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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (5) Show 14 proteins XML

enzymes (9)transporters (5) Show 14 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014869

Secondary Accession Numbers

HMDB14869

Metabolite Identification

Common Name

Nateglinide

Description

Nateglinide 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. Nateglinide is an amino acid derivative that 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. Nateglinide is extensively metabolized in the liver and excreted in urine (83%) and feces (10%). The major metabolites possess less activity than the parent compound. One minor metabolite, the isoprene, has the same potency as its parent compound.

Structure

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

HMDB0014869
     RDKit          3D
Nateglinide
 50 51  0  0  0  0  0  0  0  0999 V2000
   -5.9200    1.6328   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3695    0.2586    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0141   -0.7489   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665    0.2930   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263   -1.0790    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -1.1471    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.2331    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977    0.2250    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.8798    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -0.4852   -0.1280 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613   -0.4862    0.1678 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3040    0.1786   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.2371   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113    1.3364   -0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483    1.4820    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5113    0.4978   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708   -0.5894   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6203   -0.7431   -1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882   -1.8842    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -2.8526    0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -2.2209    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.0659    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372    1.3368    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9851    1.7114    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176    2.3770    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8756    1.8525   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886   -0.0545    1.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7357   -1.7661   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8214   -0.5241   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1116   -0.6586   -0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    0.5463   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023   -1.6025    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.6870   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346   -1.8605   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -1.5439    1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.6886   -0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196   -1.0314   -0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674    0.1501    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -0.4746   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8407    1.1366   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    2.1008    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0623    2.3353    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667    0.6278   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6838   -1.3464   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2329   -1.6040   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -3.0775    0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811    0.4356    2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    2.0331    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281    1.5136    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    2.3022    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
  7 22  1  0
 22 23  1  0
 23  4  1  0
 18 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
M  END

 
  Mrv0541 02231214572D          
 
 23 24  0  0  1  0            999 V2000
   11.9276   -8.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9276   -9.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6439   -9.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3559   -9.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3559   -8.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6439   -7.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0652   -7.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7777   -8.3820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4903   -7.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2053   -8.3812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4893   -7.1445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7795   -9.2070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4950   -9.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4968  -10.4431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2086   -9.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7843  -10.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7862  -11.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5016  -12.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2152  -11.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2134  -10.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5016  -12.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2161  -13.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7871  -13.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0  0  0  0
  8 12  1  6  0  0  0
  6  1  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  5  7  1  0  0  0  0
 13 15  2  0  0  0  0
  1  2  2  0  0  0  0
  7  8  1  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
  3  4  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 14  1  0  0  0  0
  9 10  1  0  0  0  0
  4  5  1  0  0  0  0
  9 11  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014869

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15?,16-,17-/m1/s1

> <INCHI_KEY>
OELFLUMRDSZNSF-YJEKIOLLSA-N

> <FORMULA>
C19H27NO3

> <MOLECULAR_WEIGHT>
317.4226

> <EXACT_MASS>
317.199093735

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.574630417038684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-3-phenyl-2-{[4-(propan-2-yl)cyclohexyl]formamido}propanoic acid

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
4.028570731333334

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.278029548687222

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.997252782578585

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3783004110880809

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
89.4605

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nateglinide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014869
     RDKit          3D
Nateglinide
 50 51  0  0  0  0  0  0  0  0999 V2000
   -5.9200    1.6328   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3695    0.2586    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0141   -0.7489   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665    0.2930   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263   -1.0790    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -1.1471    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.2331    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977    0.2250    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.8798    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -0.4852   -0.1280 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613   -0.4862    0.1678 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3040    0.1786   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.2371   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113    1.3364   -0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483    1.4820    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5113    0.4978   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708   -0.5894   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6203   -0.7431   -1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882   -1.8842    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -2.8526    0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -2.2209    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.0659    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372    1.3368    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9851    1.7114    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176    2.3770    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8756    1.8525   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886   -0.0545    1.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7357   -1.7661   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8214   -0.5241   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1116   -0.6586   -0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    0.5463   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023   -1.6025    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.6870   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346   -1.8605   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -1.5439    1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.6886   -0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196   -1.0314   -0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674    0.1501    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -0.4746   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8407    1.1366   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    2.1008    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0623    2.3353    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667    0.6278   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6838   -1.3464   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2329   -1.6040   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -3.0775    0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811    0.4356    2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    2.0331    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281    1.5136    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    2.3022    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
  7 22  1  0
 22 23  1  0
 23  4  1  0
 18 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      22.265 -15.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.265 -17.194   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.602 -17.964   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.931 -17.194   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.931 -15.654   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.602 -14.884   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.255 -14.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.585 -15.646   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.915 -14.876   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      30.250 -15.645   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      28.913 -13.336   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      27.588 -17.186   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      28.924 -17.954   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.927 -19.494   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      30.256 -17.181   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      27.597 -20.260   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.601 -21.800   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.936 -22.567   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.268 -21.794   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.265 -20.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.936 -24.107   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.270 -24.877   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.603 -24.877   0.000  0.00  0.00           C+0
CONECT    1    6    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    6    7    4                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8   12    7    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   16   20                                                  
CONECT   15   13                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14                                                       
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0014869
HETATM    1  C1  UNL     1      -5.920   1.633  -0.139  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.369   0.259   0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.014  -0.749  -0.824  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.866   0.293  -0.043  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.326  -1.079   0.196  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.853  -1.147   0.391  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.240   0.233   0.348  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.198   0.225   0.640  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.620   0.880   1.622  1.00  0.00           O  
HETATM   10  N1  UNL     1       1.150  -0.485  -0.128  1.00  0.00           N  
HETATM   11  C9  UNL     1       2.561  -0.486   0.168  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.304   0.179  -0.963  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.761   0.237  -0.778  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.311   1.336  -0.112  1.00  0.00           C  
HETATM   15  C13 UNL     1       6.648   1.482   0.104  1.00  0.00           C  
HETATM   16  C14 UNL     1       7.511   0.498  -0.354  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.971  -0.589  -1.013  1.00  0.00           C  
HETATM   18  C16 UNL     1       5.620  -0.743  -1.235  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.988  -1.884   0.414  1.00  0.00           C  
HETATM   20  O2  UNL     1       2.167  -2.853   0.339  1.00  0.00           O  
HETATM   21  O3  UNL     1       4.294  -2.221   0.739  1.00  0.00           O  
HETATM   22  C18 UNL     1      -1.951   1.066   1.389  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.337   1.337   0.889  1.00  0.00           C  
HETATM   24  H1  UNL     1      -6.985   1.711   0.209  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.318   2.377   0.418  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.876   1.853  -1.236  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.589  -0.055   1.140  1.00  0.00           H  
HETATM   28  H5  UNL     1      -5.736  -1.766  -0.521  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.821  -0.524  -1.878  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.112  -0.659  -0.671  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.668   0.546  -1.123  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.902  -1.603   1.014  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.567  -1.687  -0.725  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.335  -1.861  -0.282  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.671  -1.544   1.431  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.393   0.689  -0.652  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.820  -1.031  -0.942  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.767   0.150   1.079  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.129  -0.475  -1.868  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.841   1.137  -1.197  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.631   2.101   0.244  1.00  0.00           H  
HETATM   42  H19 UNL     1       7.062   2.335   0.620  1.00  0.00           H  
HETATM   43  H20 UNL     1       8.567   0.628  -0.175  1.00  0.00           H  
HETATM   44  H21 UNL     1       7.684  -1.346  -1.361  1.00  0.00           H  
HETATM   45  H22 UNL     1       5.233  -1.604  -1.755  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.736  -3.077   0.467  1.00  0.00           H  
HETATM   47  H24 UNL     1      -1.981   0.436   2.319  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.435   2.033   1.574  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.028   1.514   1.744  1.00  0.00           H  
HETATM   50  H27 UNL     1      -3.282   2.302   0.306  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   27
CONECT    3   28   29   30
CONECT    4    5   23   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   22   36
CONECT    8    9    9   10
CONECT   10   11   37
CONECT   11   12   19   38
CONECT   12   13   39   40
CONECT   13   14   14   18
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   16   17   43
CONECT   17   18   18   44
CONECT   18   45
CONECT   19   20   20   21
CONECT   21   46
CONECT   22   23   47   48
CONECT   23   49   50
END

HMDB0014869
     RDKit          3D
Nateglinide
 50 51  0  0  0  0  0  0  0  0999 V2000
   -5.9200    1.6328   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3695    0.2586    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0141   -0.7489   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8665    0.2930   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263   -1.0790    0.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -1.1471    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    0.2331    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977    0.2250    0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203    0.8798    1.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -0.4852   -0.1280 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5613   -0.4862    0.1678 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3040    0.1786   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608    0.2371   -0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3113    1.3364   -0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483    1.4820    0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5113    0.4978   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708   -0.5894   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6203   -0.7431   -1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882   -1.8842    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -2.8526    0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -2.2209    0.7386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.0659    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372    1.3368    0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9851    1.7114    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3176    2.3770    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8756    1.8525   -1.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5886   -0.0545    1.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7357   -1.7661   -0.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8214   -0.5241   -1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1116   -0.6586   -0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    0.5463   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9023   -1.6025    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.6870   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3346   -1.8605   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -1.5439    1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930    0.6886   -0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196   -1.0314   -0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7674    0.1501    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -0.4746   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8407    1.1366   -1.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308    2.1008    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0623    2.3353    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667    0.6278   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6838   -1.3464   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2329   -1.6040   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -3.0775    0.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811    0.4356    2.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349    2.0331    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281    1.5136    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822    2.3022    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  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  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 20  2  0
 19 21  1  0
  7 22  1  0
 22 23  1  0
 23  4  1  0
 18 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
SDZ-DJN 608	HMDB

Chemical Formula

C₁₉H₂₇NO₃

Average Molecular Weight

317.4226

Monoisotopic Molecular Weight

317.199093735

IUPAC Name

(2R)-3-phenyl-2-{[4-(propan-2-yl)cyclohexyl]formamido}propanoic acid

Traditional Name

nateglinide

CAS Registry Number

105816-04-4

SMILES

CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C19H27NO3/c1-13(2)15-8-10-16(11-9-15)18(21)20-17(19(22)23)12-14-6-4-3-5-7-14/h3-7,13,15-17H,8-12H2,1-2H3,(H,20,21)(H,22,23)/t15?,16-,17-/m1/s1

InChI Key

OELFLUMRDSZNSF-YJEKIOLLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
3-phenylpropanoic-acid
Amphetamine or derivatives
Aromatic monoterpenoid
P-menthane monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014869)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Nateglinide Action Pathway (PathBank: SMP0000453)

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	2.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0085 g/L	ALOGPS
logP	3.59	ALOGPS
logP	4.03	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.46 m³·mol⁻¹	ChemAxon
Polarizability	35.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.227	31661259
DarkChem	[M-H]-	171.207	31661259
DeepCCS	[M+H]+	180.573	30932474
DeepCCS	[M-H]-	178.215	30932474
DeepCCS	[M-2H]-	212.269	30932474
DeepCCS	[M+Na]+	187.638	30932474
AllCCS	[M+H]+	179.9	32859911
AllCCS	[M+H-H2O]+	176.8	32859911
AllCCS	[M+NH4]+	182.6	32859911
AllCCS	[M+Na]+	183.4	32859911
AllCCS	[M-H]-	179.9	32859911
AllCCS	[M+Na-2H]-	180.3	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.82 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4375 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2675.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	403.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	733.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	731.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1400.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	598.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1566.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	447.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	237.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	194.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nateglinide	CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O	3357.8	Standard polar	33892256
Nateglinide	CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O	2417.9	Standard non polar	33892256
Nateglinide	CC(C)C1CC[C@@H](CC1)C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O	2525.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nateglinide,1TMS,isomer #1	CC(C)C1CCC(C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)CC1	2521.1	Semi standard non polar	33892256
Nateglinide,1TMS,isomer #2	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O)[Si](C)(C)C)CC1	2536.4	Semi standard non polar	33892256
Nateglinide,2TMS,isomer #1	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)[Si](C)(C)C)CC1	2507.8	Semi standard non polar	33892256
Nateglinide,2TMS,isomer #1	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)[Si](C)(C)C)CC1	2493.5	Standard non polar	33892256
Nateglinide,2TMS,isomer #1	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)[Si](C)(C)C)CC1	2982.7	Standard polar	33892256
Nateglinide,1TBDMS,isomer #1	CC(C)C1CCC(C(=O)N[C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)CC1	2777.6	Semi standard non polar	33892256
Nateglinide,1TBDMS,isomer #2	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O)[Si](C)(C)C(C)(C)C)CC1	2776.5	Semi standard non polar	33892256
Nateglinide,2TBDMS,isomer #1	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1	2975.4	Semi standard non polar	33892256
Nateglinide,2TBDMS,isomer #1	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1	2869.7	Standard non polar	33892256
Nateglinide,2TBDMS,isomer #1	CC(C)C1CCC(C(=O)N([C@H](CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1	3187.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nateglinide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9520000000-a244c6c35af375e20dc4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nateglinide GC-MS (1 TMS) - 70eV, Positive	splash10-00fs-9433000000-53bbea10b7e37a78956e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nateglinide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 10V, Positive-QTOF	splash10-014i-3449000000-50b24d9b3ac051164f7d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 20V, Positive-QTOF	splash10-0uk9-4931000000-d475a1738fae856ab419	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 40V, Positive-QTOF	splash10-0006-9200000000-2c0c4efc63c909e7557d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 10V, Negative-QTOF	splash10-014i-0259000000-7e7280ea8842be0f9884	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 20V, Negative-QTOF	splash10-01di-1983000000-b31e6d0fa00dc39b50ca	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 40V, Negative-QTOF	splash10-002f-7900000000-064b989d9bbdfcb88a70	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 10V, Positive-QTOF	splash10-014i-0609000000-01318b228a87e2d79f7d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 20V, Positive-QTOF	splash10-00di-1901000000-27902453d74dd204976f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 40V, Positive-QTOF	splash10-00o3-7910000000-9bc2d3a8e45f893d9dd2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 10V, Negative-QTOF	splash10-014i-0009000000-f61e4684d2f91b1d10d6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 20V, Negative-QTOF	splash10-014i-1619000000-6755e98673286ffac6cc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nateglinide 40V, Negative-QTOF	splash10-01ox-6910000000-2563c0d847d59d5e8424	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Nateglinide Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00731	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00731	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26329508

KEGG Compound ID

C12508

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nateglinide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

146727

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-9

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 has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

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 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

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 ]

Enzyme Details

3. 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 ]

Enzyme Details

4. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2D6

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

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

7. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

8. 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

9. 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 ]
Chachin M, Yamada M, Fujita A, Matsuoka T, Matsushita K, Kurachi Y: Nateglinide, a D-phenylalanine derivative lacking either a sulfonylurea or benzamido moiety, specifically inhibits pancreatic beta-cell-type K(ATP) channels. J Pharmacol Exp Ther. 2003 Mar;304(3):1025-32. [PubMed:12604678 ]
Norman P, Rabasseda X: Nateglinide: A structurally novel, short-acting, hypoglycemic agent. Drugs Today (Barc). 2001 Jun;37(6):411-426. [PubMed:12764427 ]
Dornhorst A: Insulinotropic meglitinide analogues. Lancet. 2001 Nov 17;358(9294):1709-16. [PubMed:11728565 ]

Transporters

Enzyme Details

1. Monocarboxylate transporter 1

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:: SLC16A1
Uniprot ID:: P53985
Molecular weight:: 53957.7

References

Okamura A, Emoto A, Koyabu N, Ohtani H, Sawada Y: Transport and uptake of nateglinide in Caco-2 cells and its inhibitory effect on human monocarboxylate transporter MCT1. Br J Pharmacol. 2002 Oct;137(3):391-9. [PubMed:12237260 ]

Enzyme Details

2. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Terada T, Sawada K, Saito H, Hashimoto Y, Inui K: Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2. Eur J Pharmacol. 2000 Mar 24;392(1-2):11-7. [PubMed:10748266 ]

Enzyme Details

3. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Terada T, Sawada K, Saito H, Hashimoto Y, Inui K: Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2. Eur J Pharmacol. 2000 Mar 24;392(1-2):11-7. [PubMed:10748266 ]

Enzyme Details

4. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Uchida Y, Kamiie J, Ohtsuki S, Terasaki T: Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharm Res. 2007 Dec;24(12):2281-96. Epub 2007 Oct 16. [PubMed:17939016 ]

Enzyme Details

5. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Uwai Y, Saito H, Hashimoto Y, Inui K: Inhibitory effect of anti-diabetic agents on rat organic anion transporter rOAT1. Eur J Pharmacol. 2000 Jun 16;398(2):193-7. [PubMed:10854830 ]

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

Show all enzymes and transporters

Showing metabocard for Nateglinide (HMDB0014869)

MOL for HMDB0014869 (Nateglinide)

3D MOL for HMDB0014869 (Nateglinide)

3D SDF for HMDB0014869 (Nateglinide)

3D-SDF for HMDB0014869 (Nateglinide)

PDB for HMDB0014869 (Nateglinide)

3D PDB for HMDB0014869 (Nateglinide)

SMILES for HMDB0014869 (Nateglinide)

INCHI for HMDB0014869 (Nateglinide)

Structure for HMDB0014869 (Nateglinide)

3D Structure for HMDB0014869 (Nateglinide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References

References

References

References

References