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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015048

Secondary Accession Numbers

HMDB15048

Metabolite Identification

Common Name

Repaglinide

Description

Repaglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to cells of the pancreas to stimulate insulin release. Repaglinide induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naive to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Repaglinide is extensively metabolized in the liver and excreted in bile. Repaglinide metabolites do not possess appreciable hypoglycemic activity. Approximately 90% of a single orally administered dose is eliminated in feces and 8% in urine.

Structure

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

912
  Mrv0541 02231215062D          

 33 35  0  0  1  0            999 V2000
    5.9370   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.5246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0804   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9370   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6500    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 31  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

HMDB0015048
     RDKit          3D
Repaglinide
 69 71  0  0  0  0  0  0  0  0999 V2000
    7.0777   -0.1954    1.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6192    1.0824   -2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END

912
  Mrv0541 02231215062D          

 33 35  0  0  1  0            999 V2000
    5.9370   -0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015048

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

> <INCHI_KEY>
FAEKWTJYAYMJKF-QHCPKHFHSA-N

> <FORMULA>
C27H36N2O4

> <MOLECULAR_WEIGHT>
452.5857

> <EXACT_MASS>
452.26750765

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
51.48599953789469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

> <ALOGPS_LOGP>
5.05

> <JCHEM_LOGP>
3.946804454827218

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.519066522631515

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6754997808978898

> <JCHEM_PKA_STRONGEST_BASIC>
4.8184755016238165

> <JCHEM_POLAR_SURFACE_AREA>
78.87

> <JCHEM_REFRACTIVITY>
131.8281

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
repaglinide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015048
     RDKit          3D
Repaglinide
 69 71  0  0  0  0  0  0  0  0999 V2000
    7.0777   -0.1954    1.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -0.5007    1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6763   -0.0766   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5570   -0.2699   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764   -0.8983   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851   -1.1619   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -1.8201   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -0.9373   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799   -0.8286   -1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -0.2869    0.8614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489    0.5744    0.9446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5429    1.5316    2.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876    2.5041    2.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356    1.9664    2.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130    3.8810    1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.9741   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    2.0599   -1.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381    2.3337   -2.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    1.4898   -3.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4270    0.3926   -2.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    0.1199   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -1.0319   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -2.3176   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493   -3.4129   -0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -3.1062    0.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3746   -1.6474    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0693   -0.8138   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2108   -0.7648   -2.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.1244   -2.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496    0.1116   -2.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5491    0.7780   -2.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4672    1.1322   -3.9448 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7092    1.0304   -2.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3324   -0.9447    2.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1031    0.7953    2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8826   -0.2831    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8954   -0.1114    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264   -1.6112    1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5138   -1.2213    0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -2.1028    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -2.7584   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -0.4274    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -0.1731    1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    0.9126    3.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328    2.1194    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    2.7769    3.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931    2.8556    2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722    1.5466    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200    1.2584    3.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    4.0295    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    4.6874    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629    4.0905    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    2.7438   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    3.2327   -2.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2810    1.7149   -4.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1015   -0.2717   -2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -2.6588   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -2.3599    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698   -3.7339   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5852   -4.2976    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1976   -3.4833    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433   -3.6568    1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -1.3868    1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337   -1.4607    1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1750    0.2309    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7433   -1.0515   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -0.9471   -2.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065    0.1794   -3.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6192    1.0824   -2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  6 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 30  4  1  0
 21 16  1  0
 27 22  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  0
 29 68  1  0
 33 69  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 912                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082  -0.092   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   4.528   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   6.838   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   6.838   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.750  -4.713   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748  -2.402   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.416  -5.483   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.083  -5.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.416  -7.023   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.083  -7.023   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.750  -7.793   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082  -3.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750  -3.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.416  -2.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -5.483   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.083  -2.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416  -0.862   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -7.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -4.713   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.083  -0.862   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.750  -0.092   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748  -0.862   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415  -0.092   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.415   1.448   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.081   2.218   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.748   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.081   3.758   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.748   3.758   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.415   4.528   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415   6.068   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414   3.758   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080   4.528   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   28   32                                                       
CONECT    3   31                                                            
CONECT    4   31                                                            
CONECT    5    7    8   13                                                  
CONECT    6   12   23                                                       
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    6   14   15                                                  
CONECT   13    5   14   17                                                  
CONECT   14   12   13   18                                                  
CONECT   15   12   16                                                       
CONECT   16   15   19   20                                                  
CONECT   17   13   21                                                       
CONECT   18   14   22                                                       
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   17   22                                                       
CONECT   22   18   21                                                       
CONECT   23    1    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25   29                                                       
CONECT   28    2   26   30                                                  
CONECT   29   27   30                                                       
CONECT   30   28   29   31                                                  
CONECT   31    3    4   30                                                  
CONECT   32    2   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0015048
HETATM    1  C1  UNL     1       7.078  -0.195   1.956  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.739  -0.501   1.331  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.676  -0.077  -0.019  1.00  0.00           O  
HETATM    4  C3  UNL     1       4.557  -0.270  -0.812  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.476  -0.898  -0.239  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.285  -1.162  -0.923  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.163  -1.820  -0.208  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.042  -0.937  -0.271  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.580  -0.829  -1.415  1.00  0.00           O  
HETATM   10  N1  UNL     1      -0.529  -0.287   0.861  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.749   0.574   0.945  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.543   1.532   2.028  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.488   2.504   2.173  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.936   1.966   2.184  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.613   3.881   1.597  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.166   0.974  -0.393  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.756   2.060  -1.111  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.138   2.334  -2.406  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.983   1.490  -3.065  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.427   0.393  -2.411  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.040   0.120  -1.100  1.00  0.00           C  
HETATM   22  N2  UNL     1      -3.650  -1.032  -0.548  1.00  0.00           N  
HETATM   23  C19 UNL     1      -3.104  -2.318  -0.339  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.149  -3.413  -0.208  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.245  -3.106   0.750  1.00  0.00           C  
HETATM   26  C22 UNL     1      -5.375  -1.647   1.075  1.00  0.00           C  
HETATM   27  C23 UNL     1      -5.069  -0.814  -0.155  1.00  0.00           C  
HETATM   28  C24 UNL     1       2.211  -0.765  -2.233  1.00  0.00           C  
HETATM   29  C25 UNL     1       3.294  -0.124  -2.835  1.00  0.00           C  
HETATM   30  C26 UNL     1       4.450   0.112  -2.111  1.00  0.00           C  
HETATM   31  C27 UNL     1       5.549   0.778  -2.756  1.00  0.00           C  
HETATM   32  O3  UNL     1       5.467   1.132  -3.945  1.00  0.00           O  
HETATM   33  O4  UNL     1       6.709   1.030  -2.054  1.00  0.00           O  
HETATM   34  H1  UNL     1       7.332  -0.945   2.759  1.00  0.00           H  
HETATM   35  H2  UNL     1       7.103   0.795   2.449  1.00  0.00           H  
HETATM   36  H3  UNL     1       7.883  -0.283   1.185  1.00  0.00           H  
HETATM   37  H4  UNL     1       4.895  -0.111   1.931  1.00  0.00           H  
HETATM   38  H5  UNL     1       5.626  -1.611   1.315  1.00  0.00           H  
HETATM   39  H6  UNL     1       3.514  -1.221   0.799  1.00  0.00           H  
HETATM   40  H7  UNL     1       1.426  -2.103   0.819  1.00  0.00           H  
HETATM   41  H8  UNL     1       0.937  -2.758  -0.764  1.00  0.00           H  
HETATM   42  H9  UNL     1       0.025  -0.427   1.762  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.536  -0.173   1.270  1.00  0.00           H  
HETATM   44  H11 UNL     1      -1.562   0.913   3.011  1.00  0.00           H  
HETATM   45  H12 UNL     1      -2.533   2.119   2.195  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.569   2.777   3.341  1.00  0.00           H  
HETATM   47  H14 UNL     1       1.593   2.856   2.398  1.00  0.00           H  
HETATM   48  H15 UNL     1       1.272   1.547   1.244  1.00  0.00           H  
HETATM   49  H16 UNL     1       1.120   1.258   3.001  1.00  0.00           H  
HETATM   50  H17 UNL     1      -1.654   4.029   1.233  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.465   4.687   2.348  1.00  0.00           H  
HETATM   52  H19 UNL     1       0.163   4.091   0.825  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.078   2.744  -0.688  1.00  0.00           H  
HETATM   54  H21 UNL     1      -1.768   3.233  -2.924  1.00  0.00           H  
HETATM   55  H22 UNL     1      -3.281   1.715  -4.085  1.00  0.00           H  
HETATM   56  H23 UNL     1      -4.101  -0.272  -2.950  1.00  0.00           H  
HETATM   57  H24 UNL     1      -2.495  -2.659  -1.239  1.00  0.00           H  
HETATM   58  H25 UNL     1      -2.506  -2.360   0.578  1.00  0.00           H  
HETATM   59  H26 UNL     1      -4.470  -3.734  -1.209  1.00  0.00           H  
HETATM   60  H27 UNL     1      -3.585  -4.298   0.208  1.00  0.00           H  
HETATM   61  H28 UNL     1      -6.198  -3.483   0.286  1.00  0.00           H  
HETATM   62  H29 UNL     1      -5.143  -3.657   1.709  1.00  0.00           H  
HETATM   63  H30 UNL     1      -4.663  -1.387   1.873  1.00  0.00           H  
HETATM   64  H31 UNL     1      -6.434  -1.461   1.341  1.00  0.00           H  
HETATM   65  H32 UNL     1      -5.175   0.231   0.128  1.00  0.00           H  
HETATM   66  H33 UNL     1      -5.743  -1.052  -0.994  1.00  0.00           H  
HETATM   67  H34 UNL     1       1.298  -0.947  -2.807  1.00  0.00           H  
HETATM   68  H35 UNL     1       3.206   0.179  -3.865  1.00  0.00           H  
HETATM   69  H36 UNL     1       7.619   1.082  -2.492  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4
CONECT    4    5    5   30
CONECT    5    6   39
CONECT    6    7   28   28
CONECT    7    8   40   41
CONECT    8    9    9   10
CONECT   10   11   42
CONECT   11   12   16   43
CONECT   12   13   44   45
CONECT   13   14   15   46
CONECT   14   47   48   49
CONECT   15   50   51   52
CONECT   16   17   17   21
CONECT   17   18   53
CONECT   18   19   19   54
CONECT   19   20   55
CONECT   20   21   21   56
CONECT   21   22
CONECT   22   23   27
CONECT   23   24   57   58
CONECT   24   25   59   60
CONECT   25   26   61   62
CONECT   26   27   63   64
CONECT   27   65   66
CONECT   28   29   67
CONECT   29   30   30   68
CONECT   30   31
CONECT   31   32   32   33
CONECT   33   69
END

HMDB0015048
     RDKit          3D
Repaglinide
 69 71  0  0  0  0  0  0  0  0999 V2000
    7.0777   -0.1954    1.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -0.5007    1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6763   -0.0766   -0.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5570   -0.2699   -0.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764   -0.8983   -0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2851   -1.1619   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -1.8201   -0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417   -0.9373   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5799   -0.8286   -1.4148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5294   -0.2869    0.8614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489    0.5744    0.9446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5429    1.5316    2.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4876    2.5041    2.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356    1.9664    2.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130    3.8810    1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    0.9741   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563    2.0599   -1.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1381    2.3337   -2.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    1.4898   -3.0645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4270    0.3926   -2.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    0.1199   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -1.0319   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -2.3176   -0.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493   -3.4129   -0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -3.1062    0.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3746   -1.6474    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0693   -0.8138   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2108   -0.7648   -2.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2943   -0.1244   -2.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496    0.1116   -2.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5491    0.7780   -2.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4672    1.1322   -3.9448 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7092    1.0304   -2.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3324   -0.9447    2.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1031    0.7953    2.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8826   -0.2831    1.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8954   -0.1114    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264   -1.6112    1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5138   -1.2213    0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4256   -2.1028    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -2.7584   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -0.4274    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -0.1731    1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5620    0.9126    3.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328    2.1194    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    2.7769    3.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931    2.8556    2.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722    1.5466    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200    1.2584    3.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    4.0295    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651    4.6874    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1629    4.0905    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    2.7438   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    3.2327   -2.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2810    1.7149   -4.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1015   -0.2717   -2.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -2.6588   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -2.3599    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698   -3.7339   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5852   -4.2976    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1976   -3.4833    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433   -3.6568    1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -1.3868    1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337   -1.4607    1.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1750    0.2309    0.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7433   -1.0515   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978   -0.9471   -2.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2065    0.1794   -3.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6192    1.0824   -2.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  6 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 30  4  1  0
 21 16  1  0
 27 22  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 23 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  0
 29 68  1  0
 33 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Prandin	Kegg
Surepost	Kegg
AG-ee 388 ZW	HMDB
AG-ee 623 ZW	HMDB
Glaxo wellcome brand OF replaginide	HMDB
Novo nordisk brand 2 OF repaglinide	HMDB
Repa-glinide	HMDB
2-Ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid	HMDB
Novo nordisk brand OF repaglinide	HMDB
NovoNorm	HMDB
Repaglinide, (+-)-isomer	HMDB
2-Ethoxy-N-(alpha-(2-methyl-1-propyl)-2-piperidinobenzyl)-4-carbamoylmethylbenzoic acid	HMDB
AG-ee 388	HMDB
GlucoNorm	HMDB

Chemical Formula

C₂₇H₃₆N₂O₄

Average Molecular Weight

452.5857

Monoisotopic Molecular Weight

452.26750765

IUPAC Name

2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

Traditional Name

repaglinide

CAS Registry Number

135062-02-1

SMILES

CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O

InChI Identifier

InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

InChI Key

FAEKWTJYAYMJKF-QHCPKHFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Phenylacetamide
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
Phenol ether
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Amino acid
Tertiary amine
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:8805 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Repaglinide Action Pathway (PathBank: SMP0000454)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	130 - 131 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0029 g/L	Not Available
LogP	5.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0029 g/L	ALOGPS
logP	5.05	ALOGPS
logP	3.95	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.87 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.83 m³·mol⁻¹	ChemAxon
Polarizability	51.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	204.347	31661259
DarkChem	[M-H]-	200.698	31661259
DeepCCS	[M+H]+	209.627	30932474
DeepCCS	[M-H]-	207.232	30932474
DeepCCS	[M-2H]-	240.114	30932474
DeepCCS	[M+Na]+	215.54	30932474
AllCCS	[M+H]+	212.3	32859911
AllCCS	[M+H-H2O]+	210.3	32859911
AllCCS	[M+NH4]+	214.2	32859911
AllCCS	[M+Na]+	214.7	32859911
AllCCS	[M-H]-	206.6	32859911
AllCCS	[M+Na-2H]-	207.9	32859911
AllCCS	[M+HCOO]-	209.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Repaglinide	CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O	4320.8	Standard polar	33892256
Repaglinide	CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O	3415.3	Standard non polar	33892256
Repaglinide	CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O	3608.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Repaglinide,1TMS,isomer #1	CCOC1=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=CC=C1C(=O)O[Si](C)(C)C	3477.8	Semi standard non polar	33892256
Repaglinide,1TMS,isomer #2	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C)=CC=C1C(=O)O	3473.2	Semi standard non polar	33892256
Repaglinide,2TMS,isomer #1	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C)=CC=C1C(=O)O[Si](C)(C)C	3422.4	Semi standard non polar	33892256
Repaglinide,2TMS,isomer #1	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C)=CC=C1C(=O)O[Si](C)(C)C	3250.9	Standard non polar	33892256
Repaglinide,2TMS,isomer #1	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C)=CC=C1C(=O)O[Si](C)(C)C	4117.6	Standard polar	33892256
Repaglinide,1TBDMS,isomer #1	CCOC1=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	3702.1	Semi standard non polar	33892256
Repaglinide,1TBDMS,isomer #2	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O	3675.2	Semi standard non polar	33892256
Repaglinide,2TBDMS,isomer #1	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	3794.4	Semi standard non polar	33892256
Repaglinide,2TBDMS,isomer #1	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	3577.9	Standard non polar	33892256
Repaglinide,2TBDMS,isomer #1	CCOC1=CC(CC(=O)N([C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)[Si](C)(C)C(C)(C)C)=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	4224.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Repaglinide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g7j-2958400000-8cbddf3d4598a0fc7340	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repaglinide GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-5260910000-4aaa7a93bda9f63c45e2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repaglinide 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 - Repaglinide LC-ESI-QTOF , negative-QTOF	splash10-0udi-0000900000-c0108433e6c3f3bf1c75	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , negative-QTOF	splash10-004i-0009000000-30aa31031f07d8ae52b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , negative-QTOF	splash10-002r-0908000000-b76282b9697187110f0a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , positive-QTOF	splash10-0udi-0000900000-2f6de321d96a7df0cde9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , positive-QTOF	splash10-0udi-0140900000-4fef8b8042e88aa84955	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , positive-QTOF	splash10-001i-0290000000-4867f74dff429e78bb45	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , positive-QTOF	splash10-001i-0290000000-bdb018b622ca04e9d8b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide LC-ESI-QTOF , positive-QTOF	splash10-001i-0590000000-60f613e4ee0d364efcea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide , positive-QTOF	splash10-0f89-2791700000-333192fa8176a2febaa5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 20V, Positive-QTOF	splash10-0udi-0140900000-4fef8b8042e88aa84955	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 50V, Positive-QTOF	splash10-0089-0970000000-602d29c500b424ed363e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 20V, Negative-QTOF	splash10-004i-0009000000-30aa31031f07d8ae52b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 10V, Positive-QTOF	splash10-0udi-0000900000-dee9fb6cd200b9ec5dea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 30V, Positive-QTOF	splash10-001i-0290000000-eb9b8068f0e4a444f798	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 10V, Negative-QTOF	splash10-0udi-0000900000-c0108433e6c3f3bf1c75	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 30V, Negative-QTOF	splash10-002r-0908000000-b76282b9697187110f0a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 40V, Positive-QTOF	splash10-001i-0290000000-720a9142676a841f0079	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 20V, Positive-QTOF	splash10-0gx0-0590600000-eb3b3f1dce83738e96c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Repaglinide 10V, Positive-QTOF	splash10-0udi-0000900000-c946d573c5042841c3f6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repaglinide 10V, Positive-QTOF	splash10-0f6t-0181900000-f133163bc1e44e5ff6f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repaglinide 20V, Positive-QTOF	splash10-0002-1691100000-199236474a5fb7cb930d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repaglinide 40V, Positive-QTOF	splash10-0a5a-4940000000-4dc08f986e76785388e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repaglinide 10V, Negative-QTOF	splash10-0zfr-0010900000-dd8d5e58d8cda3e20087	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repaglinide 20V, Negative-QTOF	splash10-0bt9-1554900000-694c7b4171377cee14c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repaglinide 40V, Negative-QTOF	splash10-004i-2966000000-f2d3f7a4cbcb2910e30f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Repaglinide Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00912	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00912	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00912

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59377

KEGG Compound ID

C07670

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Repaglinide

METLIN ID

Not Available

PubChem Compound

65981

PDB ID

Not Available

ChEBI ID

348669

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

Massi-Benedetti M, Damsbo P: Pharmacology and clinical experience with repaglinide. Expert Opin Investig Drugs. 2000 Apr;9(4):885-98. [PubMed:11060717 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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 ]
Bidstrup TB, Bjornsdottir I, Sidelmann UG, Thomsen MS, Hansen KT: CYP2C8 and CYP3A4 are the principal enzymes involved in the human in vitro biotransformation of the insulin secretagogue repaglinide. Br J Clin Pharmacol. 2003 Sep;56(3):305-14. [PubMed:12919179 ]

Enzyme Details

2. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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 ]
Bidstrup TB, Bjornsdottir I, Sidelmann UG, Thomsen MS, Hansen KT: CYP2C8 and CYP3A4 are the principal enzymes involved in the human in vitro biotransformation of the insulin secretagogue repaglinide. Br J Clin Pharmacol. 2003 Sep;56(3):305-14. [PubMed:12919179 ]

Enzyme Details

3. Peroxisome proliferator-activated receptor gamma

General function:: Involved in DNA binding
Specific function:: Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:: PPARG
Uniprot ID:: P37231
Molecular weight:: 57619.6

References

Scarsi M, Podvinec M, Roth A, Hug H, Kersten S, Albrecht H, Schwede T, Meyer UA, Rucker C: Sulfonylureas and glinides exhibit peroxisome proliferator-activated receptor gamma activity: a combined virtual screening and biological assay approach. Mol Pharmacol. 2007 Feb;71(2):398-406. Epub 2006 Nov 2. [PubMed:17082235 ]

Enzyme Details

4. ATP-binding cassette sub-family C member 8

General function:: Involved in ATP binding
Specific function:: Putative subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release
Gene Name:: ABCC8
Uniprot ID:: Q09428
Molecular weight:: 177006.4

References

Hu S, Wang S, Fanelli B, Bell PA, Dunning BE, Geisse S, Schmitz R, Boettcher BR: Pancreatic beta-cell K(ATP) channel activity and membrane-binding studies with nateglinide: A comparison with sulfonylureas and repaglinide. J Pharmacol Exp Ther. 2000 May;293(2):444-52. [PubMed:10773014 ]
Sunaga Y, Gonoi T, Shibasaki T, Ichikawa K, Kusama H, Yano H, Seino S: The effects of mitiglinide (KAD-1229), a new anti-diabetic drug, on ATP-sensitive K+ channels and insulin secretion: comparison with the sulfonylureas and nateglinide. Eur J Pharmacol. 2001 Nov 9;431(1):119-25. [PubMed:11716850 ]
Hansen AM, Christensen IT, Hansen JB, Carr RD, Ashcroft FM, Wahl P: Differential interactions of nateglinide and repaglinide on the human beta-cell sulphonylurea receptor 1. Diabetes. 2002 Sep;51(9):2789-95. [PubMed:12196472 ]
Wangler B, Schneider S, Thews O, Schirrmacher E, Comagic S, Feilen P, Schwanstecher C, Schwanstecher M, Shiue CY, Alavi A, Hohnemann S, Piel M, Rosch F, Schirrmacher R: Synthesis and evaluation of (S)-2-(2-[18F]fluoroethoxy)-4-([3-methyl-1-(2-piperidin-1-yl-phenyl)-butyl-carbam oyl]-methyl)-benzoic acid ([18F]repaglinide): a promising radioligand for quantification of pancreatic beta-cell mass with positron emission tomography (PET). Nucl Med Biol. 2004 Jul;31(5):639-47. [PubMed:15219283 ]
Wangler B, Beck C, Shiue CY, Schneider S, Schwanstecher C, Schwanstecher M, Feilen PJ, Alavi A, Rosch F, Schirrmacher R: Synthesis and in vitro evaluation of (S)-2-([11C]methoxy)-4-[3-methyl-1-(2-piperidine-1-yl-phenyl)-butyl-carbamoyl]-be nzoic acid ([11C]methoxy-repaglinide): a potential beta-cell imaging agent. Bioorg Med Chem Lett. 2004 Oct 18;14(20):5205-9. [PubMed:15380228 ]
Dornhorst A: Insulinotropic meglitinide analogues. Lancet. 2001 Nov 17;358(9294):1709-16. [PubMed:11728565 ]

Showing metabocard for Repaglinide (HMDB0015048)

MOL for HMDB0015048 (Repaglinide)

3D MOL for HMDB0015048 (Repaglinide)

3D SDF for HMDB0015048 (Repaglinide)

3D-SDF for HMDB0015048 (Repaglinide)

PDB for HMDB0015048 (Repaglinide)

3D PDB for HMDB0015048 (Repaglinide)

SMILES for HMDB0015048 (Repaglinide)

INCHI for HMDB0015048 (Repaglinide)

Structure for HMDB0015048 (Repaglinide)

3D Structure for HMDB0015048 (Repaglinide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References