Chemical Components in the PDB

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3W5 : Summary

Code

3W5

One-letter code

X

Molecule name

N-[(3S)-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]-4-(4-{[(3S)-3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl]ethynyl}phenoxy)benzamide

Systematic names

ProgramVersionName
ACDLabs 12.01 N-[(3S)-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]-4-(4-{[(3S)-3-hydroxy-1-azabicyclo[2.2.2]oct-3-yl]ethynyl}phenoxy)benzamide
OpenEye OEToolkits 1.9.2 N-[(3S)-1,1-bis(oxidanylidene)thian-3-yl]-4-[4-[2-[(3S)-3-oxidanyl-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]phenoxy]benzamide

Formula

C27 H30 N2 O5 S

Formal charge

0

Molecular weight

494.603 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=S5(=O)CCCC(NC(=O)c4ccc(Oc3ccc(C#CC2(O)C1CCN(CC1)C2)cc3)cc4)C5
SMILES CACTVS 3.385 O[C]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)N[CH]5CCC[S](=O)(=O)C5)cc3
SMILES OpenEye OEToolkits 1.9.2 c1cc(ccc1C#CC2(CN3CCC2CC3)O)Oc4ccc(cc4)C(=O)NC5CCCS(=O)(=O)C5
Canonical SMILES CACTVS 3.385 O[C@]1(CN2CCC1CC2)C#Cc3ccc(Oc4ccc(cc4)C(=O)N[C@H]5CCC[S](=O)(=O)C5)cc3
Canonical SMILES OpenEye OEToolkits 1.9.2 c1cc(ccc1C#C[C@@]2(CN3CCC2CC3)O)Oc4ccc(cc4)C(=O)N[C@H]5CCCS(=O)(=O)C5

IUPAC InChI

InChI=1S/C27H30N2O5S/c30-26(28-23-2-1-17-35(32,33)18-23)21-5-9-25(10-6-21)34-24-7-3-20(4-8-24)11-14-27(31)19-29-15-12-22(27)13-16-29/h3-10,22-23,31H,1-2,12-13,15-19H2,(H,28,30)/t23-,27-/m0/s1

IUPAC InChI key

IOEYWFCDGXVEFG-HOFKKMOUSA-N
3W5

wwPDB Information

Atom count

65 (35 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2011-11-11

Last modified at

2014-09-05

Status

Released

Obsoleted

Not Assigned



3W5 : Atoms of Molecule

Total Number of Atoms: 65
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 3.016 1.047 -1.111
2 C2 C C2 N Y N 0 1.93 1.895 -1.085
3 C3 C C3 N Y N 0 1.609 2.579 0.08
4 C4 C C4 N Y N 0 2.379 2.411 1.223
5 C5 C C5 N Y N 0 3.467 1.565 1.205
6 C6 C C6 N Y N 0 3.793 0.875 0.036
7 C7 C C7 N N N 0 4.922 -0.005 0.013
8 C8 C C8 N N N 0 5.847 -0.728 -0.005
9 C9 C C9 S N N 0 7.008 -1.633 -0.028
10 C10 C C10 N N N 0 7.681 -1.639 1.347
11 N1 N N1 N N N 0 9.07 -1.178 1.212
12 C11 C C11 N N N 0 9.844 -2.079 0.347
13 C12 C C12 N N N 0 9.231 -2.086 -1.057
14 C13 C C13 N N N 0 8.019 -1.146 -1.073
15 C14 C C14 N N N 0 8.487 0.262 -0.682
16 C15 C C15 N N N 0 9.121 0.203 0.711
17 O1 O O1 N N N 0 6.577 -2.956 -0.356
18 O2 O O2 N N N 0 0.538 3.415 0.101
19 C16 C C16 N Y N 0 -0.699 2.869 -0.017
20 C21 C C21 N Y N 0 -1.812 3.693 -0.134
21 C20 C C20 N Y N 0 -3.069 3.143 -0.253
22 C19 C C19 N Y N 0 -3.224 1.754 -0.257
23 C18 C C18 N Y N 0 -2.102 0.929 -0.14
24 C17 C C17 N Y N 0 -0.848 1.487 -0.026
25 C22 C C22 N N N 0 -4.569 1.161 -0.384
26 O3 O O3 N N N 0 -5.544 1.88 -0.486
27 N2 N N2 N N N 0 -4.717 -0.179 -0.388
28 C23 C C23 S N N 0 -6.052 -0.769 -0.514
29 C24 C C24 N N N 0 -5.933 -2.172 -1.102
30 C25 C C25 N N N 0 -7.308 -2.716 -1.479
31 C26 C C26 N N N 0 -8.117 -3.014 -0.215
32 S1 S S1 N N N 0 -8.406 -1.461 0.682
33 O5 O O5 N N N 0 -9.131 -0.577 -0.161
34 O4 O O4 N N N 0 -8.919 -1.769 1.971
35 C27 C C27 N N N 0 -6.711 -0.834 0.866
36 H1 H H1 N N N 0 3.263 0.512 -2.016
37 H2 H H2 N N N 0 1.329 2.029 -1.973
38 H4 H H4 N N N 0 2.126 2.945 2.127
39 H5 H H5 N N N 0 4.067 1.436 2.094
40 H101 H H101 N N N 0 7.141 -0.974 2.02
41 H102 H H102 N N N 0 7.673 -2.651 1.752
42 H13 H H13 N N N 0 7.563 -1.14 -2.063
43 HA H HA N N N 0 5.938 -3.327 0.268
44 H111 H H111 N N N 0 10.876 -1.733 0.292
45 H112 H H112 N N N 0 9.82 -3.088 0.759
46 H151 H H151 N N N 0 8.57 0.856 1.389
47 H152 H H152 N N N 0 10.159 0.53 0.653
48 H121 H H121 N N N 0 9.971 -1.742 -1.78
49 H122 H H122 N N N 0 8.912 -3.097 -1.311
50 H141 H H141 N N N 0 9.224 0.616 -1.403
51 H142 H H142 N N N 0 7.634 0.939 -0.666
52 H17 H H17 N N N 0 0.02 0.85 0.061
53 H21 H H21 N N N 0 -1.691 4.766 -0.131
54 H18 H H18 N N N 0 -2.218 -0.145 -0.142
55 H20 H H20 N N N 0 -3.933 3.784 -0.343
56 HB H HB N N N 0 -3.939 -0.753 -0.307
57 H23 H H23 N N N 0 -6.66 -0.15 -1.174
58 H241 H H241 N N N 0 -5.304 -2.136 -1.992
59 H242 H H242 N N N 0 -5.475 -2.832 -0.366
60 H271 H H271 N N N 0 -6.142 -1.504 1.51
61 H272 H H272 N N N 0 -6.736 0.163 1.306
62 H251 H H251 N N N 0 -7.836 -1.977 -2.081
63 H252 H H252 N N N 0 -7.188 -3.632 -2.057
64 H261 H H261 N N N 0 -9.073 -3.46 -0.49
65 H262 H H262 N N N 0 -7.56 -3.703 0.42



3W5 : Chemical Bonds

Total Number of Bonds: 69
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C1 C2 C C sing 1.38 N Y
2 C1 C6 C C doub 1.4 N Y
3 C2 C3 C C doub 1.39 N Y
4 C3 C4 C C sing 1.39 N Y
5 C3 O2 C O sing 1.36 N N
6 C4 C5 C C doub 1.38 N Y
7 C5 C6 C C sing 1.4 N Y
8 C6 C7 C C sing 1.43 N N
9 C7 C8 C C trip 1.17 N N
10 C8 C9 C C sing 1.47 N N
11 C9 C10 C C sing 1.53 N N
12 C9 C13 C C sing 1.53 N N
13 C9 O1 C O sing 1.43 N N
14 C10 N1 C N sing 1.47 N N
15 N1 C11 N C sing 1.47 N N
16 N1 C15 N C sing 1.47 N N
17 C11 C12 C C sing 1.53 N N
18 C12 C13 C C sing 1.53 N N
19 C13 C14 C C sing 1.53 N N
20 C14 C15 C C sing 1.53 N N
21 O2 C16 O C sing 1.36 N N
22 C16 C17 C C doub 1.39 N Y
23 C16 C21 C C sing 1.39 N Y
24 C17 C18 C C sing 1.38 N Y
25 C18 C19 C C doub 1.4 N Y
26 C19 C20 C C sing 1.4 N Y
27 C19 C22 C C sing 1.48 N N
28 C20 C21 C C doub 1.38 N Y
29 C22 O3 C O doub 1.22 N N
30 C22 N2 C N sing 1.35 N N
31 N2 C23 N C sing 1.46 N N
32 C23 C24 C C sing 1.53 N N
33 C23 C27 C C sing 1.53 N N
34 C24 C25 C C sing 1.53 N N
35 C25 C26 C C sing 1.53 N N
36 C26 S1 C S sing 1.82 N N
37 S1 O4 S O doub 1.42 N N
38 S1 O5 S O doub 1.42 N N
39 S1 C27 S C sing 1.82 N N
40 C1 H1 C H sing 1.08 N N
41 C2 H2 C H sing 1.08 N N
42 C4 H4 C H sing 1.08 N N
43 C5 H5 C H sing 1.08 N N
44 C10 H101 C H sing 1.09 N N
45 C10 H102 C H sing 1.09 N N
46 C13 H13 C H sing 1.09 N N
47 O1 HA O H sing 0.97 N N
48 C11 H111 C H sing 1.09 N N
49 C11 H112 C H sing 1.09 N N
50 C15 H151 C H sing 1.09 N N
51 C15 H152 C H sing 1.09 N N
52 C12 H121 C H sing 1.09 N N
53 C12 H122 C H sing 1.09 N N
54 C14 H141 C H sing 1.09 N N
55 C14 H142 C H sing 1.09 N N
56 C17 H17 C H sing 1.08 N N
57 C21 H21 C H sing 1.08 N N
58 C18 H18 C H sing 1.08 N N
59 C20 H20 C H sing 1.08 N N
60 N2 HB N H sing 0.97 N N
61 C23 H23 C H sing 1.09 N N
62 C24 H241 C H sing 1.09 N N
63 C24 H242 C H sing 1.09 N N
64 C27 H271 C H sing 1.09 N N
65 C27 H272 C H sing 1.09 N N
66 C25 H251 C H sing 1.09 N N
67 C25 H252 C H sing 1.09 N N
68 C26 H261 C H sing 1.09 N N
69 C26 H262 C H sing 1.09 N N



3W5 : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
3W5 4a7b Open in New Window Bound ligand 1 1