Chemical Components in the PDB

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ASW : Summary

Code

ASW

One-letter code

X

Molecule name

N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide

Synonyms

Amsacrine

Systematic names

ProgramVersionName
ACDLabs 12.01 N-[4-(acridin-9-ylamino)-3-methoxyphenyl]methanesulfonamide
OpenEye OEToolkits 1.7.6 N-[4-(acridin-9-ylamino)-3-methoxy-phenyl]methanesulfonamide

Formula

C21 H19 N3 O3 S

Formal charge

0

Molecular weight

393.459 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=S(=O)(Nc1ccc(c(OC)c1)Nc2c4c(nc3c2cccc3)cccc4)C
SMILES CACTVS 3.370 COc1cc(N[S](C)(=O)=O)ccc1Nc2c3ccccc3nc4ccccc24
SMILES OpenEye OEToolkits 1.7.6 COc1cc(ccc1Nc2c3ccccc3nc4c2cccc4)NS(=O)(=O)C
Canonical SMILES CACTVS 3.370 COc1cc(N[S](C)(=O)=O)ccc1Nc2c3ccccc3nc4ccccc24
Canonical SMILES OpenEye OEToolkits 1.7.6 COc1cc(ccc1Nc2c3ccccc3nc4c2cccc4)NS(=O)(=O)C

IUPAC InChI

InChI=1S/C21H19N3O3S/c1-27-20-13-14(24-28(2,25)26)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13,24H,1-2H3,(H,22,23)

IUPAC InChI key

XCPGHVQEEXUHNC-UHFFFAOYSA-N
ASW

wwPDB Information

Atom count

47 (28 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2012-07-25

Last modified at

2013-07-12

Status

Released

Obsoleted

Not Assigned



ASW : Atoms of Molecule

Total Number of Atoms: 47
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C1 C C1 N N N 0 1.829 3.333 2.969
2 O2 O O2 N N N 0 0.78 2.554 2.39
3 C3 C C3 N Y N 0 1.136 1.65 1.439
4 C4 C C4 N Y N 0 2.464 1.513 1.075
5 C5 C C5 N Y N 0 2.825 0.589 0.104
6 N6 N N6 N N N 0 4.168 0.449 -0.264
7 S7 S S7 N N N 0 4.654 -0.871 -1.138
8 C8 C C8 N N N 0 4.276 -2.287 -0.068
9 O9 O O9 N N N 0 3.806 -0.868 -2.278
10 O10 O O10 N N N 0 6.059 -0.706 -1.269
11 C11 C C11 N Y N 0 1.854 -0.197 -0.503
12 C12 C C12 N Y N 0 0.527 -0.061 -0.142
13 C13 C C13 N Y N 0 0.163 0.857 0.832
14 N14 N N14 N N N 0 -1.182 0.991 1.202
15 C15 C C15 N Y N 0 -2.156 0.298 0.517
16 C16 C C16 N Y N 0 -2.894 0.908 -0.517
17 C17 C C17 N Y N 0 -2.656 2.244 -0.882
18 C18 C C18 N Y N 0 -3.383 2.809 -1.884
19 C19 C C19 N Y N 0 -4.363 2.078 -2.556
20 C20 C C20 N Y N 0 -4.62 0.784 -2.231
21 C21 C C21 N Y N 0 -3.89 0.161 -1.199
22 N22 N N22 N Y N 0 -4.133 -1.107 -0.87
23 C23 C C23 N Y N 0 -3.462 -1.724 0.101
24 C24 C C24 N Y N 0 -3.746 -3.067 0.422
25 C25 C C25 N Y N 0 -3.053 -3.686 1.416
26 C26 C C26 N Y N 0 -2.06 -3.014 2.128
27 C27 C C27 N Y N 0 -1.756 -1.718 1.848
28 C28 C C28 N Y N 0 -2.446 -1.047 0.825
29 H1 H H1 N N N 0 1.41 4.013 3.711
30 H2 H H2 N N N 0 2.55 2.672 3.449
31 H3 H H3 N N N 0 2.327 3.909 2.189
32 H4 H H4 N N N 0 3.22 2.124 1.547
33 H5 H H5 N N N 0 4.814 1.125 -0.0070
34 H6 H H6 N N N 0 3.196 -2.378 0.047
35 H7 H H7 N N N 0 4.672 -3.198 -0.517
36 H8 H H8 N N N 0 4.734 -2.136 0.91
37 H9 H H9 N N N 0 2.137 -0.915 -1.259
38 H10 H H10 N N N 0 -0.226 -0.672 -0.616
39 H11 H H11 N N N 0 -1.427 1.571 1.939
40 H12 H H12 N N N 0 -1.901 2.821 -0.368
41 H13 H H13 N N N 0 -3.199 3.836 -2.163
42 H14 H H14 N N N 0 -4.926 2.549 -3.348
43 H15 H H15 N N N 0 -5.383 0.234 -2.762
44 H16 H H16 N N N 0 -4.512 -3.603 -0.118
45 H17 H H17 N N N 0 -3.276 -4.715 1.657
46 H18 H H18 N N N 0 -1.529 -3.529 2.916
47 H19 H H19 N N N 0 -0.985 -1.209 2.408



ASW : Chemical Bonds

Total Number of Bonds: 50
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C1 O2 C O sing 1.43 N N
2 O2 C3 O C sing 1.36 N N
3 O10 S7 O S doub 1.42 N N
4 C4 C3 C C doub 1.38 N Y
5 C4 C5 C C sing 1.39 N Y
6 C8 S7 C S sing 1.81 N N
7 C3 C13 C C sing 1.39 N Y
8 S7 N6 S N sing 1.66 N N
9 S7 O9 S O doub 1.42 N N
10 N6 C5 N C sing 1.4 N N
11 C5 C11 C C doub 1.39 N Y
12 C26 C27 C C doub 1.36 N Y
13 C26 C25 C C sing 1.39 N Y
14 C27 C28 C C sing 1.4 N Y
15 C13 N14 C N sing 1.4 N N
16 C13 C12 C C doub 1.39 N Y
17 N14 C15 N C sing 1.38 N N
18 C25 C24 C C doub 1.36 N Y
19 C11 C12 C C sing 1.38 N Y
20 C28 C15 C C doub 1.41 N Y
21 C28 C23 C C sing 1.42 N Y
22 C15 C16 C C sing 1.41 N Y
23 C24 C23 C C sing 1.41 N Y
24 C23 N22 C N doub 1.33 N Y
25 C16 C17 C C doub 1.41 N Y
26 C16 C21 C C sing 1.42 N Y
27 C17 C18 C C sing 1.36 N Y
28 N22 C21 N C sing 1.33 N Y
29 C21 C20 C C doub 1.41 N Y
30 C18 C19 C C doub 1.4 N Y
31 C20 C19 C C sing 1.36 N Y
32 C1 H1 C H sing 1.09 N N
33 C1 H2 C H sing 1.09 N N
34 C1 H3 C H sing 1.09 N N
35 C4 H4 C H sing 1.08 N N
36 N6 H5 N H sing 0.97 N N
37 C8 H6 C H sing 1.09 N N
38 C8 H7 C H sing 1.09 N N
39 C8 H8 C H sing 1.09 N N
40 C11 H9 C H sing 1.08 N N
41 C12 H10 C H sing 1.08 N N
42 N14 H11 N H sing 0.97 N N
43 C17 H12 C H sing 1.08 N N
44 C18 H13 C H sing 1.08 N N
45 C19 H14 C H sing 1.08 N N
46 C20 H15 C H sing 1.08 N N
47 C24 H16 C H sing 1.08 N N
48 C25 H17 C H sing 1.08 N N
49 C26 H18 C H sing 1.08 N N
50 C27 H19 C H sing 1.08 N N



ASW : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
ASW 4g0u Open in New Window Bound ligand 2 1