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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015634

Secondary Accession Numbers

HMDB15634

Metabolite Identification

Common Name

Saxagliptin

Description

Saxagliptin (rINN), previously identified as BMS-477118, is a new oral hypoglycemic (anti-diabetic drug) of the new dipeptidyl peptidase-4 (DPP-4) inhibitor class of drugs. It was developed by Bristol-Myers Squibb. A New Drug Application for saxagliptin in the treatment of type 2 diabetes was submitted to the FDA in June 2008. It was based on a drug development program with 8 randomized trials: 1 phase 2 dose-ranging (2.5 - 100 mg/d) study; 6 phase 3, 24-week controlled trials with additional controlled follow-up from 12 to 42 months, double-blinded throughout; and one 12-week mechanism-of-action trial with a 2-year follow-up period. In June 2008, it was announced that Onglyza would be the trade name under which saxagliptin will be marketed.

Structure

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

HMDB0015634
     RDKit          3D
Saxagliptin
 48 52  0  0  0  0  0  0  0  0999 V2000
    2.9234   -2.6263    2.1765 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -1.8284    1.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -0.8479    0.4480 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8556    0.5157    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583    1.2637   -0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4734    1.9596   -1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100    0.5321   -1.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7355   -0.4187   -0.5927 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633   -0.5361   -1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098    0.1758   -2.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -1.3384   -0.7920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -2.2276    0.2787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.5903   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289   -1.5921   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2907   -0.9226    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333   -0.1715   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    0.8127   -1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5778    1.8025   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    1.0549    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108    1.9369    2.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -0.0236    1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241    0.3736    0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.2205   -1.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5805   -1.0701   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    0.8767    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166    0.3971    1.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4628    1.3586   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9314    2.7000   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    2.2938   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    0.1217   -2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985   -1.9976   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6132   -3.2369    0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2978   -1.9933    1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -2.1651   -1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -2.3041    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -1.7037    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7202    0.3751   -0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178   -0.9094   -1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    1.3939   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659    2.3802    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7988    2.5125   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    1.7396    2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.6267    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691    0.3830    1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2085   -0.0582    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.1928    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    1.1478   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -0.3322   -2.6202 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 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
 19 20  1  0
 19 21  1  0
 19 22  1  0
 17 23  1  0
  8  3  1  0
 22 13  1  0
  7  5  1  0
 23 13  1  0
 21 15  1  0
  3 24  1  6
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
M  END

11243969
  Mrv0541 02241213002D          

 23 27  0  0  1  0            999 V2000
    3.0303    2.1407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3140    0.5478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6838   -0.8325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0900   -1.2595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0846   -2.3965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303    1.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7202    0.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -0.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2073   -0.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404    0.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602    0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3036   -0.4625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4987   -0.7033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8732   -1.4385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3230   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2899   -2.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1004   -0.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548   -1.6474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8197   -2.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 21  2  0  0  0  0
 17  3  1  1  0  0  0
  3 21  1  0  0  0  0
  3 22  1  0  0  0  0
 16  4  1  1  0  0  0
  5 23  3  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 16  1  0  0  0  0
  7 10  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 12  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  1  0  0  0  0
  9 15  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0015634

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m1/s1

> <INCHI_KEY>
QGJUIPDUBHWZPV-SGTAVMJGSA-N

> <FORMULA>
C18H25N3O2

> <MOLECULAR_WEIGHT>
315.41

> <EXACT_MASS>
315.194677059

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.21637212755824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
-0.07953443200000038

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.743205216079474

> <JCHEM_PKA_STRONGEST_BASIC>
7.8981657875150555

> <JCHEM_POLAR_SURFACE_AREA>
90.35

> <JCHEM_REFRACTIVITY>
83.9913

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
saxagliptin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015634
     RDKit          3D
Saxagliptin
 48 52  0  0  0  0  0  0  0  0999 V2000
    2.9234   -2.6263    2.1765 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -1.8284    1.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -0.8479    0.4480 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8556    0.5157    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583    1.2637   -0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4734    1.9596   -1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100    0.5321   -1.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7355   -0.4187   -0.5927 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633   -0.5361   -1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098    0.1758   -2.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -1.3384   -0.7920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -2.2276    0.2787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.5903   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289   -1.5921   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2907   -0.9226    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333   -0.1715   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    0.8127   -1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5778    1.8025   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    1.0549    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108    1.9369    2.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -0.0236    1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241    0.3736    0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.2205   -1.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5805   -1.0701   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    0.8767    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166    0.3971    1.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4628    1.3586   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9314    2.7000   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    2.2938   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    0.1217   -2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985   -1.9976   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6132   -3.2369    0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2978   -1.9933    1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -2.1651   -1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -2.3041    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -1.7037    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7202    0.3751   -0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178   -0.9094   -1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    1.3939   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659    2.3802    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7988    2.5125   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    1.7396    2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.6267    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691    0.3830    1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2085   -0.0582    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.1928    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    1.1478   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -0.3322   -2.6202 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 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
 19 20  1  0
 19 21  1  0
 19 22  1  0
 17 23  1  0
  8  3  1  0
 22 13  1  0
  7  5  1  0
 23 13  1  0
 21 15  1  0
  3 24  1  6
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 11243969                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       5.657   3.996   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.919   1.023   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      10.610  -1.554   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.635  -2.351   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.625  -4.473   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.944   0.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.657   2.456   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.592  -0.445   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.369   0.225   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.944   1.712   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.657  -0.241   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.987  -1.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.369   1.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.592   1.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -0.518   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.033  -0.863   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.131  -1.313   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.830  -2.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.670  -1.393   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.741  -3.774   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.521  -0.465   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.369  -3.075   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.997  -3.774   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   21                                                            
CONECT    3   17   21   22                                                  
CONECT    4   16                                                            
CONECT    5   23                                                            
CONECT    6   10   11   12   16                                             
CONECT    7    1   10   13   14                                             
CONECT    8   12   14   15                                                  
CONECT    9   11   13   15                                                  
CONECT   10    6    7                                                       
CONECT   11    6    9                                                       
CONECT   12    6    8                                                       
CONECT   13    7    9                                                       
CONECT   14    7    8                                                       
CONECT   15    8    9                                                       
CONECT   16    4    6   21                                                  
CONECT   17    3   18   19                                                  
CONECT   18   17   19   20                                                  
CONECT   19   17   18                                                       
CONECT   20   18   22                                                       
CONECT   21    2    3   16                                                  
CONECT   22    3   20   23                                                  
CONECT   23    5   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0015634
HETATM    1  N1  UNL     1       2.923  -2.626   2.177  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.186  -1.828   1.389  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.552  -0.848   0.448  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.856   0.516   1.135  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.358   1.264  -0.080  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.473   1.960  -1.013  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.710   0.532  -1.274  1.00  0.00           C  
HETATM    8  N2  UNL     1       2.736  -0.419  -0.593  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.463  -0.536  -1.172  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.210   0.176  -2.238  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.319  -1.338  -0.792  1.00  0.00           C  
HETATM   12  N3  UNL     1       0.641  -2.228   0.279  1.00  0.00           N  
HETATM   13  C9  UNL     1      -0.954  -0.590  -0.537  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.029  -1.592  -0.149  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.291  -0.923   0.331  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.833  -0.172  -0.873  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.813   0.813  -1.301  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.578   1.802  -0.184  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.025   1.055   1.010  1.00  0.00           C  
HETATM   20  O2  UNL     1      -1.711   1.937   2.037  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.965  -0.024   1.479  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.724   0.374   0.603  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.467   0.220  -1.683  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.581  -1.070  -0.023  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.884   0.877   1.489  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.617   0.397   1.909  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.463   1.359  -0.111  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.931   2.700  -1.678  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.496   2.294  -0.609  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.331   0.122  -2.056  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.099  -1.998  -1.679  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.613  -3.237   0.029  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.298  -1.993   1.210  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.252  -2.165  -1.096  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.597  -2.304   0.551  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.972  -1.704   0.679  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.720   0.375  -0.530  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.118  -0.909  -1.633  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.237   1.394  -2.167  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.466   2.380   0.079  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.799   2.513  -0.518  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.312   1.740   2.807  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.416  -0.627   2.231  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.869   0.383   1.982  1.00  0.00           H  
HETATM   45  H22 UNL     1      -0.208  -0.058   1.454  1.00  0.00           H  
HETATM   46  H23 UNL     1      -0.058   1.193   0.202  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.818   1.148  -1.751  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.506  -0.332  -2.620  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    8   24
CONECT    4    5   25   26
CONECT    5    6    7   27
CONECT    6    7   28   29
CONECT    7    8   30
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   13   31
CONECT   12   32   33
CONECT   13   14   22   23
CONECT   14   15   34   35
CONECT   15   16   21   36
CONECT   16   17   37   38
CONECT   17   18   23   39
CONECT   18   19   40   41
CONECT   19   20   21   22
CONECT   20   42
CONECT   21   43   44
CONECT   22   45   46
CONECT   23   47   48
END

HMDB0015634
     RDKit          3D
Saxagliptin
 48 52  0  0  0  0  0  0  0  0999 V2000
    2.9234   -2.6263    2.1765 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856   -1.8284    1.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -0.8479    0.4480 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8556    0.5157    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3583    1.2637   -0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4734    1.9596   -1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100    0.5321   -1.2741 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7355   -0.4187   -0.5927 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4633   -0.5361   -1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2098    0.1758   -2.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -1.3384   -0.7920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -2.2276    0.2787 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.5903   -0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289   -1.5921   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2907   -0.9226    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8333   -0.1715   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    0.8127   -1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5778    1.8025   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    1.0549    1.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7108    1.9369    2.0373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -0.0236    1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7241    0.3736    0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4666    0.2205   -1.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5805   -1.0701   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    0.8767    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166    0.3971    1.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4628    1.3586   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9314    2.7000   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4957    2.2938   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    0.1217   -2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0985   -1.9976   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6132   -3.2369    0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2978   -1.9933    1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -2.1651   -1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -2.3041    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9720   -1.7037    0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7202    0.3751   -0.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1178   -0.9094   -1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2371    1.3939   -2.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659    2.3802    0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7988    2.5125   -0.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3122    1.7396    2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.6267    2.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691    0.3830    1.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2085   -0.0582    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0585    1.1928    0.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181    1.1478   -1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062   -0.3322   -2.6202 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 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
 19 20  1  0
 19 21  1  0
 19 22  1  0
 17 23  1  0
  8  3  1  0
 22 13  1  0
  7  5  1  0
 23 13  1  0
 21 15  1  0
  3 24  1  6
  4 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  6 29  1  0
  7 30  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1S,3S,5S)-2-((2S)-Amino(3-hydroxytricyclo(3.3.1.13,7)dec-1-yl)acetyl)-2-azabicyclo(3.1.0)hexane-3-carbonitrile	ChEBI
BMS 477118	ChEBI
BMS-477118	ChEBI
Onglyza	HMDB
3-Hydroxyadamantylglycine-4,5-methanoprolinenitrile hydrate	HMDB

Chemical Formula

C₁₈H₂₅N₃O₂

Average Molecular Weight

315.41

Monoisotopic Molecular Weight

315.194677059

IUPAC Name

(1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Traditional Name

saxagliptin

CAS Registry Number

361442-04-8

SMILES

N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2

InChI Identifier

InChI=1S/C18H25N3O2/c19-8-13-2-12-3-14(12)21(13)16(22)15(20)17-4-10-1-11(5-17)7-18(23,6-10)9-17/h10-15,23H,1-7,9,20H2/t10?,11?,12-,13+,14+,15-,17?,18?/m1/s1

InChI Key

QGJUIPDUBHWZPV-SGTAVMJGSA-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-acyl-piperidine
N-acylpyrrolidine
Piperidine
Cyclic alcohol
Pyrrolidine
Tertiary carboxylic acid amide
Tertiary alcohol
Carboxamide group
Carbonitrile
Nitrile
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Primary amine
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:71272 )
azabicycloalkane (CHEBI:71272 )
monocarboxylic acid amide (CHEBI:71272 )
adamantanes (CHEBI:71272 )
nitrile (CHEBI:71272 )

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

Extracellular (HMDB: HMDB0015634)
Membrane (HMDB: HMDB0015634)

Source

Exogenous

Exogenous (HMDB: HMDB0015634)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.26 g/L	ALOGPS
logP	0.88	ALOGPS
logP	-0.08	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	14.74	ChemAxon
pKa (Strongest Basic)	7.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.99 m³·mol⁻¹	ChemAxon
Polarizability	34.22 Å³	ChemAxon
Number of Rings	5	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]+	174.855	31661259
DarkChem	[M-H]-	172.066	31661259
DeepCCS	[M-2H]-	201.138	30932474
DeepCCS	[M+Na]+	175.956	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	173.2	32859911
AllCCS	[M+NH4]+	178.4	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	178.2	32859911
AllCCS	[M+HCOO]-	177.8	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.	2.45 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9746 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	246.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1400.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	187.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	148.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.9 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	349.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	548.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	748.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	282.1 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	1017.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	501.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.3 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	407.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Saxagliptin	N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2	2517.0	Standard polar	33892256
Saxagliptin	N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2	2787.1	Standard non polar	33892256
Saxagliptin	N[C@H](C(=O)N1[C@H]2C[C@H]2C[C@H]1C#N)C12CC3CC(CC(O)(C3)C1)C2	2941.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Saxagliptin,1TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC([C@H](N)C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)(C3)C2	2593.1	Semi standard non polar	33892256
Saxagliptin,1TMS,isomer #2	C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2	2678.3	Semi standard non polar	33892256
Saxagliptin,2TMS,isomer #1	C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C)(C3)C1)C2	2589.8	Semi standard non polar	33892256
Saxagliptin,2TMS,isomer #1	C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C)(C3)C1)C2	2749.1	Standard non polar	33892256
Saxagliptin,2TMS,isomer #1	C[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C)(C3)C1)C2	3801.1	Standard polar	33892256
Saxagliptin,2TMS,isomer #2	C[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C	2808.3	Semi standard non polar	33892256
Saxagliptin,2TMS,isomer #2	C[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C	2939.4	Standard non polar	33892256
Saxagliptin,2TMS,isomer #2	C[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C	3827.8	Standard polar	33892256
Saxagliptin,3TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	2740.2	Semi standard non polar	33892256
Saxagliptin,3TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	2843.1	Standard non polar	33892256
Saxagliptin,3TMS,isomer #1	C[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C)[Si](C)(C)C)(C3)C2	3644.5	Standard polar	33892256
Saxagliptin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@H](N)C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)(C3)C2	2827.7	Semi standard non polar	33892256
Saxagliptin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2	2910.4	Semi standard non polar	33892256
Saxagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2	3053.3	Semi standard non polar	33892256
Saxagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2	3182.0	Standard non polar	33892256
Saxagliptin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O[Si](C)(C)C(C)(C)C)(C3)C1)C2	3884.2	Standard polar	33892256
Saxagliptin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C	3244.8	Semi standard non polar	33892256
Saxagliptin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C	3369.6	Standard non polar	33892256
Saxagliptin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N([C@H](C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21)C12CC3CC(CC(O)(C3)C1)C2)[Si](C)(C)C(C)(C)C	3933.2	Standard polar	33892256
Saxagliptin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	3423.6	Semi standard non polar	33892256
Saxagliptin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	3405.0	Standard non polar	33892256
Saxagliptin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC12CC3CC(C1)CC([C@@H](C(=O)N1[C@H](C#N)C[C@@H]4C[C@@H]41)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)(C3)C2	3754.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Saxagliptin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-9810000000-9ea6dee5e5df7feeccf4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Saxagliptin GC-MS (1 TMS) - 70eV, Positive	splash10-0w2i-9640000000-edbf7dd75a87c2e60523	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Saxagliptin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Saxagliptin 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 - Saxagliptin 10V, Positive-QTOF	splash10-00kb-0595000000-b2310ee91b2c4452305f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Positive-QTOF	splash10-03e9-1920000000-c732c7118b29d97a0034	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Positive-QTOF	splash10-03di-2900000000-e667b1c85a4362bf4439	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Negative-QTOF	splash10-03di-0029000000-d07ae8c4becc497aefbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Negative-QTOF	splash10-0bta-1954000000-e69611219b56c95d4fcc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Negative-QTOF	splash10-0a4l-8900000000-c3f60d50781702a5ee87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Positive-QTOF	splash10-014i-0319000000-80878b9b214b58a1e91b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Positive-QTOF	splash10-001l-1911000000-f644cfc5788567bebc0d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Positive-QTOF	splash10-01q9-2900000000-6de6bc70428ab68d2960	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 10V, Negative-QTOF	splash10-03di-0009000000-08c714e7a3cf3391b9ca	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 20V, Negative-QTOF	splash10-08fr-1937000000-046e1094e71a80b7a9b3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Saxagliptin 40V, Negative-QTOF	splash10-0bt9-4933000000-87784043f4db6b4397a2	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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 DB06335	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06335	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06335

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9419005

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Saxagliptin

METLIN ID

Not Available

PubChem Compound

11243969

PDB ID

Not Available

ChEBI ID

71272

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

Barnett A: DPP-4 inhibitors and their potential role in the management of type 2 diabetes. Int J Clin Pract. 2006 Nov;60(11):1454-70. [PubMed:17073841 ]
Crepaldi G, Carruba M, Comaschi M, Del Prato S, Frajese G, Paolisso G: Dipeptidyl peptidase 4 (DPP-4) inhibitors and their role in Type 2 diabetes management. J Endocrinol Invest. 2007 Jul-Aug;30(7):610-4. [PubMed:17848846 ]
Metzler WJ, Yanchunas J, Weigelt C, Kish K, Klei HE, Xie D, Zhang Y, Corbett M, Tamura JK, He B, Hamann LG, Kirby MS, Marcinkeviciene J: Involvement of DPP-IV catalytic residues in enzyme-saxagliptin complex formation. Protein Sci. 2008 Feb;17(2):240-50. doi: 10.1110/ps.073253208. [PubMed:18227430 ]
Rosenstock J, Sankoh S, List JF: Glucose-lowering activity of the dipeptidyl peptidase-4 inhibitor saxagliptin in drug-naive patients with type 2 diabetes. Diabetes Obes Metab. 2008 May;10(5):376-86. doi: 10.1111/j.1463-1326.2008.00876.x. Epub 2008 Mar 18. [PubMed:18355324 ]
Golightly LK, Drayna CC, McDermott MT: Comparative clinical pharmacokinetics of dipeptidyl peptidase-4 inhibitors. Clin Pharmacokinet. 2012 Aug 1;51(8):501-14. doi: 10.2165/11632930-000000000-00000. [PubMed:22686547 ]
Ali S, Fonseca V: Saxagliptin overview: special focus on safety and adverse effects. Expert Opin Drug Saf. 2013 Jan;12(1):103-9. doi: 10.1517/14740338.2013.741584. Epub 2012 Nov 9. [PubMed:23137182 ]
Russell S: Incretin-based therapies for type 2 diabetes mellitus: a review of direct comparisons of efficacy, safety and patient satisfaction. Int J Clin Pharm. 2013 Apr;35(2):159-72. doi: 10.1007/s11096-012-9729-9. Epub 2012 Dec 22. [PubMed:23263796 ]

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

Upreti VV, Boulton DW, Li L, Ching A, Su H, Lacreta FP, Patel CG: Effect of rifampicin on the pharmacokinetics and pharmacodynamics of saxagliptin, a dipeptidyl peptidase-4 inhibitor, in healthy subjects. Br J Clin Pharmacol. 2011 Jul;72(1):92-102. doi: 10.1111/j.1365-2125.2011.03937.x. [PubMed:21651615 ]
Patel CG, Kornhauser D, Vachharajani N, Komoroski B, Brenner E, Handschuh del Corral M, Li L, Boulton DW: Saxagliptin, a potent, selective inhibitor of DPP-4, does not alter the pharmacokinetics of three oral antidiabetic drugs (metformin, glyburide or pioglitazone) in healthy subjects. Diabetes Obes Metab. 2011 Jul;13(7):604-14. doi: 10.1111/j.1463-1326.2011.01381.x. [PubMed:21332626 ]
Scheen AJ: Dipeptidylpeptidase-4 inhibitors (gliptins): focus on drug-drug interactions. Clin Pharmacokinet. 2010 Sep;49(9):573-88. doi: 10.2165/11532980-000000000-00000. [PubMed:20690781 ]

Enzyme Details

2. 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

References

Upreti VV, Boulton DW, Li L, Ching A, Su H, Lacreta FP, Patel CG: Effect of rifampicin on the pharmacokinetics and pharmacodynamics of saxagliptin, a dipeptidyl peptidase-4 inhibitor, in healthy subjects. Br J Clin Pharmacol. 2011 Jul;72(1):92-102. doi: 10.1111/j.1365-2125.2011.03937.x. [PubMed:21651615 ]
Patel CG, Kornhauser D, Vachharajani N, Komoroski B, Brenner E, Handschuh del Corral M, Li L, Boulton DW: Saxagliptin, a potent, selective inhibitor of DPP-4, does not alter the pharmacokinetics of three oral antidiabetic drugs (metformin, glyburide or pioglitazone) in healthy subjects. Diabetes Obes Metab. 2011 Jul;13(7):604-14. doi: 10.1111/j.1463-1326.2011.01381.x. [PubMed:21332626 ]
Scheen AJ: Dipeptidylpeptidase-4 inhibitors (gliptins): focus on drug-drug interactions. Clin Pharmacokinet. 2010 Sep;49(9):573-88. doi: 10.2165/11532980-000000000-00000. [PubMed:20690781 ]

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

Augeri DJ, Robl JA, Betebenner DA, Magnin DR, Khanna A, Robertson JG, Wang A, Simpkins LM, Taunk P, Huang Q, Han SP, Abboa-Offei B, Cap M, Xin L, Tao L, Tozzo E, Welzel GE, Egan DM, Marcinkeviciene J, Chang SY, Biller SA, Kirby MS, Parker RA, Hamann LG: Discovery and preclinical profile of Saxagliptin (BMS-477118): a highly potent, long-acting, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J Med Chem. 2005 Jul 28;48(15):5025-37. [PubMed:16033281 ]

Showing metabocard for Saxagliptin (HMDB0015634)

MOL for HMDB0015634 (Saxagliptin)

3D MOL for HMDB0015634 (Saxagliptin)

3D SDF for HMDB0015634 (Saxagliptin)

3D-SDF for HMDB0015634 (Saxagliptin)

PDB for HMDB0015634 (Saxagliptin)

3D PDB for HMDB0015634 (Saxagliptin)

SMILES for HMDB0015634 (Saxagliptin)

INCHI for HMDB0015634 (Saxagliptin)

Structure for HMDB0015634 (Saxagliptin)

3D Structure for HMDB0015634 (Saxagliptin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References