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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-17 11:10:02 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005037

Secondary Accession Numbers

HMDB05037

Metabolite Identification

Common Name

Sumatriptan

Description

Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve. Sumatriptan is a triptan drug including a sulfonamide group structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraines. Sumatriptan (Imitrex, Imigran, Imigran Recovery) is a triptan drug including a sulfonamide group which was originally developed by Glaxo for the treatment of migraine headaches.

Structure

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

HMDB0005037
     RDKit          3D
Sumatriptan
 41 42  0  0  0  0  0  0  0  0999 V2000
    4.0052    1.0378    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985    0.9027   -1.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126    0.4021   -2.1896 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.1204    1.4401   -2.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673    0.3621   -3.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5206   -1.1794   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -1.3567   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -1.8665    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620   -2.0554    1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190   -1.7111    1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -1.7882    2.9042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -1.3475    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3899   -0.9706    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304   -0.4199    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942    1.0675    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    1.7400   -0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2928    1.3284   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6447    1.5368    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.2034    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -1.0312   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602    1.9945    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.9771    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542    0.2264    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147    0.4407   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -1.9599   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -1.4411   -2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -2.1387    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470   -2.4605    2.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226   -2.1429    3.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779   -1.2904    3.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446   -0.6002    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -0.8945   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422    1.1905   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    1.5608    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290    0.4538   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7513    2.1608   -2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    1.2262   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5581    1.3293    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025    2.4897    0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    0.7214   -0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0779   -0.6272   -1.2247 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
  3  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 13 19  1  0
 19 20  2  0
 20  7  1  0
 19 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
M  END

669
  Mrv0541 02231214552D          

 20 21  0  0  0  0            999 V2000
    3.0791   -0.5207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -1.2351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -1.5972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0375    1.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9739    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7812    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -0.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8448    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  5 19  1  0  0  0  0
  6 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 14  2  0  0  0  0
  8 10  2  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
 10 16  1  0  0  0  0
 11 13  2  0  0  0  0
 11 15  1  0  0  0  0
 11 17  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005037

> <DATABASE_NAME>
hmdb

> <SMILES>
CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

> <INCHI_KEY>
KQKPFRSPSRPDEB-UHFFFAOYSA-N

> <FORMULA>
C14H21N3O2S

> <MOLECULAR_WEIGHT>
295.4

> <EXACT_MASS>
295.135447621

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.30534147835603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.7419288613400098

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.140195724720275

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.244987975521886

> <JCHEM_PKA_STRONGEST_BASIC>
9.536988551879368

> <JCHEM_POLAR_SURFACE_AREA>
65.2

> <JCHEM_REFRACTIVITY>
82.08419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sumatriptan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005037
     RDKit          3D
Sumatriptan
 41 42  0  0  0  0  0  0  0  0999 V2000
    4.0052    1.0378    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985    0.9027   -1.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126    0.4021   -2.1896 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.1204    1.4401   -2.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673    0.3621   -3.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5206   -1.1794   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -1.3567   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -1.8665    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620   -2.0554    1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190   -1.7111    1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -1.7882    2.9042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -1.3475    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3899   -0.9706    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304   -0.4199    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942    1.0675    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    1.7400   -0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2928    1.3284   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6447    1.5368    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.2034    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -1.0312   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602    1.9945    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.9771    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542    0.2264    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147    0.4407   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -1.9599   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -1.4411   -2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -2.1387    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470   -2.4605    2.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226   -2.1429    3.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779   -1.2904    3.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446   -0.6002    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -0.8945   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422    1.1905   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    1.5608    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290    0.4538   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7513    2.1608   -2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    1.2262   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5581    1.3293    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025    2.4897    0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    0.7214   -0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0779   -0.6272   -1.2247 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
  3  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 13 19  1  0
 19 20  2  0
 20  7  1  0
 19 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 669                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.748  -0.972   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.518  -2.306   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.977   0.362   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      12.540  -2.981   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      15.003   2.743   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.414  -1.742   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.540  -0.503   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082  -0.972   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.018   0.961   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082  -2.512   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -0.972   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.525   1.279   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -0.202   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.438  -1.742   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -0.202   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -3.282   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -2.512   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.510   3.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.975   3.889   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -0.972   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   15                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   10   14                                                       
CONECT    5   12   18   19                                                  
CONECT    6    1   20                                                       
CONECT    7    8    9   14                                                  
CONECT    8    7   10   13                                                  
CONECT    9    7   12                                                       
CONECT   10    4    8   16                                                  
CONECT   11   13   15   17                                                  
CONECT   12    5    9                                                       
CONECT   13    8   11                                                       
CONECT   14    4    7                                                       
CONECT   15    1   11                                                       
CONECT   16   10   17                                                       
CONECT   17   11   16                                                       
CONECT   18    5                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0005037
HETATM    1  C1  UNL     1       4.005   1.038   0.269  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.399   0.903  -1.094  1.00  0.00           N  
HETATM    3  S1  UNL     1       3.213   0.402  -2.190  1.00  0.00           S  
HETATM    4  O1  UNL     1       2.120   1.440  -2.321  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.867   0.362  -3.569  1.00  0.00           O  
HETATM    6  C2  UNL     1       2.521  -1.179  -1.914  1.00  0.00           C  
HETATM    7  C3  UNL     1       1.845  -1.357  -0.614  1.00  0.00           C  
HETATM    8  C4  UNL     1       2.542  -1.866   0.459  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.962  -2.055   1.695  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.619  -1.711   1.842  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.175  -1.788   2.904  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.406  -1.348   2.604  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.390  -0.971   1.280  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.530  -0.420   0.508  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.294   1.068   0.371  1.00  0.00           C  
HETATM   16  N3  UNL     1      -3.329   1.740  -0.359  1.00  0.00           N  
HETATM   17  C11 UNL     1      -3.293   1.328  -1.745  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.645   1.537   0.210  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.116  -1.203   0.814  1.00  0.00           C  
HETATM   20  C14 UNL     1       0.515  -1.031  -0.414  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.360   1.995   0.729  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.903   0.977   0.381  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.454   0.226   0.862  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.315   0.441  -1.225  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.319  -1.960  -2.065  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.744  -1.441  -2.692  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.584  -2.139   0.361  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.547  -2.461   2.519  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.123  -2.143   3.839  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.278  -1.290   3.276  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.445  -0.600   1.071  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.583  -0.894  -0.484  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.342   1.191  -0.199  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.143   1.561   1.343  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.929   0.454  -1.876  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.751   2.161  -2.333  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.260   1.226  -2.105  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.558   1.329   1.283  1.00  0.00           H  
HETATM   39  H19 UNL     1      -5.203   2.490   0.092  1.00  0.00           H  
HETATM   40  H20 UNL     1      -5.208   0.721  -0.288  1.00  0.00           H  
HETATM   41  H21 UNL     1      -0.078  -0.627  -1.225  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24
CONECT    3    4    4    5    5
CONECT    3    6
CONECT    6    7   25   26
CONECT    7    8    8   20
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   19
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   19
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   18
CONECT   17   35   36   37
CONECT   18   38   39   40
CONECT   19   20   20
CONECT   20   41
END

HMDB0005037
     RDKit          3D
Sumatriptan
 41 42  0  0  0  0  0  0  0  0999 V2000
    4.0052    1.0378    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985    0.9027   -1.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126    0.4021   -2.1896 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.1204    1.4401   -2.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673    0.3621   -3.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5206   -1.1794   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -1.3567   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -1.8665    0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620   -2.0554    1.6946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6190   -1.7111    1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -1.7882    2.9042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -1.3475    2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3899   -0.9706    1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5304   -0.4199    0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942    1.0675    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    1.7400   -0.3595 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2928    1.3284   -1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6447    1.5368    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.2034    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -1.0312   -0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3602    1.9945    0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.9771    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542    0.2264    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147    0.4407   -1.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186   -1.9599   -2.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -1.4411   -2.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842   -2.1387    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470   -2.4605    2.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1226   -2.1429    3.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2779   -1.2904    3.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446   -0.6002    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -0.8945   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3422    1.1905   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    1.5608    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9290    0.4538   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7513    2.1608   -2.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2604    1.2262   -2.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5581    1.3293    1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2025    2.4897    0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    0.7214   -0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0779   -0.6272   -1.2247 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
  3  5  2  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 13 19  1  0
 19 20  2  0
 20  7  1  0
 19 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 20 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide	ChEBI
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide	ChEBI
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide	ChEBI
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide	ChEBI
Imigran	ChEBI
Imitrex	ChEBI
Sumatran	ChEBI
Sumatriptanum	ChEBI
Sumax	ChEBI
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamide	Generator
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamide	Generator
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulphonamide	Generator
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulphonamide	Generator
Imigran recovery	HMDB
Glaxo wellcome brand OF sumatriptan	HMDB
Sumatriptan GSK brand	HMDB
GSK Brand OF sumatriptan	HMDB
Sumatriptan succinate	HMDB
Succinate, sumatriptan	HMDB

Chemical Formula

C₁₄H₂₁N₃O₂S

Average Molecular Weight

295.4

Monoisotopic Molecular Weight

295.135447621

IUPAC Name

1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

Traditional Name

sumatriptan

CAS Registry Number

103628-46-2

SMILES

CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI Identifier

InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

InChI Key

KQKPFRSPSRPDEB-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
3-alkylindole
Indole
Aralkylamine
Substituted pyrrole
Organic sulfonic acid amide
Benzenoid
Organosulfonic acid amide
Pyrrole
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:10650 )
tryptamines (CHEBI:10650 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	169 - 171 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.93	ADLARD,M ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	162.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.74	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.24	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.08 m³·mol⁻¹	ChemAxon
Polarizability	32.31 Å³	ChemAxon
Number of Rings	2	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]+	169.903	31661259
DarkChem	[M-H]-	171.488	31661259
DeepCCS	[M+H]+	164.07	30932474
DeepCCS	[M-H]-	161.674	30932474
DeepCCS	[M-2H]-	194.558	30932474
DeepCCS	[M+Na]+	170.11	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.6	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	170.6	32859911
AllCCS	[M+Na-2H]-	171.0	32859911
AllCCS	[M+HCOO]-	171.4	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.	4.22 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7157 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.18 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	120.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	536.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	82.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	251.1 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	270.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	857.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	667.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	66.6 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	1023.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	214.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	665.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	482.2 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	107.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sumatriptan	CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1	4184.5	Standard polar	33892256
Sumatriptan	CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1	2742.3	Standard non polar	33892256
Sumatriptan	CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1	2768.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sumatriptan,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C)C=C12	2664.5	Semi standard non polar	33892256
Sumatriptan,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C)C=C12	2646.5	Standard non polar	33892256
Sumatriptan,1TMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C)C=C12	3490.7	Standard polar	33892256
Sumatriptan,1TMS,isomer #2	CNS(=O)(=O)CC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C	2606.5	Semi standard non polar	33892256
Sumatriptan,1TMS,isomer #2	CNS(=O)(=O)CC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C	2627.0	Standard non polar	33892256
Sumatriptan,1TMS,isomer #2	CNS(=O)(=O)CC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C	3495.6	Standard polar	33892256
Sumatriptan,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C)C=C12	2657.9	Semi standard non polar	33892256
Sumatriptan,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C)C=C12	2783.2	Standard non polar	33892256
Sumatriptan,2TMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C)C=C12	3259.5	Standard polar	33892256
Sumatriptan,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C12	2880.8	Semi standard non polar	33892256
Sumatriptan,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C12	2910.9	Standard non polar	33892256
Sumatriptan,1TBDMS,isomer #1	CN(C)CCC1=C[NH]C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C12	3494.4	Standard polar	33892256
Sumatriptan,1TBDMS,isomer #2	CNS(=O)(=O)CC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C	2833.2	Semi standard non polar	33892256
Sumatriptan,1TBDMS,isomer #2	CNS(=O)(=O)CC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C	2851.9	Standard non polar	33892256
Sumatriptan,1TBDMS,isomer #2	CNS(=O)(=O)CC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C	3509.5	Standard polar	33892256
Sumatriptan,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C12	3088.8	Semi standard non polar	33892256
Sumatriptan,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C12	3259.7	Standard non polar	33892256
Sumatriptan,2TBDMS,isomer #1	CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C12	3334.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sumatriptan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-7390000000-5809ad2270f77ffcec79	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sumatriptan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9400000000-93cc7dc7e521f98aa292	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sumatriptan LC-ESI-qTof , Positive-QTOF	splash10-03di-0190000000-c12ee3ac5f29c3420996	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sumatriptan LC-ESI-qTof , Positive-QTOF	splash10-0a4i-2910000000-8769dc29dcac8fede7d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sumatriptan , positive-QTOF	splash10-0002-0390000000-cdddf05865e6d570c337	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sumatriptan , positive-QTOF	splash10-0a4i-2910000000-8769dc29dcac8fede7d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sumatriptan 35V, Negative-QTOF	splash10-001i-1090000000-b0360ed354c3c7a76195	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sumatriptan 35V, Positive-QTOF	splash10-0a4i-7970000000-4a9c99ffaf927876bb55	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 10V, Positive-QTOF	splash10-000t-0090000000-42a6041e68fbb33f3c3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 20V, Positive-QTOF	splash10-0uxr-1290000000-18f63d6714d369042ced	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 40V, Positive-QTOF	splash10-0a59-1910000000-b311f02f2295ff294573	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 10V, Negative-QTOF	splash10-0006-3090000000-23dacc0baf4eac1e818a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 20V, Negative-QTOF	splash10-00mo-9280000000-45a6f0dbb82744e4f102	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 40V, Negative-QTOF	splash10-01r6-9120000000-ca48d4e064a2f6323651	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 10V, Negative-QTOF	splash10-03dl-9000000000-a75e9a0167fac95c8ca3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 20V, Negative-QTOF	splash10-03dl-9530000000-af10011e851a42315cd8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 40V, Negative-QTOF	splash10-0a4l-2900000000-e271d3cf647593f64e67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 10V, Positive-QTOF	splash10-0002-0090000000-7a6d991d417845eb044c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 20V, Positive-QTOF	splash10-0zg4-2890000000-0b86cdf68f0a940df967	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sumatriptan 40V, Positive-QTOF	splash10-0006-9510000000-e92db5fc8036751fb26f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Brain

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00669

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023604

KNApSAcK ID

Not Available

Chemspider ID

5165

KEGG Compound ID

C07319

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sumatriptan

METLIN ID

2612

PubChem Compound

5358

PDB ID

Not Available

ChEBI ID

10650

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Torner Montoya, Miguel. Process for the synthesis of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide [sumatriptan]. Span. (1994), 6 pp. CODEN: SPXXAD ES 2059236 A1 19941101 CAN 122:265245 AN 1995:520544

Material Safety Data Sheet (MSDS)

Not Available

General References

Pascual J, del Arco C, Romon T, del Olmo E, Castro E, Pazos A: Autoradiographic distribution of [3H]sumatriptan-binding sites in post-mortem human brain. Cephalalgia. 1996 Aug;16(5):317-22. [PubMed:8869766 ]
Castro ME, Pascual J, Romon T, del Arco C, del Olmo E, Pazos A: Differential distribution of [3H]sumatriptan binding sites (5-HT1B, 5-HT1D and 5-HT1F receptors) in human brain: focus on brainstem and spinal cord. Neuropharmacology. 1997 Apr-May;36(4-5):535-42. [PubMed:9225278 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

2. Mitogen-activated protein kinase 1

General function:: Involved in MAP kinase activity
Specific function:: Acts as a transcriptional repressor. Binds to a [GC]AAA[GC] consensus sequence. Repress the expression of interferon gamma-induced genes. Seems to bind to the promoter of CCL5, DMP1, IFIH1, IFITM1, IRF7, IRF9, LAMP3, OAS1, OAS2, OAS3 and STAT1. Transcriptional activity is independent of kinase activity
Gene Name:: MAPK1
Uniprot ID:: P28482
Molecular weight:: 41389.3

Enzyme Details

3. Mitogen-activated protein kinase 3

General function:: Involved in MAP kinase activity
Specific function:: Involved in both the initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors such as ELK-1. Phosphorylates EIF4EBP1; required for initiation of translation. Phosphorylates microtubule-associated protein 2 (MAP2). Phosphorylates SPZ1. Phosphorylates heat shock factor protein 4 (HSF4)
Gene Name:: MAPK3
Uniprot ID:: P27361
Molecular weight:: 43135.2

Enzyme Details

4. Inhibitor of nuclear factor kappa-B kinase subunit beta

General function:: Involved in protein kinase activity
Specific function:: Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. Also phosphorylates NCOA3
Gene Name:: IKBKB
Uniprot ID:: O14920
Molecular weight:: 86563.2

Enzyme Details

5. RAC-alpha serine/threonine-protein kinase

General function:: Involved in protein serine/threonine kinase activity
Specific function:: Plays a role as a key modulator of the AKT-mTOR signaling pathway controlling the tempo of the process of newborn neurons integration during adult neurogenesis, including correct neuron positioning, dendritic development and synapse formation. General protein kinase capable of phosphorylating several known proteins. Phosphorylates TBC1D4. Signals downstream of phosphatidylinositol 3-kinase (PI(3)K) to mediate the effects of various growth factors such as platelet-derived growth factor (PDGF), epidermal growth factor (EGF), insulin and insulin-like growth factor I (IGF-I). Plays a role in glucose transport by mediating insulin-induced translocation of the GLUT4 glucose transporter to the cell surface. Mediates the antiapoptotic effects of IGF-I. Mediates insulin-stimulated protein synthesis by phosphorylating TSC2 at 'Ser-939' and 'Thr-1462', thereby activating mTORC1 signaling and leading to both phosphorylation of 4E-BP1 and in activation of RPS6KB1. Promotes glycogen synthesis by mediating the insulin-induced activation of glycogen synthase
Gene Name:: AKT1
Uniprot ID:: P31749
Molecular weight:: 55686.0

Enzyme Details

6. BR serine/threonine-protein kinase 1

General function:: Involved in protein kinase activity
Specific function:: Required for the polarization of forebrain neurons which endows axons and dendrites with distinct properties, possibly by locally regulating phosphorylation of microtubule-associated proteins. May be involved in the regulation of G2/M arrest in response to UV- or methyl methane sulfonate (MMS)- induced, but not IR-induced, DNA damage. Phosphorylates WEE1 and CDC25B in vitro and CDC25C in vitro and in vivo
Gene Name:: BRSK1
Uniprot ID:: Q8TDC3
Molecular weight:: 86752.7

Enzyme Details

7. 5-hydroxytryptamine receptor 2B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2B
Uniprot ID:: P41595
Molecular weight:: 54297.4

Enzyme Details

8. 5-hydroxytryptamine receptor 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

Enzyme Details

9. 5-hydroxytryptamine receptor 1F

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1F
Uniprot ID:: P30939
Molecular weight:: 41708.5

Enzyme Details

10. 5-hydroxytryptamine receptor 1D

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1D
Uniprot ID:: P28221
Molecular weight:: 41906.4

Showing metabocard for Sumatriptan (HMDB0005037)

MOL for HMDB0005037 (Sumatriptan)

3D MOL for HMDB0005037 (Sumatriptan)

3D SDF for HMDB0005037 (Sumatriptan)

3D-SDF for HMDB0005037 (Sumatriptan)

PDB for HMDB0005037 (Sumatriptan)

3D PDB for HMDB0005037 (Sumatriptan)

SMILES for HMDB0005037 (Sumatriptan)

INCHI for HMDB0005037 (Sumatriptan)

Structure for HMDB0005037 (Sumatriptan)

3D Structure for HMDB0005037 (Sumatriptan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes