Chemical Components in the PDB

pdbe.org/chem
wwPDB
EMDataBank
spacer

WAM : Summary

Code

WAM

One-letter code

X

Molecule name

2-[(~{E})-2-(3-methoxy-4-oxidanyl-phenyl)ethenyl]-1-methyl-quinoline-4-carboxamide

Systematic names

ProgramVersionName
ACDLabs 12.01 4-carbamoyl-2-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-1-methylquinolin-1-ium
OpenEye OEToolkits 2.0.7 2-[(~{E})-2-(3-methoxy-4-oxidanyl-phenyl)ethenyl]-1-methyl-quinolin-1-ium-4-carboxamide

Formula

C20 H19 N2 O3

Formal charge

1

Molecular weight

335.376 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 C[n+]1c(cc(c2c1cccc2)C(=O)N)[C@H]=[C@H]c3cc(OC)c(cc3)O
SMILES CACTVS 3.385 COc1cc(ccc1O)C=Cc2cc(C(N)=O)c3ccccc3[n+]2C
SMILES OpenEye OEToolkits 2.0.7 C[n+]1c2ccccc2c(cc1C=Cc3ccc(c(c3)OC)O)C(=O)N
Canonical SMILES CACTVS 3.385 COc1cc(ccc1O)\C=C\c2cc(C(N)=O)c3ccccc3[n+]2C
Canonical SMILES OpenEye OEToolkits 2.0.7 C[n+]1c2ccccc2c(cc1/C=C/c3ccc(c(c3)OC)O)C(=O)N

IUPAC InChI

InChI=1S/C20H18N2O3/c1-22-14(9-7-13-8-10-18(23)19(11-13)25-2)12-16(20(21)24)15-5-3-4-6-17(15)22/h3-12H,1-2H3,(H2,21,24)/p+1

IUPAC InChI key

VIXQOJJAMXIXBH-UHFFFAOYSA-O
WAM

wwPDB Information

Atom count

44 (25 without Hydrogen)

Polymer type

Bound ligand

Type description

non-polymer

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2020-10-05

Last modified at

2021-06-18

Status

Released

Obsoleted

Not Assigned



WAM : Atoms of Molecule

Total Number of Atoms: 44
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 1.507 2.876 -0.055
2 C2 C C2 N Y N 0 1.074 0.517 -0.089
3 C3 C C3 N Y N 0 1.439 -0.842 -0.084
4 N1 N N1 N Y N 1 1.969 1.486 -0.045
5 C8 C C7 N Y N 0 4.211 2.297 0.054
6 C8A C C4 N Y N 0 3.28 1.243 0.007
7 C4A C C5 N Y N 0 3.754 -0.093 0.018
8 C4 C C6 N Y N 0 2.781 -1.186 -0.031
9 C5 C C8 N Y N 0 5.129 -0.342 0.074
10 C9 C C9 N N N 0 -0.353 0.869 -0.152
11 C7 C C10 N Y N 0 5.543 2.019 0.108
12 C6 C C11 N Y N 0 6.003 0.704 0.119
13 C19 C C12 N N N 0 3.213 -2.6 -0.022
14 O19 O O1 N N N 0 4.386 -2.877 0.129
15 N19 N N2 N N N 0 2.304 -3.583 -0.183
16 C16 C C16 N Y N 0 -3.1 1.605 -0.049
17 C10 C C13 N N N 0 -1.287 -0.097 -0.102
18 C11 C C14 N Y N 0 -2.714 0.261 -0.051
19 C12 C C15 N Y N 0 -3.687 -0.742 0.002
20 C13 C C17 N Y N 0 -5.025 -0.4 0.049
21 C15 C C18 N Y N 0 -4.437 1.938 -0.001
22 C14 C C19 N Y N 0 -5.402 0.942 0.045
23 O14 O O2 N N N 0 -6.719 1.275 0.091
24 O13 O O3 N N N 0 -5.974 -1.373 0.101
25 CM13 C C20 N N N 0 -5.516 -2.727 0.102
26 HM12 H H1 N N N 0 1.267 3.186 0.962
27 HM11 H H2 N N N 0 2.293 3.517 -0.454
28 HM13 H H3 N N N 0 0.618 2.959 -0.68
29 H3 H H4 N N N 0 0.681 -1.611 -0.12
30 H8 H H5 N N N 0 3.871 3.322 0.047
31 H5 H H6 N N N 0 5.497 -1.358 0.082
32 H9 H H7 N N N 0 -0.65 1.904 -0.239
33 H7 H H8 N N N 0 6.254 2.831 0.143
34 H6 H H9 N N N 0 7.064 0.511 0.162
35 H192 H H10 N N N 0 1.367 -3.362 -0.304
36 H191 H H11 N N N 0 2.587 -4.511 -0.177
37 H10 H H12 N N N 0 -0.99 -1.135 -0.099
38 H12 H H13 N N N 0 -3.394 -1.781 0.005
39 H15 H H15 N N N 0 -4.734 2.976 0.001
40 H16 H H14 N N N 0 -2.351 2.382 -0.084
41 H14 H H16 N N N 0 -7.133 1.364 -0.778
42 H132 H H17 N N N 0 -4.878 -2.893 0.97
43 H133 H H18 N N N 0 -6.372 -3.4 0.145
44 H131 H H19 N N N 0 -4.948 -2.919 -0.808



WAM : Chemical Bonds

Total Number of Bonds: 46
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C15 C16 C C doub 1.38 N Y
2 C15 C14 C C sing 1.39 N Y
3 C16 C11 C C sing 1.4 N Y
4 O14 C14 O C sing 1.36 N N
5 C14 C13 C C doub 1.39 N Y
6 N19 C19 N C sing 1.35 N N
7 C11 C10 C C sing 1.47 N N
8 C11 C12 C C doub 1.4 N Y
9 C10 C9 C C doub 1.34 E N
10 C13 C12 C C sing 1.38 N Y
11 C13 O13 C O sing 1.36 N N
12 C19 C4 C C sing 1.48 N N
13 C19 O19 C O doub 1.21 N N
14 O13 CM13 O C sing 1.43 N N
15 C3 C4 C C doub 1.39 N Y
16 C3 C2 C C sing 1.41 N Y
17 C4 C4A C C sing 1.46 N Y
18 C9 C2 C C sing 1.47 N N
19 C5 C4A C C doub 1.4 N Y
20 C5 C6 C C sing 1.36 N Y
21 C2 N1 C N doub 1.32 N Y
22 C4A C8A C C sing 1.42 N Y
23 C6 C7 C C doub 1.39 N Y
24 C7 C8 C C sing 1.36 N Y
25 C8A C8 C C doub 1.41 N Y
26 C8A N1 C N sing 1.33 N Y
27 N1 C1 N C sing 1.46 N N
28 C1 HM12 C H sing 1.09 N N
29 C1 HM11 C H sing 1.09 N N
30 C1 HM13 C H sing 1.09 N N
31 C3 H3 C H sing 1.08 N N
32 C8 H8 C H sing 1.08 N N
33 C5 H5 C H sing 1.08 N N
34 C9 H9 C H sing 1.08 N N
35 C7 H7 C H sing 1.08 N N
36 C6 H6 C H sing 1.08 N N
37 N19 H192 N H sing 0.97 N N
38 N19 H191 N H sing 0.97 N N
39 C10 H10 C H sing 1.08 N N
40 C12 H12 C H sing 1.08 N N
41 C16 H16 C H sing 1.08 N N
42 C15 H15 C H sing 1.08 N N
43 O14 H14 O H sing 0.97 N N
44 CM13 H132 C H sing 1.09 N N
45 CM13 H133 C H sing 1.09 N N
46 CM13 H131 C H sing 1.09 N N



WAM : Used in PDB Entries

Total Number of PDB Entries: 2
Ligand Code PDB Entry ID Type Total Distinct
WAM 7kbw Open in New Window Bound ligand 2 1
WAM 7kbx Open in New Window Bound ligand 2 1