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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (1) Show 4 proteins XML

enzymes (3)transporters (1) Show 4 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015390

Secondary Accession Numbers

HMDB15390

Metabolite Identification

Common Name

Sitagliptin

Description

Sitagliptin is a new oral hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. This enzyme-inhibiting drug is to be used either alone or in combination with metformin or a thiazolidinedione for control of type 2 diabetes mellitus. The drug works to competitively inhibit a protein/enzyme, dipeptidyl peptidase 4 (DPP-4), that results in an increased amount of active incretins (GLP-1 and GIP), reduced amount of release of glucagon (diminishes its release) and increased release of insulin.

Structure

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

1261
  Mrv0541 02231215212D          

 28 30  0  0  1  0            999 V2000
   10.6161    1.5194    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0882    2.5599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0476    2.0320    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.7401    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7349    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.0849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756   -0.3363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.3224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0571    0.3276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6515   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318    1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 26  1  0  0  0  0
  6 28  1  0  0  0  0
  7 19  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
  8 19  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
  9 21  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  2  0  0  0  0
 18 11  1  6  0  0  0
 12 21  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 24 27  2  0  0  0  0
 25 26  1  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0015390
     RDKit          3D
Sitagliptin
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.3704   -1.6060   -1.6504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -1.7483   -0.2997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7639   -0.9281    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -1.2413   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841   -2.0438   -1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.6150   -0.3390 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -0.8831   -1.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021   -0.5857   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131    0.7714    0.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    1.1716    0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0010    2.4495    1.1429 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    2.8131    0.9372 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8938    1.7530    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3257    1.7901    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    2.8151   -0.8674 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    0.6229   -0.4496 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0465    2.1349    1.1807 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.2913    0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.7351    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.4781    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9969   -0.4737   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7617    0.6511   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9160    0.6134   -0.9813 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4147    1.8416    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1940    2.9539    0.2318 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569    1.8445    1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562    0.7052    1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415    0.7674    2.0316 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -0.6393   -2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -2.3340   -2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5415   -2.8566   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920   -1.0337    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563    0.1684   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586   -1.9712   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -0.3083   -2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084   -0.7903   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.2877    0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7531   -0.3492    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7047    0.8651    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -2.6191    0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6262   -1.8360    1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2566   -1.4240   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737    2.7639    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 18  6  1  0
 27 20  1  0
 13  9  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 26 43  1  0
M  END

1261
  Mrv0541 02231215212D          

 28 30  0  0  1  0            999 V2000
   10.6161    1.5194    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0882    2.5599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0476    2.0320    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.7401    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.5599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7349    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.0849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756   -0.3363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.3224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0571    0.3276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4974    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6515   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5756    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8318    1.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  1  0  0  0  0
  5 26  1  0  0  0  0
  6 28  1  0  0  0  0
  7 19  2  0  0  0  0
  8 13  1  0  0  0  0
  8 15  1  0  0  0  0
  8 19  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
  9 21  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  2  0  0  0  0
 18 11  1  6  0  0  0
 12 21  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 24 27  2  0  0  0  0
 25 26  1  0  0  0  0
 26 28  2  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015390

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC(=O)N1CCN2C(C1)=NN=C2C(F)(F)F)CC1=CC(F)=C(F)C=C1F

> <INCHI_IDENTIFIER>
InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1

> <INCHI_KEY>
MFFMDFFZMYYVKS-SECBINFHSA-N

> <FORMULA>
C16H15F6N5O

> <MOLECULAR_WEIGHT>
407.3136

> <EXACT_MASS>
407.118079357

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.66431315300208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.257216275666667

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.784932056922965

> <JCHEM_POLAR_SURFACE_AREA>
77.04

> <JCHEM_REFRACTIVITY>
87.49459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sitagliptin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015390
     RDKit          3D
Sitagliptin
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.3704   -1.6060   -1.6504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -1.7483   -0.2997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7639   -0.9281    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -1.2413   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841   -2.0438   -1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.6150   -0.3390 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -0.8831   -1.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021   -0.5857   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131    0.7714    0.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    1.1716    0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0010    2.4495    1.1429 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    2.8131    0.9372 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8938    1.7530    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3257    1.7901    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    2.8151   -0.8674 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    0.6229   -0.4496 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0465    2.1349    1.1807 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.2913    0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.7351    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.4781    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9969   -0.4737   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7617    0.6511   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9160    0.6134   -0.9813 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4147    1.8416    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1940    2.9539    0.2318 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569    1.8445    1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562    0.7052    1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415    0.7674    2.0316 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -0.6393   -2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -2.3340   -2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5415   -2.8566   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920   -1.0337    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563    0.1684   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586   -1.9712   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -0.3083   -2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084   -0.7903   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.2877    0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7531   -0.3492    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7047    0.8651    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -2.6191    0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6262   -1.8360    1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2566   -1.4240   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737    2.7639    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 18  6  1  0
 27 20  1  0
 13  9  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 26 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1261                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0      19.817   2.836   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0      18.831   4.778   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0      16.889   3.793   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       5.748   1.382   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0       5.748  -4.778   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0       3.080  -3.238   0.000  0.00  0.00           F+0
HETATM    7  O   UNK     0      12.416  -2.468   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      13.750  -0.158   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      16.417   1.382   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      17.874  -0.628   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       9.748  -2.468   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      18.773   0.612   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      13.750   1.382   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.083   2.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.083  -0.928   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.417  -0.158   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082  -0.158   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -0.928   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.416  -0.928   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -0.158   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.874   1.851   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081  -0.928   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.353   3.315   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.748  -0.158   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.081  -2.468   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.748  -3.238   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414  -0.928   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -2.468   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   26                                                            
CONECT    6   28                                                            
CONECT    7   19                                                            
CONECT    8   13   15   19                                                  
CONECT    9   14   16   21                                                  
CONECT   10   12   16                                                       
CONECT   11   18                                                            
CONECT   12   10   21                                                       
CONECT   13    8   14                                                       
CONECT   14    9   13                                                       
CONECT   15    8   16                                                       
CONECT   16    9   10   15                                                  
CONECT   17   18   19                                                       
CONECT   18   11   17   20                                                  
CONECT   19    7    8   17                                                  
CONECT   20   18   22                                                       
CONECT   21    9   12   23                                                  
CONECT   22   20   24   25                                                  
CONECT   23    1    2    3   21                                             
CONECT   24    4   22   27                                                  
CONECT   25   22   26                                                       
CONECT   26    5   25   28                                                  
CONECT   27   24   28                                                       
CONECT   28    6   26   27                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0015390
HETATM    1  N1  UNL     1      -2.370  -1.606  -1.650  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.934  -1.748  -0.300  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.764  -0.928   0.111  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.456  -1.241  -0.680  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.384  -2.044  -1.619  1.00  0.00           O  
HETATM    6  N2  UNL     1       1.669  -0.615  -0.339  1.00  0.00           N  
HETATM    7  C4  UNL     1       2.879  -0.883  -1.074  1.00  0.00           C  
HETATM    8  C5  UNL     1       4.102  -0.586  -0.205  1.00  0.00           C  
HETATM    9  N3  UNL     1       4.013   0.771   0.300  1.00  0.00           N  
HETATM   10  C6  UNL     1       2.831   1.172   0.748  1.00  0.00           C  
HETATM   11  N4  UNL     1       3.001   2.450   1.143  1.00  0.00           N  
HETATM   12  N5  UNL     1       4.260   2.813   0.937  1.00  0.00           N  
HETATM   13  C7  UNL     1       4.894   1.753   0.406  1.00  0.00           C  
HETATM   14  C8  UNL     1       6.326   1.790   0.045  1.00  0.00           C  
HETATM   15  F1  UNL     1       6.485   2.815  -0.867  1.00  0.00           F  
HETATM   16  F2  UNL     1       6.810   0.623  -0.450  1.00  0.00           F  
HETATM   17  F3  UNL     1       7.047   2.135   1.181  1.00  0.00           F  
HETATM   18  C9  UNL     1       1.669   0.291   0.773  1.00  0.00           C  
HETATM   19  C10 UNL     1      -3.019  -1.735   0.713  1.00  0.00           C  
HETATM   20  C11 UNL     1      -3.805  -0.478   0.651  1.00  0.00           C  
HETATM   21  C12 UNL     1      -4.997  -0.474  -0.106  1.00  0.00           C  
HETATM   22  C13 UNL     1      -5.762   0.651  -0.231  1.00  0.00           C  
HETATM   23  F4  UNL     1      -6.916   0.613  -0.981  1.00  0.00           F  
HETATM   24  C14 UNL     1      -5.415   1.842   0.371  1.00  0.00           C  
HETATM   25  F5  UNL     1      -6.194   2.954   0.232  1.00  0.00           F  
HETATM   26  C15 UNL     1      -4.257   1.845   1.109  1.00  0.00           C  
HETATM   27  C16 UNL     1      -3.456   0.705   1.254  1.00  0.00           C  
HETATM   28  F6  UNL     1      -2.341   0.767   2.032  1.00  0.00           F  
HETATM   29  H1  UNL     1      -2.278  -0.639  -2.024  1.00  0.00           H  
HETATM   30  H2  UNL     1      -2.006  -2.334  -2.261  1.00  0.00           H  
HETATM   31  H3  UNL     1      -1.541  -2.857  -0.273  1.00  0.00           H  
HETATM   32  H4  UNL     1      -0.592  -1.034   1.189  1.00  0.00           H  
HETATM   33  H5  UNL     1      -0.956   0.168  -0.080  1.00  0.00           H  
HETATM   34  H6  UNL     1       2.859  -1.971  -1.347  1.00  0.00           H  
HETATM   35  H7  UNL     1       2.965  -0.308  -2.017  1.00  0.00           H  
HETATM   36  H8  UNL     1       5.008  -0.790  -0.764  1.00  0.00           H  
HETATM   37  H9  UNL     1       4.049  -1.288   0.654  1.00  0.00           H  
HETATM   38  H10 UNL     1       1.753  -0.349   1.713  1.00  0.00           H  
HETATM   39  H11 UNL     1       0.705   0.865   0.840  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.704  -2.619   0.608  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.626  -1.836   1.761  1.00  0.00           H  
HETATM   42  H14 UNL     1      -5.257  -1.424  -0.579  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.974   2.764   1.584  1.00  0.00           H  
CONECT    1    2   29   30
CONECT    2    3   19   31
CONECT    3    4   32   33
CONECT    4    5    5    6
CONECT    6    7   18
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   13
CONECT   10   11   11   18
CONECT   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15   16   17
CONECT   18   38   39
CONECT   19   20   40   41
CONECT   20   21   21   27
CONECT   21   22   42
CONECT   22   23   24   24
CONECT   24   25   26
CONECT   26   27   27   43
CONECT   27   28
END

HMDB0015390
     RDKit          3D
Sitagliptin
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.3704   -1.6060   -1.6504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9337   -1.7483   -0.2997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7639   -0.9281    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -1.2413   -0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841   -2.0438   -1.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.6150   -0.3390 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -0.8831   -1.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1021   -0.5857   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0131    0.7714    0.2996 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8308    1.1716    0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0010    2.4495    1.1429 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604    2.8131    0.9372 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8938    1.7530    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3257    1.7901    0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4851    2.8151   -0.8674 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    0.6229   -0.4496 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0465    2.1349    1.1807 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.2913    0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0186   -1.7351    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8055   -0.4781    0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9969   -0.4737   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7617    0.6511   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9160    0.6134   -0.9813 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4147    1.8416    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1940    2.9539    0.2318 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2569    1.8445    1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562    0.7052    1.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415    0.7674    2.0316 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2776   -0.6393   -2.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -2.3340   -2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5415   -2.8566   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920   -1.0337    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563    0.1684   -0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586   -1.9712   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   -0.3083   -2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084   -0.7903   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.2877    0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7531   -0.3492    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7047    0.8651    0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -2.6191    0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6262   -1.8360    1.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2566   -1.4240   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9737    2.7639    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 10 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 18  6  1  0
 27 20  1  0
 13  9  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  6
  3 32  1  0
  3 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 26 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R)-4-oxo-4-[3-(TRIFLUOROMETHYL)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine	ChEBI
MK-0431	ChEBI
Sitagliptina	ChEBI
Sitagliptine	ChEBI
Sitagliptinum	ChEBI
Sitagliptan	HMDB
Sitagliptin phosphate	HMDB
4-oxo-4-(3-(Trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine	HMDB
Anhydrous, sitagliptin phosphate	HMDB
Januvia	HMDB
Monohydrate, sitagliptin monophosphate	HMDB
Monohydrate, sitagliptin phosphate	HMDB
monoPhosphate monohydrate, sitagliptin	HMDB
Phosphate anhydrous, sitagliptin	HMDB
Phosphate monohydrate, sitagliptin	HMDB
Phosphate, sitagliptin	HMDB
Sitagliptin monophosphate monohydrate	HMDB
Sitagliptin phosphate anhydrous	HMDB
Sitagliptin phosphate monohydrate	HMDB

Chemical Formula

C₁₆H₁₅F₆N₅O

Average Molecular Weight

407.3136

Monoisotopic Molecular Weight

407.118079357

IUPAC Name

(3R)-3-amino-1-[3-(trifluoromethyl)-5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

Traditional Name

sitagliptin

CAS Registry Number

486460-32-6

SMILES

N[C@@H](CC(=O)N1CCN2C(C1)=NN=C2C(F)(F)F)CC1=CC(F)=C(F)C=C1F

InChI Identifier

InChI=1S/C16H15F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4,6,9H,1-3,5,7,23H2/t9-/m1/s1

InChI Key

MFFMDFFZMYYVKS-SECBINFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Amphetamine or derivatives
Triazolopyrazine
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Pyrazine
Benzenoid
1,2,4-triazole
Triazole
Tertiary carboxylic acid amide
Heteroaromatic compound
Azole
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organohalogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organofluoride
Carbonyl group
Organic oxygen compound
Amine
Organonitrogen compound
Alkyl halide
Alkyl fluoride
Hydrocarbon derivative
Organooxygen compound
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trifluorobenzene (CHEBI:40237 )
triazolopyrazine (CHEBI:40237 )

Ontology

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	0.034 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.26	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.04 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.49 m³·mol⁻¹	ChemAxon
Polarizability	32.66 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.276	30932474
DeepCCS	[M-H]-	178.88	30932474
DeepCCS	[M-2H]-	212.936	30932474
DeepCCS	[M+Na]+	187.919	30932474
AllCCS	[M+H]+	187.9	32859911
AllCCS	[M+H-H2O]+	185.3	32859911
AllCCS	[M+NH4]+	190.3	32859911
AllCCS	[M+Na]+	191.0	32859911
AllCCS	[M-H]-	185.9	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	185.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sitagliptin	N[C@@H](CC(=O)N1CCN2C(C1)=NN=C2C(F)(F)F)CC1=CC(F)=C(F)C=C1F	2637.2	Standard polar	33892256
Sitagliptin	N[C@@H](CC(=O)N1CCN2C(C1)=NN=C2C(F)(F)F)CC1=CC(F)=C(F)C=C1F	2566.4	Standard non polar	33892256
Sitagliptin	N[C@@H](CC(=O)N1CCN2C(C1)=NN=C2C(F)(F)F)CC1=CC(F)=C(F)C=C1F	2650.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sitagliptin,1TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F	2794.4	Semi standard non polar	33892256
Sitagliptin,1TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F	2689.1	Standard non polar	33892256
Sitagliptin,1TMS,isomer #1	C[Si](C)(C)N[C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F	3168.4	Standard polar	33892256
Sitagliptin,2TMS,isomer #1	C[Si](C)(C)N([C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F)[Si](C)(C)C	2943.9	Semi standard non polar	33892256
Sitagliptin,2TMS,isomer #1	C[Si](C)(C)N([C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F)[Si](C)(C)C	2830.0	Standard non polar	33892256
Sitagliptin,2TMS,isomer #1	C[Si](C)(C)N([C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F)[Si](C)(C)C	3020.6	Standard polar	33892256
Sitagliptin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F	3011.9	Semi standard non polar	33892256
Sitagliptin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F	2912.6	Standard non polar	33892256
Sitagliptin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F	3220.7	Standard polar	33892256
Sitagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F)[Si](C)(C)C(C)(C)C	3340.0	Semi standard non polar	33892256
Sitagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F)[Si](C)(C)C(C)(C)C	3256.8	Standard non polar	33892256
Sitagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([C@@H](CC(=O)N1CCN2C(=NN=C2C(F)(F)F)C1)CC1=CC(F)=C(F)C=C1F)[Si](C)(C)C(C)(C)C	3110.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sitagliptin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0295-2921000000-ee26b46d46fd47d93f77	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sitagliptin 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 - Sitagliptin LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000900000-ce9211ae5927c697618c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-QTOF , positive-QTOF	splash10-052r-0690500000-c28779e719a0e517d106	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-QTOF , positive-QTOF	splash10-0076-0930000000-1337dd7fb10ab92722b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-QTOF , positive-QTOF	splash10-00dl-0900000000-91485eb0052ad2f3637a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-QTOF , positive-QTOF	splash10-00di-0900000000-7d92431093315efaed86	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-000i-0390000000-c8853d370b51f01b194b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000900000-2895dd4a879799635ae6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-007c-0970100000-17431cd80097dff5c35f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-00dl-0910000000-29041ebd42cb7f6026df	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-00di-0900000000-dc60c3b1e5f0ba0e5e23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-0umi-0900000000-b1e1f886377c8d9b2a5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-d9e2b332d0ff3c6e283b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000900000-3403c0e74f19a7d0832a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-007c-0970000000-6aa1fc14d171d0102a2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-00dl-0910000000-62ba59074d19e0d89306	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-00di-0900000000-91600010aa7e80c0e67c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-0fmi-0900000000-d38f8b74df088a3b8232	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-08cf9f4ac284f2cd9057	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sitagliptin LC-ESI-ITFT , positive-QTOF	splash10-000i-0390000000-b6e5cd73f4ff7abd2747	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitagliptin 10V, Positive-QTOF	splash10-0a4l-0427900000-7b4c67a1a8add9744953	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitagliptin 20V, Positive-QTOF	splash10-0596-0921100000-2f2b7773685fbf5f2fab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitagliptin 40V, Positive-QTOF	splash10-0uka-3900000000-bce68660a46cc58a8e42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitagliptin 10V, Negative-QTOF	splash10-0a4i-0111900000-0b915943568998cafd46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitagliptin 20V, Negative-QTOF	splash10-0btl-0956400000-05e4d4efd040f50d1f3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitagliptin 40V, Negative-QTOF	splash10-01tc-5910000000-603304da8956f43fb6ef	2016-08-03	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	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01261	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01261	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01261

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3571948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sitagliptin

METLIN ID

Not Available

PubChem Compound

4369359

PDB ID

715

ChEBI ID

40237

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

Herman GA, Stevens C, Van Dyck K, Bergman A, Yi B, De Smet M, Snyder K, Hilliard D, Tanen M, Tanaka W, Wang AQ, Zeng W, Musson D, Winchell G, Davies MJ, Ramael S, Gottesdiener KM, Wagner JA: Pharmacokinetics and pharmacodynamics of sitagliptin, an inhibitor of dipeptidyl peptidase IV, in healthy subjects: results from two randomized, double-blind, placebo-controlled studies with single oral doses. Clin Pharmacol Ther. 2005 Dec;78(6):675-88. [PubMed:16338283 ]
Herman GA, Bergman A, Liu F, Stevens C, Wang AQ, Zeng W, Chen L, Snyder K, Hilliard D, Tanen M, Tanaka W, Meehan AG, Lasseter K, Dilzer S, Blum R, Wagner JA: Pharmacokinetics and pharmacodynamic effects of the oral DPP-4 inhibitor sitagliptin in middle-aged obese subjects. J Clin Pharmacol. 2006 Aug;46(8):876-86. [PubMed:16855072 ]
Karasik A, Aschner P, Katzeff H, Davies MJ, Stein PP: Sitagliptin, a DPP-4 inhibitor for the treatment of patients with type 2 diabetes: a review of recent clinical trials. Curr Med Res Opin. 2008 Feb;24(2):489-96. doi: 10.1185/030079908X261069 . [PubMed:18182122 ]
Pratley RE, Salsali A: Inhibition of DPP-4: a new therapeutic approach for the treatment of type 2 diabetes. Curr Med Res Opin. 2007 Apr;23(4):919-31. [PubMed:17407649 ]
Richter B, Bandeira-Echtler E, Bergerhoff K, Lerch C: Emerging role of dipeptidyl peptidase-4 inhibitors in the management of type 2 diabetes. Vasc Health Risk Manag. 2008;4(4):753-68. [PubMed:19065993 ]
Bergman A, Ebel D, Liu F, Stone J, Wang A, Zeng W, Chen L, Dilzer S, Lasseter K, Herman G, Wagner J, Krishna R: Absolute bioavailability of sitagliptin, an oral dipeptidyl peptidase-4 inhibitor, in healthy volunteers. Biopharm Drug Dispos. 2007 Sep;28(6):315-22. [PubMed:17575559 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

Scheen AJ: Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Diabetes Obes Metab. 2010 Aug;12(8):648-58. doi: 10.1111/j.1463-1326.2010.01212.x. [PubMed:20590741 ]

Enzyme Details

2. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Scheen AJ: Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Diabetes Obes Metab. 2010 Aug;12(8):648-58. doi: 10.1111/j.1463-1326.2010.01212.x. [PubMed:20590741 ]

Enzyme Details

3. 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

Herman GA, Stevens C, Van Dyck K, Bergman A, Yi B, De Smet M, Snyder K, Hilliard D, Tanen M, Tanaka W, Wang AQ, Zeng W, Musson D, Winchell G, Davies MJ, Ramael S, Gottesdiener KM, Wagner JA: Pharmacokinetics and pharmacodynamics of sitagliptin, an inhibitor of dipeptidyl peptidase IV, in healthy subjects: results from two randomized, double-blind, placebo-controlled studies with single oral doses. Clin Pharmacol Ther. 2005 Dec;78(6):675-88. [PubMed:16338283 ]
Bergman AJ, Stevens C, Zhou Y, Yi B, Laethem M, De Smet M, Snyder K, Hilliard D, Tanaka W, Zeng W, Tanen M, Wang AQ, Chen L, Winchell G, Davies MJ, Ramael S, Wagner JA, Herman GA: Pharmacokinetic and pharmacodynamic properties of multiple oral doses of sitagliptin, a dipeptidyl peptidase-IV inhibitor: a double-blind, randomized, placebo-controlled study in healthy male volunteers. Clin Ther. 2006 Jan;28(1):55-72. [PubMed:16490580 ]
Gallwitz B: Therapies for the treatment of type 2 diabetes mellitus based on incretin action. Minerva Endocrinol. 2006 Jun;31(2):133-47. [PubMed:16682937 ]
Herman GA, Bergman A, Liu F, Stevens C, Wang AQ, Zeng W, Chen L, Snyder K, Hilliard D, Tanen M, Tanaka W, Meehan AG, Lasseter K, Dilzer S, Blum R, Wagner JA: Pharmacokinetics and pharmacodynamic effects of the oral DPP-4 inhibitor sitagliptin in middle-aged obese subjects. J Clin Pharmacol. 2006 Aug;46(8):876-86. [PubMed:16855072 ]
Miller S, St Onge EL: Sitagliptin: a dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. Ann Pharmacother. 2006 Jul-Aug;40(7-8):1336-43. [PubMed:16868220 ]
Karasik A, Aschner P, Katzeff H, Davies MJ, Stein PP: Sitagliptin, a DPP-4 inhibitor for the treatment of patients with type 2 diabetes: a review of recent clinical trials. Curr Med Res Opin. 2008 Feb;24(2):489-96. doi: 10.1185/030079908X261069 . [PubMed:18182122 ]
Pratley RE, Salsali A: Inhibition of DPP-4: a new therapeutic approach for the treatment of type 2 diabetes. Curr Med Res Opin. 2007 Apr;23(4):919-31. [PubMed:17407649 ]
Lyseng-Williamson KA: Sitagliptin. Drugs. 2007;67(4):587-97. [PubMed:17352516 ]
Hermansen K, Kipnes M, Luo E, Fanurik D, Khatami H, Stein P: Efficacy and safety of the dipeptidyl peptidase-4 inhibitor, sitagliptin, in patients with type 2 diabetes mellitus inadequately controlled on glimepiride alone or on glimepiride and metformin. Diabetes Obes Metab. 2007 Sep;9(5):733-45. Epub 2007 Jun 26. [PubMed:17593236 ]
Gallwitz B: Sitagliptin: Profile of a novel DPP-4 inhibitor for the treatment of type 2 diabetes. Drugs Today (Barc). 2007 Jan;43(1):13-25. [PubMed:17315049 ]
Richter B, Bandeira-Echtler E, Bergerhoff K, Lerch C: Emerging role of dipeptidyl peptidase-4 inhibitors in the management of type 2 diabetes. Vasc Health Risk Manag. 2008;4(4):753-68. [PubMed:19065993 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

References

Scheen AJ: Pharmacokinetics of dipeptidylpeptidase-4 inhibitors. Diabetes Obes Metab. 2010 Aug;12(8):648-58. doi: 10.1111/j.1463-1326.2010.01212.x. [PubMed:20590741 ]

Showing metabocard for Sitagliptin (HMDB0015390)

MOL for HMDB0015390 (Sitagliptin)

3D MOL for HMDB0015390 (Sitagliptin)

3D SDF for HMDB0015390 (Sitagliptin)

3D-SDF for HMDB0015390 (Sitagliptin)

PDB for HMDB0015390 (Sitagliptin)

3D PDB for HMDB0015390 (Sitagliptin)

SMILES for HMDB0015390 (Sitagliptin)

INCHI for HMDB0015390 (Sitagliptin)

Structure for HMDB0015390 (Sitagliptin)

3D Structure for HMDB0015390 (Sitagliptin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References