Chemical Components in the PDB

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715 : Summary

Code

715

One-letter code

X

Molecule name

(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-A MINE

Synonyms

Sitagliptin

Systematic names

ProgramVersionName
ACDLabs 10.04 (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
OpenEye OEToolkits 1.5.0 (3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[3,4-c]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one

Formula

C16 H15 F6 N5 O

Formal charge

0

Molecular weight

407.314 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 10.04 Fc1cc(c(F)cc1F)CC(N)CC(=O)N3Cc2nnc(n2CC3)C(F)(F)F
SMILES CACTVS 3.341 N[CH](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)Cc3cc(F)c(F)cc3F
SMILES OpenEye OEToolkits 1.5.0 c1c(c(cc(c1F)F)F)CC(CC(=O)N2CCn3c(nnc3C(F)(F)F)C2)N
Canonical SMILES CACTVS 3.341 N[C@@H](CC(=O)N1CCn2c(C1)nnc2C(F)(F)F)Cc3cc(F)c(F)cc3F
Canonical SMILES OpenEye OEToolkits 1.5.0 c1c(c(cc(c1F)F)F)C[C@H](CC(=O)N2CCn3c(nnc3C(F)(F)F)C2)N

IUPAC InChI

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

IUPAC InChI key

MFFMDFFZMYYVKS-SECBINFHSA-N
715

wwPDB Information

Atom count

43 (28 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2004-08-16

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



715 : Atoms of Molecule

Total Number of Atoms: 43
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C1 C C1 N Y N 0 1.658 0.142 5.977
2 C2 C C2 N Y N 0 1.392 -0.375 4.72
3 C3 C C3 N Y N 0 0.093 -0.695 4.364
4 C4 C C4 N Y N 0 -0.937 -0.509 5.266
5 C5 C C5 N Y N 0 -0.672 0.002 6.524
6 C6 C C6 N Y N 0 0.627 0.328 6.88
7 F9 F F9 N N N 0 -1.68 0.183 7.406
8 F10 F F10 N N N 0 2.399 -0.557 3.838
9 C11 C C11 N N N 0 -0.195 -1.253 2.994
10 C12 C C12 R N N 0 -0.492 -0.104 2.028
11 C15 C C15 N N N 0 -0.785 -0.67 0.638
12 C16 C C16 N N N 0 -1.077 0.461 -0.313
13 N19 N N19 N N N 0 -1.366 0.199 -1.603
14 N20 N N20 N N N 0 0.672 0.788 1.958
15 O22 O O22 N N N 0 -1.053 1.608 0.082
16 C25 C C25 N N N 0 -1.654 1.288 -2.55
17 C26 C C26 N N N 0 -0.578 1.306 -3.642
18 N27 N N27 N Y N 0 -0.347 -0.059 -4.111
19 C28 C C28 N Y N 0 -0.698 -1.187 -3.443
20 C29 C C29 N N N 0 -1.395 -1.186 -2.108
21 C39 C C39 N Y N 0 0.239 -0.468 -5.254
22 N40 N N40 N Y N 0 0.233 -1.776 -5.244
23 N41 N N41 N Y N 0 -0.325 -2.2 -4.162
24 C42 C C42 N N N 0 0.797 0.415 -6.339
25 F43 F F43 N N N 0 1.324 -0.378 -7.363
26 F44 F F44 N N N 0 -0.222 1.223 -6.854
27 F45 F F45 N N N 0 1.809 1.223 -5.809
28 F46 F F46 N N N 0 0.886 0.827 8.108
29 H1 H H1 N N N 0 2.671 0.396 6.253
30 H4 H H4 N N N 0 -1.949 -0.763 4.989
31 H111 H 1H11 N N N 0 -1.059 -1.915 3.047
32 H112 H 2H11 N N N 0 0.67 -1.812 2.639
33 H12 H H12 N N N 0 -1.357 0.455 2.383
34 H151 H 1H15 N N N 0 0.079 -1.229 0.283
35 H152 H 2H15 N N N 0 -1.649 -1.332 0.69
36 H201 H 1H20 N N N 0 1.445 0.231 1.626
37 H202 H 2H20 N N N 0 0.474 1.467 1.238
38 H251 H 1H25 N N N 0 -2.631 1.126 -3.004
39 H252 H 2H25 N N N 0 -1.651 2.241 -2.021
40 H261 H 1H26 N N N 0 -0.914 1.925 -4.474
41 H262 H 2H26 N N N 0 0.347 1.712 -3.235
42 H291 H 1H29 N N N 0 -0.875 -1.848 -1.416
43 H292 H 2H29 N N N 0 -2.429 -1.509 -2.228



715 : Chemical Bonds

Total Number of Bonds: 45
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C1 C2 C C doub 1.38 N Y
2 C1 C6 C C sing 1.38 N Y
3 C1 H1 C H sing 1.08 N N
4 C2 C3 C C sing 1.38 N Y
5 C2 F10 C F sing 1.35 N N
6 C3 C4 C C doub 1.38 N Y
7 C3 C11 C C sing 1.51 N N
8 C4 C5 C C sing 1.38 N Y
9 C4 H4 C H sing 1.08 N N
10 C5 C6 C C doub 1.39 N Y
11 C5 F9 C F sing 1.35 N N
12 C6 F46 C F sing 1.35 N N
13 C11 C12 C C sing 1.53 N N
14 C11 H111 C H sing 1.09 N N
15 C11 H112 C H sing 1.09 N N
16 C12 C15 C C sing 1.53 N N
17 C12 N20 C N sing 1.47 N N
18 C12 H12 C H sing 1.09 N N
19 C15 C16 C C sing 1.51 N N
20 C15 H151 C H sing 1.09 N N
21 C15 H152 C H sing 1.09 N N
22 C16 N19 C N sing 1.35 N N
23 C16 O22 C O doub 1.21 N N
24 N19 C25 N C sing 1.47 N N
25 N19 C29 N C sing 1.47 N N
26 N20 H201 N H sing 1.01 N N
27 N20 H202 N H sing 1.01 N N
28 C25 C26 C C sing 1.53 N N
29 C25 H251 C H sing 1.09 N N
30 C25 H252 C H sing 1.09 N N
31 C26 N27 C N sing 1.46 N N
32 C26 H261 C H sing 1.09 N N
33 C26 H262 C H sing 1.09 N N
34 N27 C28 N C sing 1.36 N Y
35 N27 C39 N C sing 1.35 N Y
36 C28 C29 C C sing 1.51 N N
37 C28 N41 C N doub 1.3 N Y
38 C29 H291 C H sing 1.09 N N
39 C29 H292 C H sing 1.09 N N
40 C39 N40 C N doub 1.31 N Y
41 C39 C42 C C sing 1.51 N N
42 N40 N41 N N sing 1.29 N Y
43 C42 F43 C F sing 1.4 N N
44 C42 F44 C F sing 1.4 N N
45 C42 F45 C F sing 1.4 N N



715 : Used in PDB Entries

Total Number of PDB Entries: 3
Ligand Code PDB Entry ID Type Total Distinct
715 1x70 Open in New Window Bound ligand 2 1
715 4ffw Open in New Window Bound ligand 2 1
715 7y4g Open in New Window Bound ligand 3 1