Chemical Components in the PDB

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21G : Summary

Code

21G

One-letter code

X

Molecule name

(2S,3S)-3-[[5-fluoranyl-2-(5-fluoranyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid

Synonyms

3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid
VX787
(2S,3S)-3-((5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)bicyclo[2.2.2]octane-2-carboxylic acid

Systematic names

ProgramVersionName
ACDLabs 12.01 (1R,2S,3S,4R)-3-{[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino}bicyclo[2.2.2]octane-2-carboxylic acid
OpenEye OEToolkits 1.9.2 (2S,3S)-3-[[5-fluoranyl-2-(5-fluoranyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]bicyclo[2.2.2]octane-2-carboxylic acid

Formula

C20 H19 F2 N5 O2

Formal charge

0

Molecular weight

399.394 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=C(O)C5C1CCC(CC1)C5Nc2nc(ncc2F)c4c3cc(F)cnc3nc4
SMILES CACTVS 3.385 OC(=O)[CH]1C2CCC(CC2)[CH]1Nc3nc(ncc3F)c4c[nH]c5ncc(F)cc45
SMILES OpenEye OEToolkits 1.9.2 c1c(cnc2c1c(c[nH]2)c3ncc(c(n3)NC4C5CCC(C4C(=O)O)CC5)F)F
Canonical SMILES CACTVS 3.385 OC(=O)[C@H]1C2CCC(CC2)[C@@H]1Nc3nc(ncc3F)c4c[nH]c5ncc(F)cc45
Canonical SMILES OpenEye OEToolkits 1.9.2 c1c(cnc2c1c(c[nH]2)c3ncc(c(n3)N[C@@H]4[C@H](C5CCC4CC5)C(=O)O)F)F

IUPAC InChI

InChI=1S/C20H19F2N5O2/c21-11-5-12-13(7-24-17(12)23-6-11)18-25-8-14(22)19(27-18)26-16-10-3-1-9(2-4-10)15(16)20(28)29/h5-10,15-16H,1-4H2,(H,23,24)(H,28,29)(H,25,26,27)/t9-,10+,15-,16-/m0/s1

IUPAC InChI key

JGPXDNKSIXAZEQ-UIHHKEIPSA-N
21G

wwPDB Information

Atom count

48 (29 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2014-03-03

Last modified at

2020-11-26

Status

Released

Obsoleted

Not Assigned



21G : Atoms of Molecule

Total Number of Atoms: 48
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 4.499 -0.598 0.106
2 C2 C C2 N Y N 0 5.829 -0.214 0.142
3 C3 C C3 N Y N 0 6.156 1.122 -0.043
4 C5 C C4 N Y N 0 3.942 1.722 -0.3
5 C6 C C5 N Y N 0 3.538 0.388 -0.121
6 C7 C C6 N Y N 0 2.071 0.385 -0.234
7 N4 N N1 N Y N 0 5.23 2.034 -0.25
8 C8 C C7 N Y N 0 1.7 1.67 -0.464
9 N9 N N2 N Y N 0 2.803 2.468 -0.505
10 C11 C C8 N Y N 0 1.177 -0.787 -0.119
11 N12 N N3 N Y N 0 1.704 -1.982 0.115
12 C13 C C9 N Y N 0 0.935 -3.056 0.225
13 C14 C C10 N Y N 0 -0.435 -2.923 0.094
14 C15 C C11 N Y N 0 -0.962 -1.65 -0.153
15 N16 N N4 N Y N 0 -0.134 -0.617 -0.246
16 N17 N N5 N N N 0 -2.33 -1.47 -0.292
17 C18 C C12 S N N 0 -2.87 -0.133 -0.549
18 C20 C C13 S N N 0 -3.056 0.606 0.777
19 C22 C C14 N N N 0 -4.53 0.976 0.953
20 C23 C C15 N N N 0 -4.971 1.879 -0.201
21 C24 C C16 N N N 0 -4.785 1.14 -1.527
22 C25 C C17 N N N 0 -4.221 -0.256 -1.258
23 C26 C C18 N N N 0 -5.193 -1.037 -0.371
24 C27 C C19 N N N 0 -5.379 -0.298 0.955
25 C28 C C20 N N N 0 -2.221 1.861 0.775
26 O29 O O1 N N N 0 -0.889 1.779 0.633
27 O30 O O2 N N N 0 -2.75 2.939 0.9
28 F31 F F1 N N N 0 -1.247 -3.998 0.2
29 F32 F F2 N N N 0 6.798 -1.131 0.354
30 H1 H H1 N N N 0 4.214 -1.63 0.246
31 H2 H H2 N N N 0 7.194 1.42 -0.015
32 H3 H H3 N N N 0 0.683 2.009 -0.596
33 H4 H H4 N N N 0 2.789 3.427 -0.656
34 H5 H H5 N N N 0 1.374 -4.024 0.415
35 H6 H H6 N N N 0 -2.929 -2.229 -0.219
36 H7 H H7 N N N 0 -2.178 0.423 -1.181
37 H8 H H8 N N N 0 -2.743 -0.038 1.599
38 H9 H H9 N N N 0 -4.663 1.502 1.898
39 H10 H H10 N N N 0 -6.021 2.143 -0.075
40 H11 H H11 N N N 0 -4.367 2.787 -0.202
41 H12 H H12 N N N 0 -5.747 1.052 -2.032
42 H13 H H13 N N N 0 -4.092 1.696 -2.159
43 H14 H H14 N N N 0 -4.088 -0.783 -2.203
44 H15 H H15 N N N 0 -6.155 -1.125 -0.876
45 H16 H H16 N N N 0 -4.791 -2.032 -0.18
46 H17 H H17 N N N 0 -5.065 -0.942 1.777
47 H18 H H18 N N N 0 -6.429 -0.035 1.081
48 H19 H H19 N N N 0 -0.395 2.611 0.637



21G : Chemical Bonds

Total Number of Bonds: 52
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 N9 C5 N C sing 1.38 N Y
2 N9 C8 N C sing 1.36 N Y
3 N4 C5 N C sing 1.33 N Y
4 N4 C3 N C doub 1.32 N Y
5 C5 C6 C C doub 1.41 N Y
6 C8 C7 C C doub 1.36 N Y
7 C3 C2 C C sing 1.39 N Y
8 C6 C7 C C sing 1.47 N Y
9 C6 C1 C C sing 1.4 N Y
10 C7 C11 C C sing 1.48 N N
11 C2 C1 C C doub 1.38 N Y
12 C2 F32 C F sing 1.35 N N
13 N12 C11 N C doub 1.33 N Y
14 N12 C13 N C sing 1.33 N Y
15 C11 N16 C N sing 1.33 N Y
16 C13 C14 C C doub 1.38 N Y
17 N16 C15 N C doub 1.33 N Y
18 C15 C14 C C sing 1.4 N Y
19 C15 N17 C N sing 1.39 N N
20 C14 F31 C F sing 1.35 N N
21 O30 C28 O C doub 1.21 N N
22 N17 C18 N C sing 1.46 N N
23 C18 C25 C C sing 1.53 N N
24 C18 C20 C C sing 1.53 N N
25 C28 O29 C O sing 1.34 N N
26 C28 C20 C C sing 1.51 N N
27 C24 C25 C C sing 1.53 N N
28 C24 C23 C C sing 1.53 N N
29 C25 C26 C C sing 1.53 N N
30 C20 C22 C C sing 1.53 N N
31 C23 C22 C C sing 1.53 N N
32 C26 C27 C C sing 1.53 N N
33 C22 C27 C C sing 1.53 N N
34 C1 H1 C H sing 1.08 N N
35 C3 H2 C H sing 1.08 N N
36 C8 H3 C H sing 1.08 N N
37 N9 H4 N H sing 0.97 N N
38 C13 H5 C H sing 1.08 N N
39 N17 H6 N H sing 0.97 N N
40 C18 H7 C H sing 1.09 N N
41 C20 H8 C H sing 1.09 N N
42 C22 H9 C H sing 1.09 N N
43 C23 H10 C H sing 1.09 N N
44 C23 H11 C H sing 1.09 N N
45 C24 H12 C H sing 1.09 N N
46 C24 H13 C H sing 1.09 N N
47 C25 H14 C H sing 1.09 N N
48 C26 H15 C H sing 1.09 N N
49 C26 H16 C H sing 1.09 N N
50 C27 H17 C H sing 1.09 N N
51 C27 H18 C H sing 1.09 N N
52 O29 H19 O H sing 0.97 N N



21G : Used in PDB Entries

Total Number of PDB Entries: 7
Ligand Code PDB Entry ID Type Total Distinct
21G 4p1u Open in New Window Bound ligand 1 1
21G 5wl0 Open in New Window Bound ligand 1 1
21G 6euv Open in New Window Bound ligand 6 1
21G 7as0 Open in New Window Bound ligand 1 1
21G 7as1 Open in New Window Bound ligand 1 1
21G 7as2 Open in New Window Bound ligand 1 1
21G 7as3 Open in New Window Bound ligand 2 1