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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015104

Secondary Accession Numbers

HMDB15104

Metabolite Identification

Common Name

Alosetron

Description

Alosetron is a 5-HT3 antagonist used only for the management of severe diarrhoea-predominant irritable bowel syndrome (IBS) in women. Alosetron has an antagonist action on the 5-HT3 receptors and thus may modulate serotonin-sensitive gastrointestinal (GI) processes. Alosetron was voluntarily withdrawn from the US market in November 2000 by the manufacturer due to numerous reports of severe adverse effects including ischemic colitis, severely obstructed or ruptured bowel, and death. In June 2002, the FDA approved a supplemental new drug application allowing the remarketing of the drug under restricted conditions of use.

Structure

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

HMDB0015104
     RDKit          3D
Alosetron
 40 43  0  0  0  0  0  0  0  0999 V2000
   -5.3230   -1.3016    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594   -0.1531   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2785    0.9528   -0.5627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3617    1.7971   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    1.2030   -0.9289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.0057   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.9641    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.4959   -0.3584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827   -0.7786   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -1.4056   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206   -0.6140   -0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    0.1926    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    0.8031    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595    1.6720    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.1232    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6629    1.7001    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710    0.8244    0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4694    0.3638    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -0.4748   -0.5145 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463   -1.1296   -1.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661    0.2735    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    0.9753    1.4246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686   -0.9296    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -2.0533    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017   -1.7748   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3033    1.1746   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221    2.7662   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -1.9500   -0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -1.2254    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354    0.2115   -2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575   -1.4057   -2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095   -2.4668   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -1.3781   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3619    2.0334    2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484    2.8033    3.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    2.0564    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5922    0.4795    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -2.1509   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999   -0.5599   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -1.1995   -2.4178 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  6  2  2  0
 21  8  1  0
 19 11  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

969
  Mrv0541 02231215082D          

 22 25  0  0  0  0            999 V2000
    4.2709   -1.6687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327   -0.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859    0.9221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2223   -1.7142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7481   -0.5454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2266    0.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309    0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5876    0.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899   -0.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450    0.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243   -0.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8604   -1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859    1.7142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6473   -0.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6357   -1.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8391   -0.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841    0.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9607   -0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5673    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9098   -1.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0  0  0  0
  2  9  1  0  0  0  0
  2 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3  6  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  4 17  1  0  0  0  0
  4 22  2  0  0  0  0
  5 20  1  0  0  0  0
  5 22  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 16  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 19  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015104

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)

> <INCHI_KEY>
JSWZEAMFRNKZNL-UHFFFAOYSA-N

> <FORMULA>
C17H18N4O

> <MOLECULAR_WEIGHT>
294.351

> <EXACT_MASS>
294.148061218

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.51709086196463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-1-one

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
1.2119007720000001

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.315838762552861

> <JCHEM_PKA_STRONGEST_BASIC>
6.809476550701925

> <JCHEM_POLAR_SURFACE_AREA>
53.92

> <JCHEM_REFRACTIVITY>
86.40540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alosetron

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015104
     RDKit          3D
Alosetron
 40 43  0  0  0  0  0  0  0  0999 V2000
   -5.3230   -1.3016    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594   -0.1531   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2785    0.9528   -0.5627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3617    1.7971   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    1.2030   -0.9289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.0057   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.9641    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.4959   -0.3584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827   -0.7786   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -1.4056   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206   -0.6140   -0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    0.1926    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    0.8031    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595    1.6720    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.1232    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6629    1.7001    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710    0.8244    0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4694    0.3638    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -0.4748   -0.5145 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463   -1.1296   -1.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661    0.2735    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    0.9753    1.4246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686   -0.9296    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -2.0533    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017   -1.7748   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3033    1.1746   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221    2.7662   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -1.9500   -0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -1.2254    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354    0.2115   -2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575   -1.4057   -2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095   -2.4668   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -1.3781   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3619    2.0334    2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484    2.8033    3.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    2.0564    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5922    0.4795    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -2.1509   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999   -0.5599   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -1.1995   -2.4178 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  6  2  2  0
 21  8  1  0
 19 11  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 969                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.972  -3.115   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       9.954  -1.406   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       6.694   1.721   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      13.482  -3.200   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      14.463  -1.018   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.890   0.852   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.391   1.196   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.433  -0.554   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.430   0.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954  -0.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.497   0.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.445  -1.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.939  -2.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.694   3.200   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.942  -1.714   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.996   1.196   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.387  -2.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.433  -1.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.957   0.059   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.993  -0.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.259   0.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.765  -2.466   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2    9   12   13                                                  
CONECT    3    6   11   14                                                  
CONECT    4   17   22                                                       
CONECT    5   20   22                                                       
CONECT    6    3    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10   12                                                  
CONECT    9    2    7                                                       
CONECT   10    8   11   15                                                  
CONECT   11    3   10   16                                                  
CONECT   12    1    2    8                                                  
CONECT   13    2   17                                                       
CONECT   14    3                                                            
CONECT   15   10   18                                                       
CONECT   16   11   19                                                       
CONECT   17    4   13   20                                                  
CONECT   18   15   19                                                       
CONECT   19   16   18                                                       
CONECT   20    5   17   21                                                  
CONECT   21   20                                                            
CONECT   22    4    5                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0015104
HETATM    1  C1  UNL     1      -5.323  -1.302   0.538  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.659  -0.153  -0.097  1.00  0.00           C  
HETATM    3  N1  UNL     1      -5.278   0.953  -0.563  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.362   1.797  -1.079  1.00  0.00           C  
HETATM    5  N2  UNL     1      -3.165   1.203  -0.929  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.310   0.006  -0.330  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.271  -0.964   0.021  1.00  0.00           C  
HETATM    8  N3  UNL     1      -0.957  -0.496  -0.358  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.383  -0.779  -1.660  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.974  -1.406  -1.545  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.821  -0.614  -0.623  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.281   0.193   0.383  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.293   0.803   1.080  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.259   1.672   2.139  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.465   2.123   2.633  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.663   1.700   2.064  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.671   0.824   0.998  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.469   0.364   0.492  1.00  0.00           C  
HETATM   19  N4  UNL     1       3.166  -0.475  -0.514  1.00  0.00           N  
HETATM   20  C16 UNL     1       4.146  -1.130  -1.356  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.166   0.273   0.545  1.00  0.00           C  
HETATM   22  O1  UNL     1      -0.725   0.975   1.425  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.869  -0.930   1.431  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.583  -2.053   0.865  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.002  -1.775  -0.196  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.303   1.175  -0.552  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.522   2.766  -1.532  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.441  -1.950  -0.496  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.302  -1.225   1.116  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.235   0.212  -2.173  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.057  -1.406  -2.280  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.910  -2.467  -1.202  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.469  -1.378  -2.537  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.362   2.033   2.620  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.548   2.803   3.457  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.630   2.056   2.454  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.592   0.480   0.537  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.309  -2.151  -0.952  1.00  0.00           H  
HETATM   39  H17 UNL     1       5.100  -0.560  -1.407  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.786  -1.200  -2.418  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    6    6
CONECT    3    4   26
CONECT    4    5    5   27
CONECT    5    6
CONECT    6    7
CONECT    7    8   28   29
CONECT    8    9   21
CONECT    9   10   30   31
CONECT   10   11   32   33
CONECT   11   12   12   19
CONECT   12   13   21
CONECT   13   14   14   18
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19
CONECT   19   20
CONECT   20   38   39   40
CONECT   21   22   22
END

HMDB0015104
     RDKit          3D
Alosetron
 40 43  0  0  0  0  0  0  0  0999 V2000
   -5.3230   -1.3016    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6594   -0.1531   -0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2785    0.9528   -0.5627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3617    1.7971   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652    1.2030   -0.9289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3103    0.0057   -0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.9641    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574   -0.4959   -0.3584 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827   -0.7786   -1.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741   -1.4056   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8206   -0.6140   -0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815    0.1926    0.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    0.8031    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595    1.6720    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.1232    2.6333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6629    1.7001    2.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710    0.8244    0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4694    0.3638    0.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663   -0.4748   -0.5145 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1463   -1.1296   -1.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661    0.2735    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    0.9753    1.4246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8686   -0.9296    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -2.0533    0.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0017   -1.7748   -0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3033    1.1746   -0.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221    2.7662   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -1.9500   -0.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -1.2254    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354    0.2115   -2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575   -1.4057   -2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9095   -2.4668   -1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -1.3781   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3619    2.0334    2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484    2.8033    3.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6297    2.0564    2.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5922    0.4795    0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3086   -2.1509   -0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999   -0.5599   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7863   -1.1995   -2.4178 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
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  6  2  2  0
 21  8  1  0
 19 11  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one	ChEBI
Alosetron HCL	HMDB
Alosetron monohydrochloride	HMDB
Lotronex	HMDB
Alosetron hydrochloride	HMDB
2,3,4,5-Tetrahydro-5-methyl-2-((5-methylimidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one monohydrochloride	HMDB
GlaxoSmithKline brand OF alosetron hydrochloride	HMDB

Chemical Formula

C₁₇H₁₈N₄O

Average Molecular Weight

294.351

Monoisotopic Molecular Weight

294.148061218

IUPAC Name

5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-1-one

Traditional Name

alosetron

CAS Registry Number

122852-42-0

SMILES

CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2

InChI Identifier

InChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)

InChI Key

JSWZEAMFRNKZNL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

N-alkylindoles

Direct Parent

N-alkylindoles

Alternative Parents

Substituents

N-alkylindole
Indole
N-methylpyrrole
Substituted pyrrole
Benzenoid
Imidazole
Heteroaromatic compound
Pyrrole
Vinylogous amide
Azole
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoles (CHEBI:253342 )
pyridoindole (CHEBI:253342 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015104)

Source

Exogenous

Exogenous (HMDB: HMDB0015104)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.44 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	1.85	ALOGPS
logP	1.21	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.32	ChemAxon
pKa (Strongest Basic)	6.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.41 m³·mol⁻¹	ChemAxon
Polarizability	32.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.108	31661259
DarkChem	[M-H]-	167.395	31661259
DeepCCS	[M-2H]-	197.726	30932474
DeepCCS	[M+Na]+	173.213	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	172.8	32859911
AllCCS	[M+Na]+	173.8	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.6	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.	5.75 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2776 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1159.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	136.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	329.8 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	320.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	617.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	711.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	339.5 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	1103.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	241.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	243.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	363.1 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	95.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alosetron	CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2	3928.6	Standard polar	33892256
Alosetron	CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2	2905.9	Standard non polar	33892256
Alosetron	CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2	3239.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alosetron,1TMS,isomer #1	CC1=C(CN2CCC3=C(C2=O)C2=CC=CC=C2N3C)N=CN1[Si](C)(C)C	2934.9	Semi standard non polar	33892256
Alosetron,1TMS,isomer #1	CC1=C(CN2CCC3=C(C2=O)C2=CC=CC=C2N3C)N=CN1[Si](C)(C)C	2796.3	Standard non polar	33892256
Alosetron,1TMS,isomer #1	CC1=C(CN2CCC3=C(C2=O)C2=CC=CC=C2N3C)N=CN1[Si](C)(C)C	3550.8	Standard polar	33892256
Alosetron,1TBDMS,isomer #1	CC1=C(CN2CCC3=C(C2=O)C2=CC=CC=C2N3C)N=CN1[Si](C)(C)C(C)(C)C	3182.1	Semi standard non polar	33892256
Alosetron,1TBDMS,isomer #1	CC1=C(CN2CCC3=C(C2=O)C2=CC=CC=C2N3C)N=CN1[Si](C)(C)C(C)(C)C	2990.6	Standard non polar	33892256
Alosetron,1TBDMS,isomer #1	CC1=C(CN2CCC3=C(C2=O)C2=CC=CC=C2N3C)N=CN1[Si](C)(C)C(C)(C)C	3611.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alosetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-054p-9640000000-36ec950b2b5a4de0d766	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alosetron 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alosetron , positive-QTOF	splash10-0udi-0390000000-3b813a9458d2bce7516f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alosetron 35V, Positive-QTOF	splash10-0udi-3390000000-9994f53a2714bf016b00	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 10V, Positive-QTOF	splash10-0002-5090000000-aa22d1e533a9ade9a631	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 20V, Positive-QTOF	splash10-0002-9470000000-de378c4e797603ddebd5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 40V, Positive-QTOF	splash10-0udj-9000000000-4320dc79a39aa798ebed	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 10V, Negative-QTOF	splash10-0006-0090000000-61b91fd4d7827b2dee3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 20V, Negative-QTOF	splash10-0006-1690000000-1c0db2dce26ffd0716f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 40V, Negative-QTOF	splash10-001i-4900000000-bac7a8e86a49765da618	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 10V, Positive-QTOF	splash10-0002-0090000000-0a33faab2e775c338d55	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 20V, Positive-QTOF	splash10-0002-0090000000-6aa9a0fa5a9c1aeeb778	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 40V, Positive-QTOF	splash10-001i-9320000000-27c420ad3c1a98b56add	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 10V, Negative-QTOF	splash10-0006-0090000000-abdd2e02132168abe3fa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 20V, Negative-QTOF	splash10-0006-0190000000-c8bf656d3129fa7c6a2c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alosetron 40V, Negative-QTOF	splash10-03di-0290000000-dacd12d29c5302eb8887	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00969	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00969	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00969

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alosetron

METLIN ID

Not Available

PubChem Compound

2099

PDB ID

Not Available

ChEBI ID

253342

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

Mayer EA, Bradesi S: Alosetron and irritable bowel syndrome. Expert Opin Pharmacother. 2003 Nov;4(11):2089-98. [PubMed:14596662 ]
Camilleri M: Pharmacology and clinical experience with alosetron. Expert Opin Investig Drugs. 2000 Jan;9(1):147-59. [PubMed:11060667 ]
Rahimi R, Nikfar S, Abdollahi M: Efficacy and tolerability of alosetron for the treatment of irritable bowel syndrome in women and men: a meta-analysis of eight randomized, placebo-controlled, 12-week trials. Clin Ther. 2008 May;30(5):884-901. doi: 10.1016/j.clinthera.2008.05.002. [PubMed:18555935 ]
Lewis JH: Alosetron for severe diarrhea-predominant irritable bowel syndrome: safety and efficacy in perspective. Expert Rev Gastroenterol Hepatol. 2010 Feb;4(1):13-29. doi: 10.1586/egh.09.72. [PubMed:20136586 ]
Andresen V, Hollerbach S: Reassessing the benefits and risks of alosetron: what is its place in the treatment of irritable bowel syndrome? Drug Saf. 2004;27(5):283-92. [PubMed:15061683 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. 5-hydroxytryptamine receptor 3A

General function:: Involved in extracellular ligand-gated ion channel activity
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 is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:: HTR3A
Uniprot ID:: P46098
Molecular weight:: 55279.8

References

Clayton NM, Sargent R, Butler A, Gale J, Maxwell MP, Hunt AA, Barrett VJ, Cambridge D, Bountra C, Humphrey PP: The pharmacological properties of the novel selective 5-HT3 receptor antagonist, alosetron, and its effects on normal and perturbed small intestinal transit in the fasted rat. Neurogastroenterol Motil. 1999 Jun;11(3):207-17. [PubMed:10354345 ]
Mayer EA, Bradesi S: Alosetron and irritable bowel syndrome. Expert Opin Pharmacother. 2003 Nov;4(11):2089-98. [PubMed:14596662 ]
Coldwell JR, Phillis BD, Sutherland K, Howarth GS, Blackshaw LA: Increased responsiveness of rat colonic splanchnic afferents to 5-HT after inflammation and recovery. J Physiol. 2007 Feb 15;579(Pt 1):203-13. Epub 2006 Nov 30. [PubMed:17138606 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Houghton LA, Foster JM, Whorwell PJ: Alosetron, a 5-HT3 receptor antagonist, delays colonic transit in patients with irritable bowel syndrome and healthy volunteers. Aliment Pharmacol Ther. 2000 Jun;14(6):775-82. [PubMed:10848662 ]
Gunput MD: Review article: clinical pharmacology of alosetron. Aliment Pharmacol Ther. 1999 May;13 Suppl 2:70-6. [PubMed:10429744 ]
Balfour JA, Goa KL, Perry CM: Alosetron. Drugs. 2000 Mar;59(3):511-8; discussion 519-20. [PubMed:10776833 ]
Camilleri M: Pharmacology and clinical experience with alosetron. Expert Opin Investig Drugs. 2000 Jan;9(1):147-59. [PubMed:11060667 ]
Rahimi R, Nikfar S, Abdollahi M: Efficacy and tolerability of alosetron for the treatment of irritable bowel syndrome in women and men: a meta-analysis of eight randomized, placebo-controlled, 12-week trials. Clin Ther. 2008 May;30(5):884-901. doi: 10.1016/j.clinthera.2008.05.002. [PubMed:18555935 ]
Lewis JH: Alosetron for severe diarrhea-predominant irritable bowel syndrome: safety and efficacy in perspective. Expert Rev Gastroenterol Hepatol. 2010 Feb;4(1):13-29. doi: 10.1586/egh.09.72. [PubMed:20136586 ]
Andresen V, Hollerbach S: Reassessing the benefits and risks of alosetron: what is its place in the treatment of irritable bowel syndrome? Drug Saf. 2004;27(5):283-92. [PubMed:15061683 ]

Showing metabocard for Alosetron (HMDB0015104)

MOL for HMDB0015104 (Alosetron)

3D MOL for HMDB0015104 (Alosetron)

3D SDF for HMDB0015104 (Alosetron)

3D-SDF for HMDB0015104 (Alosetron)

PDB for HMDB0015104 (Alosetron)

3D PDB for HMDB0015104 (Alosetron)

SMILES for HMDB0015104 (Alosetron)

INCHI for HMDB0015104 (Alosetron)

Structure for HMDB0015104 (Alosetron)

3D Structure for HMDB0015104 (Alosetron)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References