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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (3) Show 11 proteins XML

enzymes (8)transporters (3) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015108

Secondary Accession Numbers

HMDB15108

Metabolite Identification

Common Name

Ezetimibe

Description

Ezetimibe, also known as zetia or ezedoc, belongs to the class of organic compounds known as monobactams. Monobactams are compounds comprising beta-lactam ring is alone and not fused to another ring. Ezetimibe is an extremely weak basic (essentially neutral) compound (based on its pKa). A beta-lactam that is azetidin-2-one which is substituted at 1, 3, and 4 by p-fluorophenyl, 3-(p-fluorophenyl)-3-hydroxypropyl, and 4-hydroxyphenyl groups, respectively (the 3R,3'S,4S enantiomer).

Structure

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

973
  Mrv0541 02231215082D          

 30 33  0  0  1  0            999 V2000
    1.6500    0.2834    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8294    3.8558    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    1.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5919    0.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    0.2834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1168    0.2834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5335   -0.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9419    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3544    0.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1794    0.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2479   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8190   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -0.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    0.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5919    1.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2479   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8190   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1794    2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    1.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5919    3.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8294    2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    3.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 30  1  0  0  0  0
  3 10  2  0  0  0  0
 14  4  1  1  0  0  0
  5 22  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
  8 11  1  1  0  0  0
  9 12  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 14  1  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 23  1  0  0  0  0
 18 24  2  0  0  0  0
 19 25  2  0  0  0  0
 19 26  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 27  2  0  0  0  0
 24 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0015108
     RDKit          3D
Ezetimibe
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5934    0.5274   -2.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    0.3776   -1.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4616   -0.0444   -1.4658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5073    1.1211   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    0.5394   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.5894   -0.8623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5102    2.4373    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    0.9488   -0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363   -0.3981   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5994   -0.9979   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5703   -0.2289    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7335   -0.7970    0.9724 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351    1.1172    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1792    1.7029    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -0.5019   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6819   -1.8572   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412   -2.8853   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745   -4.1301   -0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -4.3328   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -5.6038   -0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -3.2691    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -2.0167    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405    0.5645   -0.3805 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.4373    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695    2.0156   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792    2.8796    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505    3.1751    1.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    4.0084    2.6401 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191    2.5942    2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.7475    1.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -0.8829   -2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    1.5723   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    1.8623   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -0.0995   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.1177   -1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.2030   -1.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7191    1.9966    1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6734   -1.0239   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7399   -2.0596   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0975    1.7517    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645    2.7701    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665   -0.3133    0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842   -2.7506   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336   -4.9161   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -6.3069    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560   -3.4601    0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -1.1824    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    1.8235   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6547    3.3123    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0278    2.8073    3.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347    1.2938    2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  3 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 23  2  1  0
 30 24  1  0
 14  8  1  0
 22 16  1  0
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  1
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 29 50  1  0
 30 51  1  0
M  END

973
  Mrv0541 02231215082D          

 30 33  0  0  1  0            999 V2000
    1.6500    0.2834    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8294    3.8558    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    1.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5919    0.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    0.2834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1168    0.2834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5335   -0.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9419    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3544    0.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1794    0.9979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2479   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8190   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -0.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    0.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5919    1.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2479   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8190   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876   -0.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1794    2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    1.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5919    3.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8294    2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4169    3.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 30  1  0  0  0  0
  3 10  2  0  0  0  0
 14  4  1  1  0  0  0
  5 22  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
  8 11  1  1  0  0  0
  9 12  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 14  1  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 23  1  0  0  0  0
 18 24  2  0  0  0  0
 19 25  2  0  0  0  0
 19 26  1  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 27  2  0  0  0  0
 24 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  2  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015108

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1

> <INCHI_KEY>
OLNTVTPDXPETLC-XPWALMASSA-N

> <FORMULA>
C24H21F2NO3

> <MOLECULAR_WEIGHT>
409.4252

> <EXACT_MASS>
409.148949953

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.64226474732217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
4.559127928333334

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.443302513576896

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.484298994388533

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0422882951353873

> <JCHEM_POLAR_SURFACE_AREA>
60.77

> <JCHEM_REFRACTIVITY>
108.86170000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ezetimibe

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015108
     RDKit          3D
Ezetimibe
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5934    0.5274   -2.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    0.3776   -1.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4616   -0.0444   -1.4658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5073    1.1211   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    0.5394   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.5894   -0.8623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5102    2.4373    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    0.9488   -0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363   -0.3981   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5994   -0.9979   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5703   -0.2289    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7335   -0.7970    0.9724 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351    1.1172    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1792    1.7029    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -0.5019   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6819   -1.8572   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412   -2.8853   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745   -4.1301   -0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -4.3328   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -5.6038   -0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -3.2691    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -2.0167    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405    0.5645   -0.3805 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.4373    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695    2.0156   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792    2.8796    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505    3.1751    1.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    4.0084    2.6401 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191    2.5942    2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.7475    1.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -0.8829   -2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    1.5723   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    1.8623   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -0.0995   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.1177   -1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.2030   -1.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7191    1.9966    1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6734   -1.0239   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7399   -2.0596   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0975    1.7517    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645    2.7701    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665   -0.3133    0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842   -2.7506   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336   -4.9161   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -6.3069    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560   -3.4601    0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -1.1824    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    1.8235   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6547    3.3123    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0278    2.8073    3.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347    1.2938    2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  3 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 23  2  1  0
 30 24  1  0
 14  8  1  0
 22 16  1  0
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  1
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 29 50  1  0
 30 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 973                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.080   0.529   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0      18.348   7.197   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0      10.329   3.158   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.038   0.529   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.329  -6.720   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.240   0.529   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.418   0.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.329  -0.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.958   0.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.329   1.618   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.329  -2.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.728   1.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.700   0.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.268   1.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.663  -2.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.995  -2.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.930  -0.805   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.930   1.863   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.038   3.196   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.663  -4.410   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.995  -4.410   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.329  -5.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.390  -0.805   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.390   1.863   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.268   4.530   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.578   3.196   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.620   0.529   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.038   5.864   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.348   4.530   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.578   5.864   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2   30                                                            
CONECT    3   10                                                            
CONECT    4   14                                                            
CONECT    5   22                                                            
CONECT    6    8   10   13                                                  
CONECT    7    8    9   10                                                  
CONECT    8    6    7   11                                                  
CONECT    9    7   12                                                       
CONECT   10    3    6    7                                                  
CONECT   11    8   15   16                                                  
CONECT   12    9   14                                                       
CONECT   13    6   17   18                                                  
CONECT   14    4   12   19                                                  
CONECT   15   11   20                                                       
CONECT   16   11   21                                                       
CONECT   17   13   23                                                       
CONECT   18   13   24                                                       
CONECT   19   14   25   26                                                  
CONECT   20   15   22                                                       
CONECT   21   16   22                                                       
CONECT   22    5   20   21                                                  
CONECT   23   17   27                                                       
CONECT   24   18   27                                                       
CONECT   25   19   28                                                       
CONECT   26   19   29                                                       
CONECT   27    1   23   24                                                  
CONECT   28   25   30                                                       
CONECT   29   26   30                                                       
CONECT   30    2   28   29                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015108
HETATM    1  O1  UNL     1       2.593   0.527  -2.792  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.853   0.378  -1.785  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.462  -0.044  -1.466  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.507   1.121  -1.337  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.866   0.539  -1.013  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.922   1.589  -0.862  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.510   2.437   0.194  1.00  0.00           O  
HETATM    8  C6  UNL     1      -4.177   0.949  -0.385  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.436  -0.398  -0.510  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.599  -0.998  -0.071  1.00  0.00           C  
HETATM   11  C9  UNL     1      -6.570  -0.229   0.528  1.00  0.00           C  
HETATM   12  F1  UNL     1      -7.734  -0.797   0.972  1.00  0.00           F  
HETATM   13  C10 UNL     1      -6.335   1.117   0.665  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.179   1.703   0.227  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.070  -0.502  -0.181  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.682  -1.857  -0.226  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.041  -2.885  -0.876  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.675  -4.130  -0.889  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.888  -4.333  -0.281  1.00  0.00           C  
HETATM   20  O3  UNL     1       3.441  -5.604  -0.346  1.00  0.00           O  
HETATM   21  C17 UNL     1       3.485  -3.269   0.355  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.915  -2.017   0.405  1.00  0.00           C  
HETATM   23  N1  UNL     1       2.040   0.564  -0.380  1.00  0.00           N  
HETATM   24  C19 UNL     1       2.846   1.437   0.385  1.00  0.00           C  
HETATM   25  C20 UNL     1       3.969   2.016  -0.137  1.00  0.00           C  
HETATM   26  C21 UNL     1       4.779   2.880   0.598  1.00  0.00           C  
HETATM   27  C22 UNL     1       4.451   3.175   1.905  1.00  0.00           C  
HETATM   28  F2  UNL     1       5.216   4.008   2.640  1.00  0.00           F  
HETATM   29  C23 UNL     1       3.319   2.594   2.433  1.00  0.00           C  
HETATM   30  C24 UNL     1       2.531   1.747   1.703  1.00  0.00           C  
HETATM   31  H1  UNL     1       0.091  -0.883  -2.068  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.568   1.572  -2.350  1.00  0.00           H  
HETATM   33  H3  UNL     1      -0.175   1.862  -0.613  1.00  0.00           H  
HETATM   34  H4  UNL     1      -1.775  -0.099  -0.130  1.00  0.00           H  
HETATM   35  H5  UNL     1      -2.110  -0.118  -1.894  1.00  0.00           H  
HETATM   36  H6  UNL     1      -3.072   2.203  -1.750  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.719   1.997   1.056  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.673  -1.024  -0.984  1.00  0.00           H  
HETATM   39  H9  UNL     1      -5.740  -2.060  -0.200  1.00  0.00           H  
HETATM   40  H10 UNL     1      -7.098   1.752   1.142  1.00  0.00           H  
HETATM   41  H11 UNL     1      -4.964   2.770   0.321  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.467  -0.313   0.708  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.084  -2.751  -1.358  1.00  0.00           H  
HETATM   44  H14 UNL     1       1.134  -4.916  -1.414  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.255  -6.307   0.359  1.00  0.00           H  
HETATM   46  H16 UNL     1       4.456  -3.460   0.832  1.00  0.00           H  
HETATM   47  H17 UNL     1       3.402  -1.182   0.916  1.00  0.00           H  
HETATM   48  H18 UNL     1       4.269   1.823  -1.140  1.00  0.00           H  
HETATM   49  H19 UNL     1       5.655   3.312   0.149  1.00  0.00           H  
HETATM   50  H20 UNL     1       3.028   2.807   3.469  1.00  0.00           H  
HETATM   51  H21 UNL     1       1.635   1.294   2.135  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4   15   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    8   36
CONECT    7   37
CONECT    8    9    9   14
CONECT    9   10   38
CONECT   10   11   11   39
CONECT   11   12   13
CONECT   13   14   14   40
CONECT   14   41
CONECT   15   16   23   42
CONECT   16   17   17   22
CONECT   17   18   43
CONECT   18   19   19   44
CONECT   19   20   21
CONECT   20   45
CONECT   21   22   22   46
CONECT   22   47
CONECT   23   24
CONECT   24   25   25   30
CONECT   25   26   48
CONECT   26   27   27   49
CONECT   27   28   29
CONECT   29   30   30   50
CONECT   30   51
END

HMDB0015108
     RDKit          3D
Ezetimibe
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.5934    0.5274   -2.7919 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526    0.3776   -1.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4616   -0.0444   -1.4658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5073    1.1211   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8657    0.5394   -1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.5894   -0.8623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5102    2.4373    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    0.9488   -0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363   -0.3981   -0.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5994   -0.9979   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5703   -0.2289    0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7335   -0.7970    0.9724 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3351    1.1172    0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1792    1.7029    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0698   -0.5019   -0.1811 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6819   -1.8572   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0412   -2.8853   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6745   -4.1301   -0.8889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879   -4.3328   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -5.6038   -0.3456 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -3.2691    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -2.0167    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405    0.5645   -0.3805 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.4373    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695    2.0156   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792    2.8796    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4505    3.1751    1.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2160    4.0084    2.6401 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191    2.5942    2.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    1.7475    1.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0911   -0.8829   -2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    1.5723   -2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1749    1.8623   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752   -0.0995   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096   -0.1177   -1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.2030   -1.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7191    1.9966    1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6734   -1.0239   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7399   -2.0596   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0975    1.7517    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645    2.7701    0.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665   -0.3133    0.7078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842   -2.7506   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1336   -4.9161   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550   -6.3069    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560   -3.4601    0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -1.1824    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    1.8235   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6547    3.3123    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0278    2.8073    3.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347    1.2938    2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  3 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 15 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 23  2  1  0
 30 24  1  0
 14  8  1  0
 22 16  1  0
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  6
  7 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  1
 17 43  1  0
 18 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 29 50  1  0
 30 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ezedoc	ChEBI
Ezetimiba	ChEBI
Ezetimibum	ChEBI
Ezetrol	ChEBI
Zetia	ChEBI
(1-(4-Fluorophenyl)-(3R)-(3-(4-fluorophenyl)-(3S)-hydroxypropyl)-(4S)-(4-hydroxyphenyl)-2-azetidinone)	HMDB
Ezetimib	HMDB

Chemical Formula

C₂₄H₂₁F₂NO₃

Average Molecular Weight

409.4252

Monoisotopic Molecular Weight

409.148949953

IUPAC Name

(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one

Traditional Name

ezetimibe

CAS Registry Number

163222-33-1

SMILES

O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1

InChI Key

OLNTVTPDXPETLC-XPWALMASSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monobactams. Monobactams are compounds comprising beta-lactam ring is alone and not fused to another ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Monobactams

Alternative Parents

Substituents

Monobactam
1-phenylazetidine
2-phenylazetidine
1-hydroxy-2-unsubstituted benzenoid
Fluorobenzene
Halobenzene
Phenol
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Secondary alcohol
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:49040 )
azetidines (CHEBI:49040 )
beta-lactam (CHEBI:49040 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015108)
Membrane (HMDB: HMDB0015108)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0085 g/L	Not Available
LogP	4.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	4.14	ALOGPS
logP	4.56	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.86 m³·mol⁻¹	ChemAxon
Polarizability	41.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	201.691	30932474
DeepCCS	[M-H]-	199.295	30932474
DeepCCS	[M-2H]-	232.18	30932474
DeepCCS	[M+Na]+	207.604	30932474
AllCCS	[M+H]+	200.0	32859911
AllCCS	[M+H-H2O]+	197.4	32859911
AllCCS	[M+NH4]+	202.5	32859911
AllCCS	[M+Na]+	203.2	32859911
AllCCS	[M-H]-	197.4	32859911
AllCCS	[M+Na-2H]-	197.3	32859911
AllCCS	[M+HCOO]-	197.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ezetimibe	O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1	4664.1	Standard polar	33892256
Ezetimibe	O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1	3142.2	Standard non polar	33892256
Ezetimibe	O[C@@H](CC[C@@H]1[C@H](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1	3367.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ezetimibe,1TMS,isomer #1	C[Si](C)(C)O[C@@H](CC[C@H]1C(=O)N(C2=CC=C(F)C=C2)[C@@H]1C1=CC=C(O)C=C1)C1=CC=C(F)C=C1	3152.0	Semi standard non polar	33892256
Ezetimibe,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@@H]2[C@@H](CC[C@H](O)C3=CC=C(F)C=C3)C(=O)N2C2=CC=C(F)C=C2)C=C1	3183.5	Semi standard non polar	33892256
Ezetimibe,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2[C@@H](CC[C@H](O[Si](C)(C)C)C3=CC=C(F)C=C3)C(=O)N2C2=CC=C(F)C=C2)C=C1	3147.4	Semi standard non polar	33892256
Ezetimibe,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H](CC[C@H]1C(=O)N(C2=CC=C(F)C=C2)[C@@H]1C1=CC=C(O)C=C1)C1=CC=C(F)C=C1	3394.0	Semi standard non polar	33892256
Ezetimibe,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2[C@@H](CC[C@H](O)C3=CC=C(F)C=C3)C(=O)N2C2=CC=C(F)C=C2)C=C1	3428.6	Semi standard non polar	33892256
Ezetimibe,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2[C@@H](CC[C@H](O[Si](C)(C)C(C)(C)C)C3=CC=C(F)C=C3)C(=O)N2C2=CC=C(F)C=C2)C=C1	3590.9	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 - Ezetimibe GC-MS (Non-derivatized) - 70eV, Positive	splash10-05c6-2945000000-8a37190570bab21d1d02	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ezetimibe GC-MS (2 TMS) - 70eV, Positive	splash10-0002-1903310000-633b71d71a358012cf6a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ezetimibe GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ezetimibe GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ezetimibe LC-ESI-qTof , Positive-QTOF	splash10-0a6r-0692700000-11f020dfbb889ac85e4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ezetimibe , positive-QTOF	splash10-000i-1910000000-5b24d4adc8cd3de959fc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ezetimibe 35V, Positive-QTOF	splash10-001r-0901000000-e8fcc0996c187fba951c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ezetimibe 35V, Negative-QTOF	splash10-00di-0090000000-cd400e80926d97660b98	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 10V, Positive-QTOF	splash10-01ox-0149600000-6c8e6056b5e23340ee0e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 20V, Positive-QTOF	splash10-02i6-1794200000-9502e8a01ff6f30b9fc1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 40V, Positive-QTOF	splash10-072a-2950000000-eed640a1fd606e7a63b4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 10V, Negative-QTOF	splash10-0a4i-0122900000-b96ba99bfc7c99941d6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 20V, Negative-QTOF	splash10-0006-1921100000-e17ecfb5ab2d745ce445	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 40V, Negative-QTOF	splash10-01pa-4941000000-a0f53760eaaecdb35c3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 10V, Positive-QTOF	splash10-03di-0103900000-2a34f2e670639f066936	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 20V, Positive-QTOF	splash10-01ox-0459200000-423316cd7c679c84fecc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 40V, Positive-QTOF	splash10-03di-2944000000-431efb92dd6b4ef8117f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 10V, Negative-QTOF	splash10-0a4i-1002900000-196e25f3fee6b4c0c1b9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 20V, Negative-QTOF	splash10-0a4l-3027900000-8bcaac6304f22421df0b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ezetimibe 40V, Negative-QTOF	splash10-02tl-9742000000-4a57647def4127013cd1	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00973	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00973	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00973

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

132493

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ezetimibe

METLIN ID

Not Available

PubChem Compound

150311

PDB ID

Not Available

ChEBI ID

49040

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

Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, Graziano MP, Hughes M, Macintyre DE, Ogawa A, O'neill KA, Iyer SP, Shevell DE, Smith MM, Tang YS, Makarewicz AM, Ujjainwalla F, Altmann SW, Chapman KT, Thornberry NA: The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci U S A. 2005 Jun 7;102(23):8132-7. Epub 2005 May 31. [PubMed:15928087 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aminopeptidase N

General function:: Involved in proteolysis
Specific function:: Broad specificity aminopeptidase. Plays a role in the final digestion of peptides generated from hydrolysis of proteins by gastric and pancreatic proteases. May play a critical role in the pathogenesis of cholesterol gallstone disease. May be involved in the metabolism of regulatory peptides of diverse cell types, responsible for the processing of peptide hormones, such as angiotensin III and IV, neuropeptides, and chemokines. Found to cleave antigen peptides bound to major histocompatibility complex class II molecules of presenting cells and to degrade neurotransmitters at synaptic junctions. Is also implicated as a regulator of IL-8 bioavailability in the endometrium, and therefore may contribute to the regulation of angiogenesis. Is used as a marker for acute myeloid leukemia and plays a role in tumor invasion. In case of human coronavirus 229E (HCoV-229E) infection, serves as receptor for HCoV-229E spike glycoprotein. Mediates as well human cytomegalovirus (HCMV) infection.
Gene Name:: ANPEP
Uniprot ID:: P15144
Molecular weight:: Not Available

References

Kramer W, Girbig F, Corsiero D, Pfenninger A, Frick W, Jahne G, Rhein M, Wendler W, Lottspeich F, Hochleitner EO, Orso E, Schmitz G: Aminopeptidase N (CD13) is a molecular target of the cholesterol absorption inhibitor ezetimibe in the enterocyte brush border membrane. J Biol Chem. 2005 Jan 14;280(2):1306-20. Epub 2004 Oct 19. [PubMed:15494415 ]

Enzyme Details

2. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

References

Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20. [PubMed:14977865 ]
Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]

Enzyme Details

3. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

References

Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20. [PubMed:14977865 ]
Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]

Enzyme Details

5. UDP-glucuronosyltransferase 1-3

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

References

Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]

Enzyme Details

6. Sterol O-acyltransferase 1

General function:: Involved in acyl-CoA binding
Specific function:: Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:: SOAT1
Uniprot ID:: P35610
Molecular weight:: 58130.665

References

Singh A, Basit A, Banerjee UC: Burkholderia cenocepacia: a new biocatalyst for efficient bioreduction of ezetimibe intermediate. J Ind Microbiol Biotechnol. 2009 Nov;36(11):1369-74. doi: 10.1007/s10295-009-0622-z. Epub 2009 Aug 8. [PubMed:19669185 ]
Costet P: Molecular pathways and agents for lowering LDL-cholesterol in addition to statins. Pharmacol Ther. 2010 Jun;126(3):263-78. doi: 10.1016/j.pharmthera.2010.02.006. Epub 2010 Mar 19. [PubMed:20227438 ]
Wang HH, Portincasa P, Mendez-Sanchez N, Uribe M, Wang DQ: Effect of ezetimibe on the prevention and dissolution of cholesterol gallstones. Gastroenterology. 2008 Jun;134(7):2101-10. doi: 10.1053/j.gastro.2008.03.011. Epub 2008 Mar 10. [PubMed:18442485 ]

Enzyme Details

7. 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

Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]

Enzyme Details

8. Niemann-Pick C1-like protein 1

General function:: Involved in cholesterol transport
Specific function:: Play a major role in cholesterol homeostasis. Is critical for the uptake of cholesterol across the plasma membrane of the intestinal enterocyte. Is the direct molecular target of ezetimibe, a drug that inhibits cholesterol absorbtion. Lack of activity leads to multiple lipid transport defects. The protein may have a function in the transport of multiple lipids and their homeostasis, and may play a critical role in regulating lipid metabolism
Gene Name:: NPC1L1
Uniprot ID:: Q9UHC9
Molecular weight:: 148696.5

References

Altmann SW, Davis HR Jr, Zhu LJ, Yao X, Hoos LM, Tetzloff G, Iyer SP, Maguire M, Golovko A, Zeng M, Wang L, Murgolo N, Graziano MP: Niemann-Pick C1 Like 1 protein is critical for intestinal cholesterol absorption. Science. 2004 Feb 20;303(5661):1201-4. [PubMed:14976318 ]
Wang J, Williams CM, Hegele RA: Compound heterozygosity for two non-synonymous polymorphisms in NPC1L1 in a non-responder to ezetimibe. Clin Genet. 2005 Feb;67(2):175-7. [PubMed:15679830 ]
Sudhop T, Lutjohann D, von Bergmann K: Sterol transporters: targets of natural sterols and new lipid lowering drugs. Pharmacol Ther. 2005 Mar;105(3):333-41. Epub 2004 Dec 9. [PubMed:15737409 ]
Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, Graziano MP, Hughes M, Macintyre DE, Ogawa A, O'neill KA, Iyer SP, Shevell DE, Smith MM, Tang YS, Makarewicz AM, Ujjainwalla F, Altmann SW, Chapman KT, Thornberry NA: The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci U S A. 2005 Jun 7;102(23):8132-7. Epub 2005 May 31. [PubMed:15928087 ]
von Bergmann K, Sudhop T, Lutjohann D: Cholesterol and plant sterol absorption: recent insights. Am J Cardiol. 2005 Jul 4;96(1A):10D-14D. [PubMed:15992510 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]

Enzyme Details

2. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]

Enzyme Details

3. 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

Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Ezetimibe (HMDB0015108)

MOL for HMDB0015108 (Ezetimibe)

3D MOL for HMDB0015108 (Ezetimibe)

3D SDF for HMDB0015108 (Ezetimibe)

3D-SDF for HMDB0015108 (Ezetimibe)

PDB for HMDB0015108 (Ezetimibe)

3D PDB for HMDB0015108 (Ezetimibe)

SMILES for HMDB0015108 (Ezetimibe)

INCHI for HMDB0015108 (Ezetimibe)

Structure for HMDB0015108 (Ezetimibe)

3D Structure for HMDB0015108 (Ezetimibe)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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