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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-22 19:51:19 UTC

Update Date

2021-09-14 15:02:27 UTC

HMDB ID

HMDB0061153

Secondary Accession Numbers

HMDB61153

Metabolite Identification

Common Name

Lorcaserin sulfamate

Description

Lorcaserin sulfamate is a metabolite of lorcaserin. Lorcaserin (APD-356, trade name Lorqess) is a weight-loss drug developed by Arena Pharmaceuticals. It has serotonergic properties and acts as an anorectic. On 22 December 2009 a New Drug Application (NDA) was submitted to the Food and Drug Administration (FDA) in the United States. On 16 September 2010, an FDA advisory panel voted to recommend against approval of the drug based on concerns over both safety and efficacy. (Wikipedia)

Structure

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

HMDB0061153
     RDKit          3D
Lorcaserin sulfamate
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.5178   -2.5450   -1.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -1.1010   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256   -0.8054    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066    0.5302    0.9688 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    0.8588    2.3580 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5485    2.2022    2.9141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7180   -0.2345    3.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5350    0.8115    1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573    1.5473    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1185    1.9995   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053    0.8584   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    1.2932   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343    0.3681   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -0.9871   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5219   -2.1072   -0.4381 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804   -1.4435   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561   -0.5213   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -2.8716   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420   -2.8189   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -3.1513   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273   -0.5390   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.5691    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -0.7865    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.6782    2.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    1.1452   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628    2.4476    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    2.2565   -1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238    2.8457   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    2.3680   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4415    0.7688   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410   -2.4978   -0.6416 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  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  4  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
 14 16  1  0
 16 17  2  0
 17  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
M  END

  Mrv0541 07221312512D          

 17 18  0  0  0  0            999 V2000
   -2.3277    2.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421    1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    1.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132    1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987    2.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843    1.6205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7566    1.2080    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6407    1.6205    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6407    0.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6407    2.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657    1.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0093    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4218    0.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16  5  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061153

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CN(CCC2=C1C=C(Cl)C=C2)S(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14ClNO3S/c1-8-7-13(17(14,15)16)5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8H,4-5,7H2,1H3,(H,14,15,16)

> <INCHI_KEY>
YZUNJIOOIHWHGQ-UHFFFAOYSA-N

> <FORMULA>
C11H14ClNO3S

> <MOLECULAR_WEIGHT>
275.752

> <EXACT_MASS>
275.038291716

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.005770617979042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine-3-sulfonic acid

> <ALOGPS_LOGP>
0.23

> <JCHEM_LOGP>
2.0529644923333334

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3148776937124884

> <JCHEM_PKA_STRONGEST_BASIC>
-9.93492750322984

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
67.0532

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-chloro-1-methyl-1,2,4,5-tetrahydro-3-benzazepine-3-sulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061153
     RDKit          3D
Lorcaserin sulfamate
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.5178   -2.5450   -1.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -1.1010   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256   -0.8054    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066    0.5302    0.9688 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    0.8588    2.3580 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5485    2.2022    2.9141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7180   -0.2345    3.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5350    0.8115    1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573    1.5473    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1185    1.9995   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053    0.8584   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    1.2932   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343    0.3681   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -0.9871   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5219   -2.1072   -0.4381 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804   -1.4435   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561   -0.5213   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -2.8716   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420   -2.8189   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -3.1513   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273   -0.5390   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.5691    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -0.7865    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.6782    2.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    1.1452   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628    2.4476    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    2.2565   -1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238    2.8457   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    2.3680   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4415    0.7688   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410   -2.4978   -0.6416 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  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  4  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
 14 16  1  0
 16 17  2  0
 17  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 22-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUL-13         0                                  
HETATM    1  C   UNK     0      -4.345   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.679   4.565   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.679   3.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.345   2.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.011   3.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.011   4.565   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.678   5.335   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.344   3.025   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.344   4.565   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -7.012   2.255   0.000  0.00  0.00          Cl+0
HETATM   11  S   UNK     0       1.196   3.025   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       1.196   1.485   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.196   4.565   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.736   3.025   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.344   1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.884   1.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.654   0.151   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6    9                                                       
CONECT    8    9   11   15                                                  
CONECT    9    8    7                                                       
CONECT   10    3                                                            
CONECT   11    8   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    8   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0061153
HETATM    1  C1  UNL     1       0.518  -2.545  -1.162  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.484  -1.101  -0.780  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.226  -0.805   0.500  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.907   0.530   0.969  1.00  0.00           N  
HETATM    5  S1  UNL     1       1.910   0.859   2.358  1.00  0.00           S  
HETATM    6  O1  UNL     1       1.549   2.202   2.914  1.00  0.00           O  
HETATM    7  O2  UNL     1       1.718  -0.235   3.393  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.535   0.812   1.923  1.00  0.00           O  
HETATM    9  C4  UNL     1       1.157   1.547   0.004  1.00  0.00           C  
HETATM   10  C5  UNL     1      -0.119   1.999  -0.711  1.00  0.00           C  
HETATM   11  C6  UNL     1      -1.105   0.858  -0.653  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.411   1.293  -0.558  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.434   0.368  -0.494  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.179  -0.987  -0.523  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -4.522  -2.107  -0.438  1.00  0.00          CL  
HETATM   16  C10 UNL     1      -1.880  -1.443  -0.617  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.856  -0.521  -0.681  1.00  0.00           C  
HETATM   18  H1  UNL     1       1.541  -2.872  -1.444  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.142  -2.819  -1.979  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.254  -3.151  -0.253  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.027  -0.539  -1.586  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.110  -1.569   1.264  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.321  -0.787   0.238  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.973   1.678   2.144  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.840   1.145  -0.772  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.663   2.448   0.428  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.127   2.257  -1.746  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.524   2.846  -0.137  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.604   2.368  -0.536  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.442   0.769  -0.421  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.641  -2.498  -0.642  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   17   21
CONECT    3    4   22   23
CONECT    4    5    9
CONECT    5    6    6    7    7
CONECT    5    8
CONECT    8   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   16   17   17   31
END

HMDB0061153
     RDKit          3D
Lorcaserin sulfamate
 31 32  0  0  0  0  0  0  0  0999 V2000
    0.5178   -2.5450   -1.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4841   -1.1010   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2256   -0.8054    0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066    0.5302    0.9688 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    0.8588    2.3580 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5485    2.2022    2.9141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7180   -0.2345    3.3933 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5350    0.8115    1.9229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573    1.5473    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1185    1.9995   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053    0.8584   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4108    1.2932   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4343    0.3681   -0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1786   -0.9871   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5219   -2.1072   -0.4381 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8804   -1.4435   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561   -0.5213   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5408   -2.8716   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420   -2.8189   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -3.1513   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273   -0.5390   -1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1097   -1.5691    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209   -0.7865    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9732    1.6782    2.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    1.1452   -0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628    2.4476    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    2.2565   -1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238    2.8457   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    2.3680   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4415    0.7688   -0.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6410   -2.4978   -0.6416 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  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  4  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
 14 16  1  0
 16 17  2  0
 17  2  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lorcaserin sulfamic acid	Generator
Lorcaserin sulphamate	Generator
Lorcaserin sulphamic acid	Generator

Chemical Formula

C₁₁H₁₄ClNO₃S

Average Molecular Weight

275.752

Monoisotopic Molecular Weight

275.038291716

IUPAC Name

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine-3-sulfonic acid

Traditional Name

8-chloro-1-methyl-1,2,4,5-tetrahydro-3-benzazepine-3-sulfonic acid

CAS Registry Number

Not Available

SMILES

CC1CN(CCC2=C1C=C(Cl)C=C2)S(O)(=O)=O

InChI Identifier

InChI=1S/C11H14ClNO3S/c1-8-7-13(17(14,15)16)5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8H,4-5,7H2,1H3,(H,14,15,16)

InChI Key

YZUNJIOOIHWHGQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Azepine
Aryl chloride
Aryl halide
Sulfuric acid monoamide
Benzenoid
Organic sulfuric acid or derivatives
Azacycle
Organic nitrogen compound
Organochloride
Organonitrogen compound
Hydrocarbon derivative
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061153)

Organ

Liver (HMDB: HMDB0061153)
Kidney (HMDB: HMDB0061153)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061153)

Cellular substructure

Cytoplasm (HMDB: HMDB0061153)
Membrane (HMDB: HMDB0061153)

Source

Endogenous

Endogenous (HMDB: HMDB0061153)

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	0.046 g/L	ALOGPS
logP	0.23	ALOGPS
logP	2.05	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	-9.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.05 m³·mol⁻¹	ChemAxon
Polarizability	27.01 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
DeepCCS	[M+H]+	155.271	30932474
DeepCCS	[M-H]-	152.913	30932474
DeepCCS	[M-2H]-	185.799	30932474
DeepCCS	[M+Na]+	161.364	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	155.1	32859911
AllCCS	[M+NH4]+	162.2	32859911
AllCCS	[M+Na]+	163.1	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	157.5	32859911
AllCCS	[M+HCOO]-	157.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lorcaserin sulfamate	CC1CN(CCC2=C1C=C(Cl)C=C2)S(O)(=O)=O	3303.7	Standard polar	33892256
Lorcaserin sulfamate	CC1CN(CCC2=C1C=C(Cl)C=C2)S(O)(=O)=O	2202.4	Standard non polar	33892256
Lorcaserin sulfamate	CC1CN(CCC2=C1C=C(Cl)C=C2)S(O)(=O)=O	2314.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lorcaserin sulfamate,1TMS,isomer #1	CC1CN(S(=O)(=O)O[Si](C)(C)C)CCC2=CC=C(Cl)C=C21	2271.6	Semi standard non polar	33892256
Lorcaserin sulfamate,1TMS,isomer #1	CC1CN(S(=O)(=O)O[Si](C)(C)C)CCC2=CC=C(Cl)C=C21	2318.9	Standard non polar	33892256
Lorcaserin sulfamate,1TMS,isomer #1	CC1CN(S(=O)(=O)O[Si](C)(C)C)CCC2=CC=C(Cl)C=C21	3123.6	Standard polar	33892256
Lorcaserin sulfamate,1TBDMS,isomer #1	CC1CN(S(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C21	2488.4	Semi standard non polar	33892256
Lorcaserin sulfamate,1TBDMS,isomer #1	CC1CN(S(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C21	2642.0	Standard non polar	33892256
Lorcaserin sulfamate,1TBDMS,isomer #1	CC1CN(S(=O)(=O)O[Si](C)(C)C(C)(C)C)CCC2=CC=C(Cl)C=C21	3203.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lorcaserin sulfamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr6-0930000000-665399af058b1adef847	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lorcaserin sulfamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lorcaserin sulfamate 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 - Lorcaserin sulfamate 10V, Positive-QTOF	splash10-004i-0490000000-d45fc9db665cbd01e7d2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 20V, Positive-QTOF	splash10-052g-0890000000-097132f44799f6a51b97	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 40V, Positive-QTOF	splash10-0uxr-1900000000-14dd1babde80ee8c96d1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 10V, Negative-QTOF	splash10-00di-3090000000-97343f8dc3b6fce72d0b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 20V, Negative-QTOF	splash10-00e9-5390000000-50d7b8f67af9d003f403	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 40V, Negative-QTOF	splash10-001i-9200000000-4d9897202cc623fa4d67	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 10V, Positive-QTOF	splash10-004i-0390000000-19e5ad4d30829b44a96a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 20V, Positive-QTOF	splash10-01r2-0910000000-e20820b9574486796655	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 40V, Positive-QTOF	splash10-0006-1900000000-6cb3efcf871d2bf07ed1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 10V, Negative-QTOF	splash10-00di-1090000000-3ecef9bf3b55a34c670f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 20V, Negative-QTOF	splash10-001i-9330000000-1202c3e338b7a22ae103	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lorcaserin sulfamate 40V, Negative-QTOF	splash10-001i-9010000000-1b2f9c1a5ddd632698cd	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

131770054

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 Lorcaserin sulfamate (HMDB0061153)

MOL for HMDB0061153 (Lorcaserin sulfamate)

3D MOL for HMDB0061153 (Lorcaserin sulfamate)

3D SDF for HMDB0061153 (Lorcaserin sulfamate)

3D-SDF for HMDB0061153 (Lorcaserin sulfamate)

PDB for HMDB0061153 (Lorcaserin sulfamate)

3D PDB for HMDB0061153 (Lorcaserin sulfamate)

SMILES for HMDB0061153 (Lorcaserin sulfamate)

INCHI for HMDB0061153 (Lorcaserin sulfamate)

Structure for HMDB0061153 (Lorcaserin sulfamate)

3D Structure for HMDB0061153 (Lorcaserin sulfamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra