Chemical Components in the PDB

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0WN : Summary

Code

0WN

One-letter code

X

Molecule name

N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)butanamide

Synonyms

Afatinib, bound form

Systematic names

ProgramVersionName
ACDLabs 12.01 N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)butanamide
OpenEye OEToolkits 1.7.6 N-[4-[(3-chloranyl-4-fluoranyl-phenyl)amino]-7-[(3S)-oxolan-3-yl]oxy-quinazolin-6-yl]-4-(dimethylamino)butanamide

Formula

C24 H27 Cl F N5 O3

Formal charge

0

Molecular weight

487.954 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 Fc1ccc(cc1Cl)Nc4ncnc3cc(OC2CCOC2)c(cc34)NC(=O)CCCN(C)C
SMILES CACTVS 3.370 CN(C)CCCC(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[CH]4CCOC4
SMILES OpenEye OEToolkits 1.7.6 CN(C)CCCC(=O)Nc1cc2c(cc1OC3CCOC3)ncnc2Nc4ccc(c(c4)Cl)F
Canonical SMILES CACTVS 3.370 CN(C)CCCC(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[C@H]4CCOC4
Canonical SMILES OpenEye OEToolkits 1.7.6 CN(C)CCCC(=O)Nc1cc2c(cc1O[C@H]3CCOC3)ncnc2Nc4ccc(c(c4)Cl)F

IUPAC InChI

InChI=1S/C24H27ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h5-6,10-12,14,16H,3-4,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/t16-/m0/s1

IUPAC InChI key

JSENTLOBWVHLNR-INIZCTEOSA-N
0WN

wwPDB Information

Atom count

61 (34 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2012-07-27

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



0WN : Atoms of Molecule

Total Number of Atoms: 61
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 2.395 2.933 -0.958
2 N2 N N2 N Y N 0 2.754 1.685 -0.704
3 N3 N N3 N Y N 0 1.154 3.351 -0.869
4 C4 C C4 N Y N 0 1.866 0.769 -0.339
5 C5 C C5 N Y N 0 0.175 2.505 -0.513
6 C6 C C6 N Y N 0 0.51 1.159 -0.225
7 C7 C C7 N Y N 0 -1.794 0.687 0.251
8 C8 C C8 N Y N 0 -0.489 0.256 0.155
9 C9 C C9 N Y N 0 -2.128 2.018 -0.04
10 C10 C C10 N Y N 0 -1.158 2.922 -0.409
11 N11 N N11 N N N 0 2.255 -0.529 -0.077
12 C12 C C12 N Y N 0 5.899 -0.279 0.348
13 C13 C C13 N Y N 0 6.299 -1.536 -0.079
14 C14 C C14 N Y N 0 4.558 0.056 0.35
15 C15 C C15 N Y N 0 5.357 -2.457 -0.504
16 C16 C C16 N Y N 0 3.612 -0.867 -0.077
17 C17 C C17 N Y N 0 4.016 -2.125 -0.505
18 F18 F F18 N N N 0 7.61 -1.863 -0.079
19 CL1 CL CL1 N N N 0 7.082 0.871 0.889
20 O20 O O20 N N N 0 -3.424 2.42 0.044
21 C21 C C21 S N N 0 -3.715 3.759 -0.359
22 C22 C C22 N N N 0 -3.596 4.724 0.842
23 O23 O O23 N N N 0 -4.66 5.682 0.652
24 C24 C C24 N N N 0 -5.79 4.909 0.192
25 C25 C C25 N N N 0 -5.192 3.884 -0.796
26 N26 N N26 N N N 0 -2.798 -0.216 0.625
27 C27 C C27 N N N 0 -2.68 -1.522 0.315
28 C28 C C28 N N N 0 -3.803 -2.476 0.63
29 O29 O O29 N N N 0 -1.669 -1.929 -0.217
30 C30 C C30 N N N 0 -3.416 -3.886 0.179
31 C31 C C31 N N N 0 -4.556 -4.854 0.499
32 N32 N N32 N N N 0 -4.185 -6.208 0.066
33 C33 C C33 N N N 0 -5.144 -7.202 0.565
34 C34 C C34 N N N 0 -4.065 -6.279 -1.396
35 H1 H H1 N N N 0 3.158 3.641 -1.248
36 H2 H H2 N N N 0 -0.239 -0.772 0.371
37 H6 H H6 N N N 0 5.671 -3.435 -0.837
38 H3 H H3 N N N 0 -1.423 3.948 -0.618
39 H4 H H4 N N N 0 1.586 -1.208 0.107
40 H5 H H5 N N N 0 4.247 1.035 0.683
41 H7 H H7 N N N 0 3.282 -2.843 -0.837
42 H8 H H8 N N N 0 -3.05 4.067 -1.167
43 H9 H H9 N N N 0 -3.734 4.183 1.778
44 H10 H H10 N N N 0 -2.628 5.225 0.831
45 H11 H H11 N N N 0 -6.265 4.397 1.029
46 H12 H H12 N N N 0 -6.509 5.553 -0.315
47 H13 H H13 N N N 0 -5.257 4.256 -1.819
48 H14 H H14 N N N 0 -5.7 2.924 -0.705
49 H15 H H15 N N N 0 -3.578 0.1 1.108
50 H16 H H16 N N N 0 -3.989 -2.476 1.704
51 H17 H H17 N N N 0 -4.705 -2.161 0.105
52 H18 H H18 N N N 0 -3.23 -3.886 -0.895
53 H19 H H19 N N Y 0 -2.514 -4.2 0.704
54 H24 H H24 N N N 0 -5.162 -7.176 1.654
55 H20 H H20 N N N 0 -4.743 -4.855 1.573
56 H21 H H21 N N N 0 -5.458 -4.54 -0.026
57 H23 H H23 N N N 0 -4.846 -8.196 0.23
58 H25 H H25 N N N 0 -6.138 -6.973 0.18
59 H26 H H26 N N N 0 -3.298 -5.582 -1.733
60 H27 H H27 N N N 0 -3.79 -7.292 -1.69
61 H28 H H28 N N N 0 -5.02 -6.016 -1.852



0WN : Chemical Bonds

Total Number of Bonds: 64
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 F18 C13 F C sing 1.35 N N
2 C13 C15 C C doub 1.38 N Y
3 C13 C12 C C sing 1.39 N Y
4 CL1 C12 CL C sing 1.74 N N
5 C15 C17 C C sing 1.38 N Y
6 C12 C14 C C doub 1.38 N Y
7 C17 C16 C C doub 1.39 N Y
8 C14 C16 C C sing 1.39 N Y
9 C16 N11 C N sing 1.4 N N
10 N11 C4 N C sing 1.38 N N
11 N2 C4 N C doub 1.33 N Y
12 N2 C1 N C sing 1.32 N Y
13 C4 C6 C C sing 1.42 N Y
14 C1 N3 C N doub 1.31 N Y
15 C6 C8 C C doub 1.4 N Y
16 C6 C5 C C sing 1.42 N Y
17 C33 N32 C N sing 1.47 N N
18 C8 C7 C C sing 1.38 N Y
19 N3 C5 N C sing 1.34 N Y
20 C5 C10 C C doub 1.4 N Y
21 O29 C27 O C doub 1.21 N N
22 N32 C34 N C sing 1.47 N N
23 N32 C31 N C sing 1.47 N N
24 C7 N26 C N sing 1.4 N N
25 C7 C9 C C doub 1.4 N Y
26 C10 C9 C C sing 1.38 N Y
27 C27 N26 C N sing 1.35 N N
28 C27 C28 C C sing 1.51 N N
29 C9 O20 C O sing 1.36 N N
30 C31 C30 C C sing 1.53 N N
31 C30 C28 C C sing 1.53 N N
32 O20 C21 O C sing 1.43 N N
33 C22 C21 C C sing 1.55 N N
34 C22 O23 C O sing 1.44 N N
35 C21 C25 C C sing 1.55 N N
36 O23 C24 O C sing 1.44 N N
37 C25 C24 C C sing 1.54 N N
38 C1 H1 C H sing 1.08 N N
39 C8 H2 C H sing 1.08 N N
40 C10 H3 C H sing 1.08 N N
41 N11 H4 N H sing 0.97 N N
42 C14 H5 C H sing 1.08 N N
43 C15 H6 C H sing 1.08 N N
44 C17 H7 C H sing 1.08 N N
45 C21 H8 C H sing 1.09 N N
46 C22 H9 C H sing 1.09 N N
47 C22 H10 C H sing 1.09 N N
48 C24 H11 C H sing 1.09 N N
49 C24 H12 C H sing 1.09 N N
50 C25 H13 C H sing 1.09 N N
51 C25 H14 C H sing 1.09 N N
52 N26 H15 N H sing 0.97 N N
53 C28 H16 C H sing 1.09 N N
54 C28 H17 C H sing 1.09 N N
55 C30 H18 C H sing 1.09 N N
56 C30 H19 C H sing 1.09 N N
57 C31 H20 C H sing 1.09 N N
58 C31 H21 C H sing 1.09 N N
59 C33 H23 C H sing 1.09 N N
60 C33 H24 C H sing 1.09 N N
61 C33 H25 C H sing 1.09 N N
62 C34 H26 C H sing 1.09 N N
63 C34 H27 C H sing 1.09 N N
64 C34 H28 C H sing 1.09 N N



0WN : Used in PDB Entries

Total Number of PDB Entries: 3
Ligand Code PDB Entry ID Type Total Distinct
0WN 4g5j Open in New Window Bound ligand 1 1
0WN 4g5p Open in New Window Bound ligand 1 1
0WN 6zu8 Open in New Window Bound ligand 1 1