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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (3) Show 14 proteins XML

enzymes (11)transporters (3) Show 14 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:49 UTC

Update Date

2020-02-26 21:39:20 UTC

HMDB ID

HMDB0014010

Secondary Accession Numbers

HMDB14010

Metabolite Identification

Common Name

5-Hydroxyomeprazole

Description

5-Hydroxyomeprazole is only found in individuals that have used or taken Omeprazole. 5-Hydroxyomeprazole is a metabolite of Omeprazole. 5-hydroxyomeprazole belongs to the family of Sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.

Structure

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

HMDB0014010
     RDKit          3D
5-Hydroxyomeprazole
 44 46  0  0  0  0  0  0  0  0999 V2000
    8.8235   -0.1636   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.7774    0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444   -0.3749    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473    0.7297   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8016    1.1545   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    0.4882    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    0.6966    0.1946 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -0.2275    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2568   -0.3960    1.5426 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.0240    0.5104    2.7438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492   -0.0230    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.1897    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -0.5670    1.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781   -0.7606    1.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.6040    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3504   -0.9439    1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9090   -0.0360    2.1180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -0.2321   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4221   -0.1138   -1.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0397    1.0194   -1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648   -0.0152   -0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    0.6151   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -1.0184    1.3386 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.6427    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -1.0562    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1588    0.7752    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6509   -0.9323   -0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4831    0.1498   -1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920    1.2632   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    1.9929   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711    1.0908   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -0.6329   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564   -1.0792    2.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9555   -1.3059    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -1.8762    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6023    0.8806    1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0015    1.9244   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1624    0.7702   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7185    1.1789   -2.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    0.8669   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2675    1.6606   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.0288   -2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528   -1.8956    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6664   -1.9324    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
  8 23  1  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  6  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
M  END


  Mrv0541 06191310392D          

 25 27  0  0  0  0            999 V2000
    9.1275   -3.1633    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.0150   -5.3067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5400   -2.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -2.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -2.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -3.8272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7775   -3.1633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5400   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3650   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7775   -4.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3025   -3.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405   -2.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6025   -4.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405   -3.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0150   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3650   -5.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260   -2.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6025   -3.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260   -3.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -2.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -3.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8400   -3.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8400   -5.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1825   -2.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2525   -3.1633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  2 13  1  0  0  0  0
  2 23  1  0  0  0  0
  4 20  1  0  0  0  0
  4 24  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 11  2  0  0  0  0
  6 14  1  0  0  0  0
  7  9  2  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  2  0  0  0  0
 10 16  1  0  0  0  0
 12 14  2  0  0  0  0
 12 17  1  0  0  0  0
 13 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 18  2  0  0  0  0
 15 22  1  0  0  0  0
 17 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 22 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014010

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(CO)C(OC)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C17H19N3O4S/c1-10-15(18-7-11(8-21)16(10)24-3)9-25(22)17-19-13-5-4-12(23-2)6-14(13)20-17/h4-7,21H,8-9H2,1-3H3,(H,19,20)

> <INCHI_KEY>
CMZHQFXXAAIBKE-UHFFFAOYSA-N

> <FORMULA>
C17H19N3O4S

> <MOLECULAR_WEIGHT>
361.415

> <EXACT_MASS>
361.109626801

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
38.431762463245654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4-methoxy-6-{[(6-methoxy-1H-1,3-benzodiazol-2-yl)sulfinyl]methyl}-5-methylpyridin-3-yl)methanol

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
1.1527379666666664

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.415214855701123

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.294143138752593

> <JCHEM_PKA_STRONGEST_BASIC>
3.9285008509227963

> <JCHEM_POLAR_SURFACE_AREA>
97.33000000000001

> <JCHEM_REFRACTIVITY>
95.437

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-methoxy-6-[(5-methoxy-3H-1,3-benzodiazol-2-ylsulfinyl)methyl]-5-methylpyridin-3-yl}methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014010
     RDKit          3D
5-Hydroxyomeprazole
 44 46  0  0  0  0  0  0  0  0999 V2000
    8.8235   -0.1636   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.7774    0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444   -0.3749    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473    0.7297   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8016    1.1545   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    0.4882    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    0.6966    0.1946 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -0.2275    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2568   -0.3960    1.5426 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.0240    0.5104    2.7438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492   -0.0230    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.1897    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -0.5670    1.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781   -0.7606    1.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.6040    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3504   -0.9439    1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9090   -0.0360    2.1180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -0.2321   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4221   -0.1138   -1.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0397    1.0194   -1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648   -0.0152   -0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    0.6151   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -1.0184    1.3386 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.6427    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -1.0562    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1588    0.7752    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6509   -0.9323   -0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4831    0.1498   -1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920    1.2632   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    1.9929   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711    1.0908   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -0.6329   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564   -1.0792    2.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9555   -1.3059    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -1.8762    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6023    0.8806    1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0015    1.9244   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1624    0.7702   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7185    1.1789   -2.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    0.8669   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2675    1.6606   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.0288   -2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528   -1.8956    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6664   -1.9324    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
  8 23  1  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  6  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  S   UNK     0      17.038  -5.905   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      22.428  -9.906   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      17.808  -4.571   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.141  -4.365   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      14.599  -4.666   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      14.599  -7.144   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      20.118  -5.905   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      17.808  -7.238   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.348  -7.238   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.118  -8.572   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.498  -5.905   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.142  -5.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.658  -8.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.142  -6.675   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.428  -7.238   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.348  -9.906   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.808  -4.365   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.658  -5.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.808  -7.445   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.475  -5.135   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.475  -6.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.968  -7.238   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.968  -9.906   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.807  -5.135   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      24.738  -5.905   0.000  0.00  0.00           O+0
CONECT    1    3    8   11                                                  
CONECT    2   13   23                                                       
CONECT    3    1                                                            
CONECT    4   20   24                                                       
CONECT    5   11   12                                                       
CONECT    6   11   14                                                       
CONECT    7    9   18                                                       
CONECT    8    1    9                                                       
CONECT    9    7    8   10                                                  
CONECT   10    9   13   16                                                  
CONECT   11    1    5    6                                                  
CONECT   12    5   14   17                                                  
CONECT   13    2   10   15                                                  
CONECT   14    6   12   19                                                  
CONECT   15   13   18   22                                                  
CONECT   16   10                                                            
CONECT   17   12   20                                                       
CONECT   18    7   15                                                       
CONECT   19   14   21                                                       
CONECT   20    4   17   21                                                  
CONECT   21   19   20                                                       
CONECT   22   15   25                                                       
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0061091
HETATM    1  C1  UNL     1       8.530   0.874  -0.060  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.139   1.235  -0.221  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.124   0.392   0.132  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.286  -0.831   0.672  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.130  -1.591   0.980  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.862  -1.133   0.752  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.597  -1.667   0.837  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.713  -0.716   0.349  1.00  0.00           C  
HETATM    9  S1  UNL     1      -0.029  -0.821   0.265  1.00  0.00           S  
HETATM   10  O2  UNL     1      -0.696  -1.296   1.491  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.594   0.855  -0.196  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.037   0.973  -0.164  1.00  0.00           C  
HETATM   13  N2  UNL     1      -2.583   2.130   0.246  1.00  0.00           N  
HETATM   14  C9  UNL     1      -3.887   2.299   0.512  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.706   1.236   0.351  1.00  0.00           C  
HETATM   16  C11 UNL     1      -6.182   1.245   0.673  1.00  0.00           C  
HETATM   17  O3  UNL     1      -6.870   2.193  -0.070  1.00  0.00           O  
HETATM   18  C12 UNL     1      -4.190   0.023  -0.069  1.00  0.00           C  
HETATM   19  O4  UNL     1      -5.079  -1.013  -0.189  1.00  0.00           O  
HETATM   20  C13 UNL     1      -5.913  -1.495  -1.146  1.00  0.00           C  
HETATM   21  C14 UNL     1      -2.901  -0.112  -0.328  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.316  -1.336  -1.011  1.00  0.00           C  
HETATM   23  N3  UNL     1       2.470   0.325  -0.007  1.00  0.00           N  
HETATM   24  C16 UNL     1       3.748   0.118   0.202  1.00  0.00           C  
HETATM   25  C17 UNL     1       4.830   0.890  -0.110  1.00  0.00           C  
HETATM   26  H1  UNL     1       8.626  -0.211  -0.042  1.00  0.00           H  
HETATM   27  H2  UNL     1       9.102   1.516   0.550  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.965   1.148  -1.154  1.00  0.00           H  
HETATM   29  H4  UNL     1       7.240  -1.300   0.840  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.257  -2.573   1.419  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.000   1.344  -0.945  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.274   1.433   0.772  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.310   3.266   0.867  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.522   0.392   1.152  1.00  0.00           H  
HETATM   35  H10 UNL     1      -6.119   2.001   1.690  1.00  0.00           H  
HETATM   36  H11 UNL     1      -7.809   2.317   0.147  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.990  -0.795  -2.014  1.00  0.00           H  
HETATM   38  H13 UNL     1      -6.968  -1.668  -0.705  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.611  -2.471  -1.527  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.524  -0.988  -1.753  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.151  -2.236  -0.486  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.163  -1.610  -1.761  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.046   1.165  -0.439  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.760   1.872  -0.503  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   24
CONECT    7    8    8
CONECT    8    9   23
CONECT    9   10   10   11
CONECT   11   12   31   32
CONECT   12   13   13   21
CONECT   13   14
CONECT   14   15   15   33
CONECT   15   16   18
CONECT   16   17   34   35
CONECT   17   36
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   37   38   39
CONECT   21   22
CONECT   22   40   41   42
CONECT   23   24   43
CONECT   24   25   25
CONECT   25   44
END

HMDB0014010
     RDKit          3D
5-Hydroxyomeprazole
 44 46  0  0  0  0  0  0  0  0999 V2000
    8.8235   -0.1636   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -0.7774    0.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444   -0.3749    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473    0.7297   -0.5529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8016    1.1545   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    0.4882    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    0.6966    0.1946 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -0.2275    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2568   -0.3960    1.5426 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.0240    0.5104    2.7438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492   -0.0230    0.1965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.1897    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6786   -0.5670    1.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9781   -0.7606    1.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232   -0.6040    0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3504   -0.9439    1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9090   -0.0360    2.1180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5253   -0.2321   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4221   -0.1138   -1.3241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0397    1.0194   -1.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648   -0.0152   -0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    0.6151   -1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -1.0184    1.3386 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -0.6427    0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -1.0562    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1588    0.7752    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6509   -0.9323   -0.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4831    0.1498   -1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920    1.2632   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    1.9929   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6711    1.0908   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5645   -0.6329   -0.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564   -1.0792    2.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9555   -1.3059    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2187   -1.8762    1.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6023    0.8806    1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0015    1.9244   -1.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1624    0.7702   -1.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7185    1.1789   -2.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004    0.8669   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2675    1.6606   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    0.0288   -2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528   -1.8956    1.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6664   -1.9324    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
  8 23  1  0
 23 24  1  0
 24 25  2  0
 25  3  1  0
 24  6  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 25 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Methoxy-2-(((4-methoxy-3-methyl-5-hydroxymethyl-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole	ChEBI
Hydroxyomeprazole	ChEBI
5-Methoxy-2-(((4-methoxy-3-methyl-5-hydroxymethyl-2-pyridinyl)methyl)sulphinyl)-1H-benzimidazole	Generator
5-Hydroxy omeprazole	HMDB
5-Hydroxymethylomeprazole	HMDB

Chemical Formula

C₁₇H₁₉N₃O₄S

Average Molecular Weight

361.415

Monoisotopic Molecular Weight

361.109626801

IUPAC Name

(4-methoxy-6-{[(6-methoxy-1H-1,3-benzodiazol-2-yl)sulfinyl]methyl}-5-methylpyridin-3-yl)methanol

Traditional Name

{4-methoxy-6-[(5-methoxy-3H-1,3-benzodiazol-2-ylsulfinyl)methyl]-5-methylpyridin-3-yl}methanol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(CO)C(OC)=C1C

InChI Identifier

InChI=1S/C17H19N3O4S/c1-10-15(18-7-11(8-21)16(10)24-3)9-25(22)17-19-13-5-4-12(23-2)6-14(13)20-17/h4-7,21H,8-9H2,1-3H3,(H,19,20)

InChI Key

CMZHQFXXAAIBKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Sulfinylbenzimidazoles

Direct Parent

Sulfinylbenzimidazoles

Alternative Parents

Substituents

Sulfinylbenzimidazole
Anisole
Alkyl aryl ether
Methylpyridine
Pyridine
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Sulfoxide
Sulfinyl compound
Ether
Azacycle
Aromatic alcohol
Organic oxide
Organopnictogen compound
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:63840 )
sulfoxide (CHEBI:63840 )
pyridines (CHEBI:63840 )
benzimidazoles (CHEBI:63840 )

Ontology

Not Available

Liver (HMDB: HMDB0014010)
Kidney (HMDB: HMDB0014010)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014010)

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	0.75 g/L	ALOGPS
logP	1.05	ALOGPS
logP	1.15	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	3.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.33 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.44 m³·mol⁻¹	ChemAxon
Polarizability	38.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	183.717	31661259
DarkChem	[M-H]-	184.084	31661259
DeepCCS	[M+H]+	185.228	30932474
DeepCCS	[M-H]-	182.87	30932474
DeepCCS	[M-2H]-	216.83	30932474
DeepCCS	[M+Na]+	192.058	30932474
AllCCS	[M+H]+	184.5	32859911
AllCCS	[M+H-H2O]+	181.6	32859911
AllCCS	[M+NH4]+	187.2	32859911
AllCCS	[M+Na]+	187.9	32859911
AllCCS	[M-H]-	183.7	32859911
AllCCS	[M+Na-2H]-	183.7	32859911
AllCCS	[M+HCOO]-	183.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxyomeprazole	COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(CO)C(OC)=C1C	4344.8	Standard polar	33892256
5-Hydroxyomeprazole	COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(CO)C(OC)=C1C	3369.7	Standard non polar	33892256
5-Hydroxyomeprazole	COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(CO)C(OC)=C1C	3524.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxyomeprazole,1TMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C)C(OC)=C3C)[NH]C2=C1	3272.2	Semi standard non polar	33892256
5-Hydroxyomeprazole,1TMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C)C(OC)=C3C)[NH]C2=C1	3272.2	Semi standard non polar	33892256
5-Hydroxyomeprazole,1TMS,isomer #2	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO)C(OC)=C3C)N([Si](C)(C)C)C2=C1	3241.4	Semi standard non polar	33892256
5-Hydroxyomeprazole,1TMS,isomer #2	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO)C(OC)=C3C)N([Si](C)(C)C)C2=C1	3241.4	Semi standard non polar	33892256
5-Hydroxyomeprazole,2TMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C)C(OC)=C3C)N([Si](C)(C)C)C2=C1	3268.4	Semi standard non polar	33892256
5-Hydroxyomeprazole,2TMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C)C(OC)=C3C)N([Si](C)(C)C)C2=C1	3199.1	Standard non polar	33892256
5-Hydroxyomeprazole,2TMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C)C(OC)=C3C)N([Si](C)(C)C)C2=C1	3994.0	Standard polar	33892256
5-Hydroxyomeprazole,1TBDMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C(C)(C)C)C(OC)=C3C)[NH]C2=C1	3476.0	Semi standard non polar	33892256
5-Hydroxyomeprazole,1TBDMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C(C)(C)C)C(OC)=C3C)[NH]C2=C1	3476.0	Semi standard non polar	33892256
5-Hydroxyomeprazole,1TBDMS,isomer #2	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO)C(OC)=C3C)N([Si](C)(C)C(C)(C)C)C2=C1	3427.5	Semi standard non polar	33892256
5-Hydroxyomeprazole,1TBDMS,isomer #2	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO)C(OC)=C3C)N([Si](C)(C)C(C)(C)C)C2=C1	3427.5	Semi standard non polar	33892256
5-Hydroxyomeprazole,2TBDMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C(C)(C)C)C(OC)=C3C)N([Si](C)(C)C(C)(C)C)C2=C1	3571.2	Semi standard non polar	33892256
5-Hydroxyomeprazole,2TBDMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C(C)(C)C)C(OC)=C3C)N([Si](C)(C)C(C)(C)C)C2=C1	3607.7	Standard non polar	33892256
5-Hydroxyomeprazole,2TBDMS,isomer #1	COC1=CC=C2N=C(S(=O)CC3=NC=C(CO[Si](C)(C)C(C)(C)C)C(OC)=C3C)N([Si](C)(C)C(C)(C)C)C2=C1	4059.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyomeprazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-0903000000-9ecfcf6e9345c41269b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyomeprazole GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6962300000-aceff1ef59d217de913e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyomeprazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxyomeprazole 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 - 5-Hydroxyomeprazole 10V, Positive-QTOF	splash10-03dl-0129000000-63b3da2a877ed49bac04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 20V, Positive-QTOF	splash10-01oy-0938000000-921769315297d14c7ef9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 40V, Positive-QTOF	splash10-0udi-2900000000-464e1df97777a9c0f193	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 10V, Negative-QTOF	splash10-03dj-0609000000-347b6db613e118706276	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 20V, Negative-QTOF	splash10-002b-0901000000-62a5cbcb1ba7d17112ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 40V, Negative-QTOF	splash10-004j-0901000000-364ea8566e3d1bc71711	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 10V, Positive-QTOF	splash10-03di-0149000000-7ad8af4381497afe6605	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 20V, Positive-QTOF	splash10-01ot-0922000000-5c069a336cea040547be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 40V, Positive-QTOF	splash10-0002-0900000000-03fd40a397848d26077c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 10V, Negative-QTOF	splash10-0007-0709000000-2c9a64f03d50c26c5248	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 20V, Negative-QTOF	splash10-0005-0901000000-60d76e6f1c3f7a156375	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxyomeprazole 40V, Negative-QTOF	splash10-001i-1900000000-80e82c5e8ad4ca59031c	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Omeprazole Action Pathway		Not Available

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

106763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119560

PDB ID

Not Available

ChEBI ID

63840

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

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

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 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

Li XQ, Weidolf L, Simonsson R, Andersson TB: Enantiomer/enantiomer interactions between the S- and R- isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther. 2005 Nov;315(2):777-87. Epub 2005 Aug 10. [PubMed:16093273 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. [PubMed:8423765 ]
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 ]
Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [PubMed:15626586 ]

Enzyme Details

3. 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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Foti RS, Wahlstrom JL: CYP2C19 inhibition: the impact of substrate probe selection on in vitro inhibition profiles. Drug Metab Dispos. 2008 Mar;36(3):523-8. Epub 2007 Nov 29. [PubMed:18048485 ]
Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [PubMed:15258107 ]
Li XQ, Weidolf L, Simonsson R, Andersson TB: Enantiomer/enantiomer interactions between the S- and R- isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther. 2005 Nov;315(2):777-87. Epub 2005 Aug 10. [PubMed:16093273 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 ]
Yamazaki H, Inoue K, Shaw PM, Checovich WJ, Guengerich FP, Shimada T: Different contributions of cytochrome P450 2C19 and 3A4 in the oxidation of omeprazole by human liver microsomes: effects of contents of these two forms in individual human samples. J Pharmacol Exp Ther. 1997 Nov;283(2):434-42. [PubMed:9353355 ]

Enzyme Details

5. Potassium-transporting ATPase alpha chain 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach.
Gene Name:: ATP4A
Uniprot ID:: P20648
Molecular weight:: 114117.74

References

Tajima A, Koizumi K, Suzuki K, Higashi N, Takahashi M, Shimada T, Terano A, Hiraishi H, Kuwayama H: Proton pump inhibitors and recurrent bleeding in peptic ulcer disease. J Gastroenterol Hepatol. 2008 Dec;23 Suppl 2:S237-41. doi: 10.1111/j.1440-1746.2008.05557.x. [PubMed:19120905 ]
Shi S, Klotz U: Proton pump inhibitors: an update of their clinical use and pharmacokinetics. Eur J Clin Pharmacol. 2008 Oct;64(10):935-51. doi: 10.1007/s00228-008-0538-y. Epub 2008 Aug 5. [PubMed:18679668 ]
Kirchheiner J, Glatt S, Fuhr U, Klotz U, Meineke I, Seufferlein T, Brockmoller J: Relative potency of proton-pump inhibitors-comparison of effects on intragastric pH. Eur J Clin Pharmacol. 2009 Jan;65(1):19-31. doi: 10.1007/s00228-008-0576-5. Epub 2008 Oct 17. [PubMed:18925391 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

6. Cytochrome P450 1B1

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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

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

7. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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

8. Cytochrome P450 2C18

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.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

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

9. Cytochrome P450 1A1

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.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

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

10. 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 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Hitzl M, Klein K, Zanger UM, Fritz P, Nussler AK, Neuhaus P, Fromm MF: Influence of omeprazole on multidrug resistance protein 3 expression in human liver. J Pharmacol Exp Ther. 2003 Feb;304(2):524-30. [PubMed:12538803 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [PubMed:11770010 ]

Enzyme Details

3. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Breedveld P, Zelcer N, Pluim D, Sonmezer O, Tibben MM, Beijnen JH, Schinkel AH, van Tellingen O, Borst P, Schellens JH: Mechanism of the pharmacokinetic interaction between methotrexate and benzimidazoles: potential role for breast cancer resistance protein in clinical drug-drug interactions. Cancer Res. 2004 Aug 15;64(16):5804-11. [PubMed:15313923 ]
Suzuki K, Doki K, Homma M, Tamaki H, Hori S, Ohtani H, Sawada Y, Kohda Y: Co-administration of proton pump inhibitors delays elimination of plasma methotrexate in high-dose methotrexate therapy. Br J Clin Pharmacol. 2009 Jan;67(1):44-9. doi: 10.1111/j.1365-2125.2008.03303.x. Epub 2008 Nov 17. [PubMed:19076159 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for 5-Hydroxyomeprazole (HMDB0014010)

MOL for HMDB0014010 (5-Hydroxyomeprazole)

3D MOL for HMDB0014010 (5-Hydroxyomeprazole)

3D SDF for HMDB0014010 (5-Hydroxyomeprazole)

3D-SDF for HMDB0014010 (5-Hydroxyomeprazole)

PDB for HMDB0014010 (5-Hydroxyomeprazole)

3D PDB for HMDB0014010 (5-Hydroxyomeprazole)

SMILES for HMDB0014010 (5-Hydroxyomeprazole)

INCHI for HMDB0014010 (5-Hydroxyomeprazole)

Structure for HMDB0014010 (5-Hydroxyomeprazole)

3D Structure for HMDB0014010 (5-Hydroxyomeprazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

References

Transporters

References

References

References