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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015596

Secondary Accession Numbers

HMDB15596

Metabolite Identification

Common Name

Vildagliptin

Description

Vildagliptin, previously identified as LAF237, is a new oral anti-hyperglycemic agent (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. Vildagliptin inhibits the inactivation of GLP-1 and GIP by DPP-4, allowing GLP-1 and GIP to potentiate the secretion of insulin in the beta cells and suppress glucaon release by the alpha cells of the islets of Langerhans in the pancreas. It is currently in clinical trials in the U.S. and has been shown to reduce hyperglycemia in type 2 diabetes mellitus. While the drug is still not approved for use in the US, it was approved in Feb 2008 by European Medicines Agency for use within the EU and is listed on the Australian PBS with certain restrictions.

Structure

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

HMDB0015596
     RDKit          3D
Vildagliptin
 47 50  0  0  0  0  0  0  0  0999 V2000
    4.3600    2.9767   -0.9970 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286    2.1437   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339    1.0524    0.3261 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9958    0.8270    1.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058    0.0952    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -0.2235   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631   -0.1800   -0.3400 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944   -1.1505   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -2.1717   -1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -1.2379   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479   -0.1844    0.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -0.1950    0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4116    0.8114    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.8882    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4117   -0.4836    1.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1156   -1.3866    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -0.8529   -0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    0.5012   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180    1.0354   -2.3683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624    1.4212   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5427    0.3686   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -1.5454    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    1.3385    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.1620    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7687    2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2930   -0.9055    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6831    1.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.1893   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366    0.6356   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -1.2476   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -2.2556   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.3874    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871    0.5054    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    1.7928    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    1.6194    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -0.5307    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080   -0.8594    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -2.3944    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7730   -0.7246   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -1.5224   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667    0.3198   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5674    1.3727   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.4460   -0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327   -0.3033   -2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1284    1.3907   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -2.1563    0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209   -2.0678   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
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 18 20  1  0
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  7  3  1  0
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 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END


  Mrv0541 02231217582D          

 22 25  0  0  1  0            999 V2000
    4.3037   -2.5383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    1.7152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.0651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4594    1.7152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563   -0.2344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -0.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204   -1.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3405   -1.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -2.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204   -1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3405   -1.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -1.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -2.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -2.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -2.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449    0.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449    1.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2132    1.3797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5458    2.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7652    1.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3527    2.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3848    0.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 17  2  0  0  0  0
  3  6  1  0  0  0  0
  3 16  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 22  3  0  0  0  0
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  9 14  1  0  0  0  0
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 16 17  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  1  1  0  0  0
 19 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015596

> <DATABASE_NAME>
hmdb

> <SMILES>
OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N

> <INCHI_IDENTIFIER>
InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12?,13?,14-,16?,17?/m0/s1

> <INCHI_KEY>
SYOKIDBDQMKNDQ-XWTIBIIYSA-N

> <FORMULA>
C17H25N3O2

> <MOLECULAR_WEIGHT>
303.3993

> <EXACT_MASS>
303.194677059

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.1696382046072

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-{2-[(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
-0.2173945336666661

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.705235000960108

> <JCHEM_PKA_STRONGEST_BASIC>
9.03411718192587

> <JCHEM_POLAR_SURFACE_AREA>
76.36

> <JCHEM_REFRACTIVITY>
81.9991

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
EQUA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015596
     RDKit          3D
Vildagliptin
 47 50  0  0  0  0  0  0  0  0999 V2000
    4.3600    2.9767   -0.9970 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286    2.1437   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339    1.0524    0.3261 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9958    0.8270    1.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058    0.0952    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -0.2235   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631   -0.1800   -0.3400 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944   -1.1505   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -2.1717   -1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -1.2379   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479   -0.1844    0.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -0.1950    0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4116    0.8114    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.8882    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4117   -0.4836    1.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1156   -1.3866    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -0.8529   -0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    0.5012   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180    1.0354   -2.3683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624    1.4212   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5427    0.3686   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -1.5454    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    1.3385    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.1620    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7687    2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2930   -0.9055    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6831    1.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.1893   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366    0.6356   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -1.2476   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -2.2556   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.3874    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871    0.5054    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    1.7928    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    1.6194    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -0.5307    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080   -0.8594    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -2.3944    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7730   -0.7246   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -1.5224   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667    0.3198   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5674    1.3727   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.4460   -0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327   -0.3033   -2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1284    1.3907   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -2.1563    0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209   -2.0678   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 16 22  1  0
  7  3  1  0
 21 12  1  0
 22 12  1  0
 20 14  1  0
  3 23  1  1
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.034  -4.738   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.657   3.202   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.657   0.122   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.324   3.202   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.372  -0.438   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.657  -1.419   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.945  -3.649   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.369  -3.649   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.592  -4.319   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.945  -2.162   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.369  -2.162   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.592  -2.709   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.657  -4.115   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.987  -5.054   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -4.393   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.991   0.892   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.991   2.432   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.731   2.575   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.485   4.733   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.762   3.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.992   5.054   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.052   1.069   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   17                                                            
CONECT    3    6   16                                                       
CONECT    4   17   18   19                                                  
CONECT    5   22                                                            
CONECT    6    3   10   11   12                                             
CONECT    7    1   10   13   14                                             
CONECT    8   11   13   15                                                  
CONECT    9   12   14   15                                                  
CONECT   10    6    7                                                       
CONECT   11    6    8                                                       
CONECT   12    6    9                                                       
CONECT   13    7    8                                                       
CONECT   14    7    9                                                       
CONECT   15    8    9                                                       
CONECT   16    3   17                                                       
CONECT   17    2    4   16                                                  
CONECT   18    4   20   22                                                  
CONECT   19    4   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
CONECT   22    5   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0015596
HETATM    1  N1  UNL     1       4.360   2.977  -0.997  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.829   2.144  -0.424  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.134   1.052   0.326  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.996   0.827   1.583  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.206   0.095   0.988  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.818  -0.223  -0.462  1.00  0.00           C  
HETATM    7  N2  UNL     1       3.363  -0.180  -0.340  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.494  -1.151  -0.819  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.002  -2.172  -1.470  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.029  -1.238  -0.722  1.00  0.00           C  
HETATM   11  N3  UNL     1       0.448  -0.184   0.017  1.00  0.00           N  
HETATM   12  C8  UNL     1      -1.006  -0.195   0.021  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.412   0.811   1.076  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.912   0.888   1.236  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.412  -0.484   1.567  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.116  -1.387   0.394  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.682  -0.853  -0.898  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.036   0.501  -1.178  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.518   1.035  -2.368  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.462   1.421  -0.068  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.543   0.369  -1.304  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.611  -1.545   0.192  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.125   1.339   0.573  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.422   0.162   2.237  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.303   1.769   2.035  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.293  -0.905   1.496  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.125   0.683   1.052  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.196  -1.189  -0.793  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.137   0.636  -1.088  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.642  -1.248  -1.779  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.799  -2.256  -0.340  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.677  -0.387   1.058  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.987   0.505   2.055  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.005   1.793   0.759  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.123   1.619   2.024  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.504  -0.531   1.752  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.808  -0.859   2.421  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.509  -2.394   0.620  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.773  -0.725  -0.886  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.340  -1.522  -1.716  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.867   0.320  -2.964  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.567   1.373  -0.010  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.065   2.446  -0.184  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.333  -0.303  -2.148  1.00  0.00           H  
HETATM   45  H23 UNL     1      -1.128   1.391  -1.419  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.160  -2.156   0.989  1.00  0.00           H  
HETATM   47  H25 UNL     1      -1.521  -2.068  -0.807  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    7   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   30   31
CONECT   11   12   32
CONECT   12   13   21   22
CONECT   13   14   33   34
CONECT   14   15   20   35
CONECT   15   16   36   37
CONECT   16   17   22   38
CONECT   17   18   39   40
CONECT   18   19   20   21
CONECT   19   41
CONECT   20   42   43
CONECT   21   44   45
CONECT   22   46   47
END

HMDB0015596
     RDKit          3D
Vildagliptin
 47 50  0  0  0  0  0  0  0  0999 V2000
    4.3600    2.9767   -0.9970 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286    2.1437   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339    1.0524    0.3261 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9958    0.8270    1.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058    0.0952    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -0.2235   -0.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3631   -0.1800   -0.3400 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4944   -1.1505   -0.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0024   -2.1717   -1.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288   -1.2379   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479   -0.1844    0.0168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -0.1950    0.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4116    0.8114    1.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.8882    1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4117   -0.4836    1.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1156   -1.3866    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6816   -0.8529   -0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0359    0.5012   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180    1.0354   -2.3683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624    1.4212   -0.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5427    0.3686   -1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6110   -1.5454    0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1252    1.3385    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221    0.1620    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3034    1.7687    2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2930   -0.9055    1.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6831    1.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.1893   -0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1366    0.6356   -1.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423   -1.2476   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -2.2556   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6769   -0.3874    1.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9871    0.5054    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    1.7928    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233    1.6194    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -0.5307    1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080   -0.8594    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086   -2.3944    0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7730   -0.7246   -0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3398   -1.5224   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667    0.3198   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5674    1.3727   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.4460   -0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327   -0.3033   -2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1284    1.3907   -1.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -2.1563    0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209   -2.0678   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  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  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 16 22  1  0
  7  3  1  0
 21 12  1  0
 22 12  1  0
 20 14  1  0
  3 23  1  1
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
NVP-LAF237	HMDB
EQUA	HMDB
Galvus	HMDB
Jalra	HMDB
LAF 237	HMDB
LAF237	HMDB
NVP-LAF-237	HMDB
Xiliarx	HMDB
(2S)-(((3-Hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile	HMDB
NVP LAF237	MeSH
Vildagliptin	MeSH

Chemical Formula

C₁₇H₂₅N₃O₂

Average Molecular Weight

303.3993

Monoisotopic Molecular Weight

303.194677059

IUPAC Name

(2S)-1-{2-[(3-hydroxyadamantan-1-yl)amino]acetyl}pyrrolidine-2-carbonitrile

Traditional Name

EQUA

CAS Registry Number

274901-16-5

SMILES

OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N

InChI Identifier

InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12?,13?,14-,16?,17?/m0/s1

InChI Key

SYOKIDBDQMKNDQ-XWTIBIIYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
N-acylpyrrolidine
Cyclic alcohol
Pyrrolidine
Tertiary alcohol
Tertiary carboxylic acid amide
Carboxamide group
Secondary aliphatic amine
Carbonitrile
Nitrile
Secondary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015596)
Membrane (HMDB: HMDB0015596)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.75 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.75 g/L	ALOGPS
logP	1.12	ALOGPS
logP	-0.22	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	9.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82 m³·mol⁻¹	ChemAxon
Polarizability	33.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.393	31661259
DarkChem	[M-H]-	168.567	31661259
DeepCCS	[M-2H]-	204.964	30932474
DeepCCS	[M+Na]+	180.191	30932474
AllCCS	[M+H]+	172.5	32859911
AllCCS	[M+H-H2O]+	169.7	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	175.9	32859911
AllCCS	[M+HCOO]-	175.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vildagliptin	OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N	2608.3	Standard polar	33892256
Vildagliptin	OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N	2586.4	Standard non polar	33892256
Vildagliptin	OC12CC3CC(C1)CC(C3)(C2)NCC(=O)N1CCC[C@H]1C#N	2845.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vildagliptin,1TMS,isomer #1	C[Si](C)(C)OC12CC3CC(CC(NCC(=O)N4CCC[C@H]4C#N)(C3)C1)C2	2607.7	Semi standard non polar	33892256
Vildagliptin,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)N1CCC[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2	2690.6	Semi standard non polar	33892256
Vildagliptin,2TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C)(C3)C2	2650.0	Semi standard non polar	33892256
Vildagliptin,2TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C)(C3)C2	2728.8	Standard non polar	33892256
Vildagliptin,2TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C)(C3)C2	3722.5	Standard polar	33892256
Vildagliptin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(CC(NCC(=O)N4CCC[C@H]4C#N)(C3)C1)C2	2840.7	Semi standard non polar	33892256
Vildagliptin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)N1CCC[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2	2908.9	Semi standard non polar	33892256
Vildagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C(C)(C)C)(C3)C2	3099.4	Semi standard non polar	33892256
Vildagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C(C)(C)C)(C3)C2	3159.9	Standard non polar	33892256
Vildagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC(N(CC(=O)N1CCC[C@H]1C#N)[Si](C)(C)C(C)(C)C)(C3)C2	3793.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vildagliptin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9640000000-8d45705b266a6c8e72b7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vildagliptin GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-8924000000-5ae92687d7574a071316	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vildagliptin 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 - Vildagliptin LC-ESI-qTof , Positive-QTOF	splash10-0002-0049000000-467b8774aceed12b4d58	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOF	splash10-0udi-0109000000-f6f13525e0841cb9a0ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOF	splash10-0udi-0902000000-39449b9fce86086b9f42	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOF	splash10-0udi-0900000000-e42a57f8c41f08f0fe2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOF	splash10-0udi-0900000000-bdf96b3bb5758ccb2ee2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QTOF , positive-QTOF	splash10-0ue9-0900000000-813cd0c1f6616a3aac1a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOF	splash10-0udi-0309000000-4cc7261ec4a8a5eb3c50	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOF	splash10-0udi-0901000000-2828160e08a306467998	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOF	splash10-0udi-5900000000-797e5126c08d2be98d02	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOF	splash10-0f6t-9600000000-55a58d88d2018c5adff8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOF	splash10-0002-9200000000-b511fd9b2243cdaf69cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin LC-ESI-QFT , positive-QTOF	splash10-0005-9100000000-5c5cb1119f70d6852572	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin , positive-QTOF	splash10-0udi-1709000000-d62dc38a0bb019fd4bed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin 20V, Positive-QTOF	splash10-0udi-0902000000-fb003533761fa4eb101c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin 10V, Positive-QTOF	splash10-0udi-0109000000-9e22f780279800f79e8c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin 30V, Positive-QTOF	splash10-0udi-0900000000-70a44e1224e6ccd6e6cf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin 40V, Positive-QTOF	splash10-0udi-0900000000-8aee1e33231f7ccb116e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin 50V, Positive-QTOF	splash10-0ue9-0900000000-813cd0c1f6616a3aac1a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vildagliptin 10V, Positive-QTOF	splash10-0udi-0109000000-245ea3783939a252f52c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vildagliptin 10V, Positive-QTOF	splash10-0f79-1975000000-6db3cd2ad45cf37d3b43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vildagliptin 20V, Positive-QTOF	splash10-01q9-1930000000-3e7f36dc245475385bfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vildagliptin 40V, Positive-QTOF	splash10-0il0-4900000000-1ce29a450de87e7c1bec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vildagliptin 10V, Negative-QTOF	splash10-0udi-0119000000-033d575b95152dc083ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vildagliptin 20V, Negative-QTOF	splash10-0udj-9768000000-d519b4fc4f6961772f76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vildagliptin 40V, Negative-QTOF	splash10-00tg-9310000000-fa47fa8e44cd03fddfb2	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04876	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04876	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04876

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293734

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vildagliptin

METLIN ID

Not Available

PubChem Compound

6918537

PDB ID

Not Available

ChEBI ID

334541

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

Balas B, Baig MR, Watson C, Dunning BE, Ligueros-Saylan M, Wang Y, He YL, Darland C, Holst JJ, Deacon CF, Cusi K, Mari A, Foley JE, DeFronzo RA: The dipeptidyl peptidase IV inhibitor vildagliptin suppresses endogenous glucose production and enhances islet function after single-dose administration in type 2 diabetic patients. J Clin Endocrinol Metab. 2007 Apr;92(4):1249-55. Epub 2007 Jan 23. [PubMed:17244786 ]

Enzymes

Enzyme Details

1. Dipeptidyl peptidase 4

General function:: Involved in serine-type endopeptidase activity
Specific function:: Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by binding at least ADA, CAV1, IGF2R, and PTPRC. Its binding to CAV1 and CARD11 induces T-cell proliferation and NF- kappa-B activation in a T-cell receptor/CD3-dependent manner. Its interaction with ADA also regulates lymphocyte-epithelial cell adhesion. In association with FAP is involved in the pericellular proteolysis of the extracellular matrix (ECM), the migration and invasion of endothelial cells into the ECM. May be involved in the promotion of lymphatic endothelial cells adhesion, migration and tube formation. When overexpressed, enhanced cell proliferation, a process inhibited by GPC3. Acts also as a serine exopeptidase with a dipeptidyl peptidase activity that regulates various physiological processes by cleaving peptides in the circulation, including many chemokines, mitogenic growth factors, neuropeptides and peptide hormones. Removes N-terminal dipeptides sequentially from polypeptides having unsubstituted N-termini provided that the penultimate residue is proline
Gene Name:: DPP4
Uniprot ID:: P27487
Molecular weight:: 88277.9

References

Ahren B, Gomis R, Standl E, Mills D, Schweizer A: Twelve- and 52-week efficacy of the dipeptidyl peptidase IV inhibitor LAF237 in metformin-treated patients with type 2 diabetes. Diabetes Care. 2004 Dec;27(12):2874-80. [PubMed:15562200 ]
Mentlein R, Gallwitz B, Schmidt WE: Dipeptidyl-peptidase IV hydrolyses gastric inhibitory polypeptide, glucagon-like peptide-1(7-36)amide, peptide histidine methionine and is responsible for their degradation in human serum. Eur J Biochem. 1993 Jun 15;214(3):829-35. [PubMed:8100523 ]
Gupta R, Walunj SS, Tokala RK, Parsa KV, Singh SK, Pal M: Emerging drug candidates of dipeptidyl peptidase IV (DPP IV) inhibitor class for the treatment of Type 2 Diabetes. Curr Drug Targets. 2009 Jan;10(1):71-87. [PubMed:19149538 ]

Showing metabocard for Vildagliptin (HMDB0015596)

MOL for HMDB0015596 (Vildagliptin)

3D MOL for HMDB0015596 (Vildagliptin)

3D SDF for HMDB0015596 (Vildagliptin)

3D-SDF for HMDB0015596 (Vildagliptin)

PDB for HMDB0015596 (Vildagliptin)

3D PDB for HMDB0015596 (Vildagliptin)

SMILES for HMDB0015596 (Vildagliptin)

INCHI for HMDB0015596 (Vildagliptin)

Structure for HMDB0015596 (Vildagliptin)

3D Structure for HMDB0015596 (Vildagliptin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References