriptan,1TMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C)C2=CC(O)=C(CN3C=NC=N3)C=C12	2748.5	Semi standard non polar	33892256
N-Monodesmethyl-rizatriptan,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=C(CN3C=NC=N3)C=C12	2744.7	Semi standard non polar	33892256
N-Monodesmethyl-rizatriptan,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=C(CN3C=NC=N3)C=C12	2869.0	Standard non polar	33892256
N-Monodesmethyl-rizatriptan,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=C(CN3C=NC=N3)C=C12	3421.6	Standard polar	33892256
N-Monodesmethyl-rizatriptan,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC(O[Si](C)(C)C(C)(C)C)=C(CN3C=NC=N3)C=C12	2925.4	Semi standard non polar	33892256
N-Monodesmethyl-rizatriptan,1TBDMS,isomer #2	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O)=C(CN3C=NC=N3)C=C12	2962.7	Semi standard non polar	33892256
N-Monodesmethyl-rizatriptan,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=C(CN3C=NC=N3)C=C12	3142.4	Semi standard non polar	33892256
N-Monodesmethyl-rizatriptan,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=C(CN3C=NC=N3)C=C12	3199.3	Standard non polar	33892256
N-Monodesmethyl-rizatriptan,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=C(CN3C=NC=N3)C=C12	3523.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodesmethyl-rizatriptan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9040000000-cc9d0c3990d85169fe8e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodesmethyl-rizatriptan GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9032000000-5dcc4e86ffb18ee78238	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodesmethyl-rizatriptan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Monodesmethyl-rizatriptan 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 - N-Monodesmethyl-rizatriptan 10V, Positive-QTOF	splash10-000i-0090000000-d34f4ebf82818d6fa5f1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 20V, Positive-QTOF	splash10-00kf-1190000000-00d2e3f3293c4a967295	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 40V, Positive-QTOF	splash10-05fr-9830000000-331b1851952a8cb2552a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 10V, Negative-QTOF	splash10-0159-9070000000-96ac9a003b8286039654	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 20V, Negative-QTOF	splash10-014i-9060000000-ab447f1fd75c4ed91deb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 40V, Negative-QTOF	splash10-016u-9000000000-10bde99b17f05c7d8dcb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 10V, Positive-QTOF	splash10-000i-2090000000-4d6af15b9d65e66bc085	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 20V, Positive-QTOF	splash10-0ab9-9360000000-1e7564db2fd621466fc7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 40V, Positive-QTOF	splash10-0ab9-9100000000-3839ea2f74693521b4b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 10V, Negative-QTOF	splash10-001i-0090000000-4542905bc56c1659deb6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 20V, Negative-QTOF	splash10-0159-9160000000-e13ce79ab60f295436ca	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Monodesmethyl-rizatriptan 40V, Negative-QTOF	splash10-014i-9000000000-734694574ceabd95f85a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11742124

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

Not Available

Showing metabocard for N-Monodesmethyl-rizatriptan (HMDB0060847)

MOL for HMDB0060847 (N-Monodesmethyl-rizatriptan)

3D MOL for HMDB0060847 (N-Monodesmethyl-rizatriptan)

3D SDF for HMDB0060847 (N-Monodesmethyl-rizatriptan)

3D-SDF for HMDB0060847 (N-Monodesmethyl-rizatriptan)

PDB for HMDB0060847 (N-Monodesmethyl-rizatriptan)

3D PDB for HMDB0060847 (N-Monodesmethyl-rizatriptan)

SMILES for HMDB0060847 (N-Monodesmethyl-rizatriptan)

INCHI for HMDB0060847 (N-Monodesmethyl-rizatriptan)

Structure for HMDB0060847 (N-Monodesmethyl-rizatriptan)

3D Structure for HMDB0060847 (N-Monodesmethyl-rizatriptan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra