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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:58 UTC

Update Date

2019-07-23 07:15:33 UTC

HMDB ID

HMDB0061003

Secondary Accession Numbers

HMDB61003

Metabolite Identification

Common Name

lansoprazole sulfide

Description

lansoprazole sulfide is a metabolite of lansoprazole. Lansoprazole is a proton-pump inhibitor (PPI) which inhibits the stomach's production of gastric acids. It is manufactured by a number of companies worldwide under several brand names. In the United States it was first approved by the Food and Drug Administration (FDA) in 1995. Lansoprazole has been available as a generic drug since Prevacid patent protection expired on November 10, 2009. Since 2009 Lansoprazole has been available over the counter (OTC) in the U.S. (Wikipedia)

Structure

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

HMDB0061003
     RDKit          3D
lansoprazole sulfide
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.5046   -0.5017   -2.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935    0.9378   -1.8213 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448    0.4745   -0.2020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.0370    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.2570    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.8993    2.2336 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243   -1.2236    2.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.9078    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.2640    0.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6365    0.0522   -0.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9609   -0.2397    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664    0.2822   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792    0.0358   -0.5205 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291   -0.2866   -1.9664 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336    1.6524   -0.8941 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2398    0.0597    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867    0.8858   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632   -0.2922    1.8036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -0.0511    1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6391   -0.2022    2.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    0.1445    1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490    0.6340    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4233    0.7888   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    0.4352    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -1.1396   -2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -1.1512   -2.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -0.1505   -4.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -1.7393    3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -1.1703    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -1.3327    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586    0.3324    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    1.7685   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    0.3734   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    1.4023   -0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -0.5958    3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7600    0.0263    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5476    0.9048   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3443    1.1772   -1.5720 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  9 16  2  0
 16 17  1  0
  4 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 16  5  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
M  END


  Mrv0541 07091309112D          

 24 26  0  0  0  0            999 V2000
   -0.1712    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    1.5229    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7732    0.3960    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442    1.2210    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 10  1  1  0  0  0  0
 11  5  2  0  0  0  0
 12  6  2  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 16  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  2  0  0  0  0
 21 11  1  0  0  0  0
 21 15  2  0  0  0  0
 22 12  1  0  0  0  0
 22 15  1  0  0  0  0
 23  9  1  0  0  0  0
 23 13  1  0  0  0  0
 24  2  1  0  0  0  0
 24 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061003

> <DATABASE_NAME>
hmdb

> <SMILES>
CSN1C2=CC=CC=C2N=C1C1=NC=CC(OCC(F)(F)F)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C16H14F3N3OS/c1-10-13(23-9-16(17,18)19)7-8-20-14(10)15-21-11-5-3-4-6-12(11)22(15)24-2/h3-8H,9H2,1-2H3

> <INCHI_KEY>
RZSYMONMXLYBMJ-UHFFFAOYSA-N

> <FORMULA>
C16H14F3N3OS

> <MOLECULAR_WEIGHT>
353.362

> <EXACT_MASS>
353.08096739

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.35598277297338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1-(methylsulfanyl)-1H-1,3-benzodiazole

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.989722502666667

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.858465430474833

> <JCHEM_PKA_STRONGEST_BASIC>
2.751929291122802

> <JCHEM_POLAR_SURFACE_AREA>
39.94

> <JCHEM_REFRACTIVITY>
98.68000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1-(methylsulfanyl)-1,3-benzodiazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061003
     RDKit          3D
lansoprazole sulfide
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.5046   -0.5017   -2.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935    0.9378   -1.8213 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448    0.4745   -0.2020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.0370    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.2570    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.8993    2.2336 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243   -1.2236    2.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.9078    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.2640    0.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6365    0.0522   -0.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9609   -0.2397    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664    0.2822   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792    0.0358   -0.5205 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291   -0.2866   -1.9664 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336    1.6524   -0.8941 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2398    0.0597    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867    0.8858   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632   -0.2922    1.8036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -0.0511    1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6391   -0.2022    2.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    0.1445    1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490    0.6340    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4233    0.7888   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    0.4352    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -1.1396   -2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -1.1512   -2.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -0.1505   -4.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -1.7393    3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -1.1703    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -1.3327    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586    0.3324    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    1.7685   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    0.3734   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    1.4023   -0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -0.5958    3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7600    0.0263    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5476    0.9048   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3443    1.1772   -1.5720 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  9 16  2  0
 16 17  1  0
  4 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 16  5  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -0.320   0.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.143   5.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.630   4.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.940   0.175   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.710   1.509   0.000  0.00  0.00           C+0
HETATM   17  F   UNK     0      -6.480   2.843   0.000  0.00  0.00           F+0
HETATM   18  F   UNK     0      -7.043   0.739   0.000  0.00  0.00           F+0
HETATM   19  F   UNK     0      -4.376   2.279   0.000  0.00  0.00           F+0
HETATM   20  N   UNK     0      -1.090   4.176   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      -3.400   0.175   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       1.650   5.553   0.000  0.00  0.00           S+0
CONECT    1   10                                                            
CONECT    2   24                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   12                                                       
CONECT    7    8   13                                                       
CONECT    8    7   20                                                       
CONECT    9   16   23                                                       
CONECT   10    1   13   14                                                  
CONECT   11    5   12   21                                                  
CONECT   12    6   11   22                                                  
CONECT   13    7   10   23                                                  
CONECT   14   10   15   20                                                  
CONECT   15   14   21   22                                                  
CONECT   16    9   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20    8   14                                                       
CONECT   21   11   15                                                       
CONECT   22   12   15   24                                                  
CONECT   23    9   13                                                       
CONECT   24    2   22                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0061003
HETATM    1  C1  UNL     1      -1.505  -0.502  -2.949  1.00  0.00           C  
HETATM    2  S1  UNL     1      -1.494   0.938  -1.821  1.00  0.00           S  
HETATM    3  N1  UNL     1      -1.945   0.475  -0.202  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.241   0.037   0.808  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.168  -0.257   1.045  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.432  -0.899   2.234  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.624  -1.224   2.682  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.714  -0.908   1.923  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.548  -0.264   0.724  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.637   0.052  -0.035  1.00  0.00           O  
HETATM   11  C7  UNL     1       4.961  -0.240   0.326  1.00  0.00           C  
HETATM   12  C8  UNL     1       5.866   0.282  -0.797  1.00  0.00           C  
HETATM   13  F1  UNL     1       7.179   0.036  -0.520  1.00  0.00           F  
HETATM   14  F2  UNL     1       5.429  -0.287  -1.966  1.00  0.00           F  
HETATM   15  F3  UNL     1       5.634   1.652  -0.894  1.00  0.00           F  
HETATM   16  C9  UNL     1       1.240   0.060   0.300  1.00  0.00           C  
HETATM   17  C10 UNL     1       1.187   0.886  -0.923  1.00  0.00           C  
HETATM   18  N3  UNL     1      -2.163  -0.292   1.804  1.00  0.00           N  
HETATM   19  C11 UNL     1      -3.386  -0.051   1.397  1.00  0.00           C  
HETATM   20  C12 UNL     1      -4.639  -0.202   2.010  1.00  0.00           C  
HETATM   21  C13 UNL     1      -5.777   0.145   1.328  1.00  0.00           C  
HETATM   22  C14 UNL     1      -5.649   0.634   0.052  1.00  0.00           C  
HETATM   23  C15 UNL     1      -4.423   0.789  -0.566  1.00  0.00           C  
HETATM   24  C16 UNL     1      -3.284   0.435   0.134  1.00  0.00           C  
HETATM   25  H1  UNL     1      -2.383  -1.140  -2.784  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.611  -1.151  -2.760  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.499  -0.151  -4.002  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.735  -1.739   3.645  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.724  -1.170   2.274  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.110  -1.333   0.455  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.259   0.332   1.239  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.556   1.768  -0.757  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.033   0.373  -1.852  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.231   1.402  -0.998  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.616  -0.596   3.016  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.760   0.026   1.808  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.548   0.905  -0.479  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.344   1.177  -1.572  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4   24
CONECT    4    5   18   18
CONECT    5    6    6   16
CONECT    6    7
CONECT    7    8    8   28
CONECT    8    9   29
CONECT    9   10   16   16
CONECT   10   11
CONECT   11   12   30   31
CONECT   12   13   14   15
CONECT   16   17
CONECT   17   32   33   34
CONECT   18   19
CONECT   19   20   20   24
CONECT   20   21   35
CONECT   21   22   22   36
CONECT   22   23   37
CONECT   23   24   24   38
END

HMDB0061003
     RDKit          3D
lansoprazole sulfide
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.5046   -0.5017   -2.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4935    0.9378   -1.8213 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448    0.4745   -0.2020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    0.0370    0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -0.2570    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321   -0.8993    2.2336 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243   -1.2236    2.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.9078    1.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.2640    0.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6365    0.0522   -0.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9609   -0.2397    0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664    0.2822   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792    0.0358   -0.5205 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4291   -0.2866   -1.9664 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6336    1.6524   -0.8941 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2398    0.0597    0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867    0.8858   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632   -0.2922    1.8036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3860   -0.0511    1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6391   -0.2022    2.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7765    0.1445    1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490    0.6340    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4233    0.7888   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840    0.4352    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -1.1396   -2.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -1.1512   -2.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -0.1505   -4.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -1.7393    3.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -1.1703    2.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1103   -1.3327    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586    0.3324    1.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564    1.7685   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    0.3734   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    1.4023   -0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -0.5958    3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7600    0.0263    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5476    0.9048   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3443    1.1772   -1.5720 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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
  9 16  2  0
 16 17  1  0
  4 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24  3  1  0
 16  5  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lansoprazole sulphide	Generator

Chemical Formula

C₁₆H₁₄F₃N₃OS

Average Molecular Weight

353.362

Monoisotopic Molecular Weight

353.08096739

IUPAC Name

2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1-(methylsulfanyl)-1H-1,3-benzodiazole

Traditional Name

2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1-(methylsulfanyl)-1,3-benzodiazole

CAS Registry Number

Not Available

SMILES

CSN1C2=CC=CC=C2N=C1C1=NC=CC(OCC(F)(F)F)=C1C

InChI Identifier

InChI=1S/C16H14F3N3OS/c1-10-13(23-9-16(17,18)19)7-8-20-14(10)15-21-11-5-3-4-6-12(11)22(15)24-2/h3-8H,9H2,1-2H3

InChI Key

RZSYMONMXLYBMJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Substituents

Benzimidazole
Alkyl aryl ether
Methylpyridine
N-substituted imidazole
Benzenoid
Pyridine
Azole
Imidazole
Heteroaromatic compound
Ether
Azacycle
Sulfenyl compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Alkyl fluoride
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organosulfur compound
Alkyl halide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0061003)
Liver (HMDB: HMDB0061003)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061003)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061003)

Cellular substructure

Cytoplasm (HMDB: HMDB0061003)
Membrane (HMDB: HMDB0061003)

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	0.0076 g/L	ALOGPS
logP	4.02	ALOGPS
logP	3.99	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.86	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.68 m³·mol⁻¹	ChemAxon
Polarizability	33.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	170.564	30932474
DeepCCS	[M-H]-	168.207	30932474
DeepCCS	[M-2H]-	201.953	30932474
DeepCCS	[M+Na]+	177.179	30932474
AllCCS	[M+H]+	177.8	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.2	32859911
AllCCS	[M+HCOO]-	171.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
lansoprazole sulfide	CSN1C2=CC=CC=C2N=C1C1=NC=CC(OCC(F)(F)F)=C1C	3063.0	Standard polar	33892256
lansoprazole sulfide	CSN1C2=CC=CC=C2N=C1C1=NC=CC(OCC(F)(F)F)=C1C	2353.8	Standard non polar	33892256
lansoprazole sulfide	CSN1C2=CC=CC=C2N=C1C1=NC=CC(OCC(F)(F)F)=C1C	2440.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - lansoprazole sulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9i-2369000000-32ef57ffe8f2fcaf5cc0	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - lansoprazole sulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - lansoprazole sulfide 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 - lansoprazole sulfide 10V, Positive-QTOF	splash10-0ue9-5109000000-81e60f66f5d881c43fc7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 20V, Positive-QTOF	splash10-0udi-4339000000-eaf602062140261f6f6e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 40V, Positive-QTOF	splash10-001i-9310000000-17e01773452df1592f37	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 10V, Negative-QTOF	splash10-0udi-1009000000-7dd7db44c215a5494261	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 20V, Negative-QTOF	splash10-0k95-9028000000-17f5ad2cd1d08d052937	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 40V, Negative-QTOF	splash10-0a4l-0940000000-51641110566645108d22	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 10V, Positive-QTOF	splash10-0udi-0009000000-fb1273863c963cf419d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 20V, Positive-QTOF	splash10-0udi-0009000000-57e1fdccb6454961cefa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 40V, Positive-QTOF	splash10-0006-1890000000-18a38dcd7c1118f4d602	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 10V, Negative-QTOF	splash10-0udi-0109000000-140500338a1f13d087bc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 20V, Negative-QTOF	splash10-0zfr-0079000000-26851273fa7439cc362d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - lansoprazole sulfide 40V, Negative-QTOF	splash10-0k9l-0592000000-6126f2a078c1be8bcea1	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

44181912

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 lansoprazole sulfide (HMDB0061003)

MOL for HMDB0061003 (lansoprazole sulfide)

3D MOL for HMDB0061003 (lansoprazole sulfide)

3D SDF for HMDB0061003 (lansoprazole sulfide)

3D-SDF for HMDB0061003 (lansoprazole sulfide)

PDB for HMDB0061003 (lansoprazole sulfide)

3D PDB for HMDB0061003 (lansoprazole sulfide)

SMILES for HMDB0061003 (lansoprazole sulfide)

INCHI for HMDB0061003 (lansoprazole sulfide)

Structure for HMDB0061003 (lansoprazole sulfide)

3D Structure for HMDB0061003 (lansoprazole sulfide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra