Chemical Components in the PDB

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QI9 : Summary

Code

QI9

One-letter code

X

Molecule name

Quinine

Synonyms

(3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol

Systematic names

ProgramVersionName
ACDLabs 12.01 (3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol
OpenEye OEToolkits 1.9.2 (R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol

Formula

C20 H24 N2 O2

Formal charge

0

Molecular weight

324.417 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O(c4cc1c(nccc1C(O)C2N3CCC(C2)C(/C=C)C3)cc4)C
SMILES CACTVS 3.385 COc1ccc2nccc([CH](O)[CH]3C[CH]4CC[N]3C[CH]4C=C)c2c1
SMILES OpenEye OEToolkits 1.9.2 COc1ccc2c(c1)c(ccn2)C(C3CC4CCN3CC4C=C)O
Canonical SMILES CACTVS 3.385 COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)c2c1
Canonical SMILES OpenEye OEToolkits 1.9.2 COc1ccc2c(c1)c(ccn2)[C@H]([C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)O

IUPAC InChI

InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1

IUPAC InChI key

LOUPRKONTZGTKE-WZBLMQSHSA-N
QI9

wwPDB Information

Atom count

48 (24 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2014-10-15

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



QI9 : 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 C C C20 N N N 0 -4.813 3.175 0.377
2 C1 C C19 N Y N 0 -3.344 1.31 0.247
3 C10 C C1 R N N 0 0.321 -0.683 1.199
4 C11 C C2 S N N 0 1.229 0.187 0.327
5 C12 C C10 N N N 0 2.038 -0.705 -0.618
6 C13 C C9 S N N 0 3.532 -0.494 -0.342
7 C14 C C4 N N N 0 3.812 -0.846 1.125
8 C15 C C3 N N N 0 2.954 0.051 2.022
9 C16 C C5 N N N 0 3.006 1.833 0.383
10 C17 C C6 R N N 0 3.865 0.988 -0.561
11 C18 C C7 N N N 0 3.567 1.366 -1.989
12 C19 C C8 N N N 0 4.522 1.828 -2.757
13 C2 C C16 N Y N 0 -2.175 0.673 0.55
14 C3 C C15 N Y N 0 -1.94 -0.618 0.052
15 C4 C C11 N Y N 0 -0.748 -1.309 0.341
16 C5 C C12 N Y N 0 -0.591 -2.565 -0.172
17 C6 C C13 N Y N 0 -1.593 -3.124 -0.962
18 C7 C C14 N Y N 0 -2.917 -1.244 -0.762
19 C8 C C17 N Y N 0 -4.107 -0.555 -1.057
20 C9 C C18 N Y N 0 -4.303 0.697 -0.565
21 H1 H H1 N N N 0 1.542 -2.299 1.192
22 H10 H H10 N N N 0 3.652 2.409 1.045
23 H11 H H11 N N N 0 4.92 1.162 -0.35
24 H12 H H12 N N N 0 2.566 1.255 -2.38
25 H13 H H13 N N N 0 5.523 1.939 -2.366
26 H14 H H14 N N N 0 4.309 2.099 -3.78
27 H15 H H15 N N N 0 4.139 -1.116 -0.999
28 H16 H H16 N N N 0 1.779 -1.75 -0.446
29 H17 H H17 N N N 0 1.816 -0.438 -1.652
30 H18 H H18 N N N 0 0.31 -3.124 0.034
31 H19 H H19 N N N 0 -1.454 -4.118 -1.361
32 H2 H H2 N N N 0 -0.144 -0.066 1.967
33 H20 H H20 N N N 0 -1.435 1.159 1.168
34 H21 H H21 N N N 0 -4.863 -1.02 -1.673
35 H22 H H22 N N N 0 -5.219 1.221 -0.795
36 H23 H H23 N N N 0 -4.882 3.261 -0.707
37 H24 H H24 N N N 0 -5.638 2.564 0.746
38 H25 H H25 N N N 0 -4.867 4.167 0.825
39 H3 H H3 N N N 0 0.619 0.877 -0.257
40 H5 H H5 N N N 0 3.601 0.642 2.67
41 H6 H H6 N N N 0 2.296 -0.568 2.631
42 H7 H H7 N N N 0 4.867 -0.681 1.345
43 H8 H H8 N N N 0 3.559 -1.891 1.304
44 H9 H H9 N N N 0 2.384 2.512 -0.201
45 N N N2 N Y N 0 -2.7 -2.476 -1.233
46 N1 N N1 S N N 0 2.148 0.949 1.184
47 O O O2 N N N 0 -3.572 2.56 0.728
48 O1 O O1 N N N 0 1.098 -1.711 1.818



QI9 : Chemical Bonds

Total Number of Bonds: 51
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C16 N1 C N sing 1.47 N N
2 C16 C17 C C sing 1.53 N N
3 N1 C15 N C sing 1.47 N N
4 N1 C11 N C sing 1.47 N N
5 C15 C14 C C sing 1.53 N N
6 C17 C18 C C sing 1.51 N N
7 C17 C13 C C sing 1.53 N N
8 O C O C sing 1.43 N N
9 O C1 O C sing 1.36 N N
10 C19 C18 C C doub 1.31 N N
11 C14 C13 C C sing 1.53 N N
12 C11 C10 C C sing 1.53 N N
13 C11 C12 C C sing 1.53 N N
14 C13 C12 C C sing 1.53 N N
15 C1 C2 C C doub 1.37 N Y
16 C1 C9 C C sing 1.4 N Y
17 C2 C3 C C sing 1.4 N Y
18 C10 O1 C O sing 1.43 N N
19 C10 C4 C C sing 1.51 N N
20 C9 C8 C C doub 1.36 N Y
21 C3 C4 C C doub 1.41 N Y
22 C3 C7 C C sing 1.42 N Y
23 C4 C5 C C sing 1.37 N Y
24 C8 C7 C C sing 1.41 N Y
25 C7 N C N doub 1.34 N Y
26 C5 C6 C C doub 1.39 N Y
27 N C6 N C sing 1.31 N Y
28 O1 H1 O H sing 0.97 N N
29 C10 H2 C H sing 1.09 N N
30 C11 H3 C H sing 1.09 N N
31 C15 H5 C H sing 1.09 N N
32 C15 H6 C H sing 1.09 N N
33 C14 H7 C H sing 1.09 N N
34 C14 H8 C H sing 1.09 N N
35 C16 H9 C H sing 1.09 N N
36 C16 H10 C H sing 1.09 N N
37 C17 H11 C H sing 1.09 N N
38 C18 H12 C H sing 1.08 N N
39 C19 H13 C H sing 1.08 N N
40 C19 H14 C H sing 1.08 N N
41 C13 H15 C H sing 1.09 N N
42 C12 H16 C H sing 1.09 N N
43 C12 H17 C H sing 1.09 N N
44 C5 H18 C H sing 1.08 N N
45 C6 H19 C H sing 1.08 N N
46 C2 H20 C H sing 1.08 N N
47 C8 H21 C H sing 1.08 N N
48 C9 H22 C H sing 1.08 N N
49 C H23 C H sing 1.09 N N
50 C H24 C H sing 1.09 N N
51 C H25 C H sing 1.09 N N



QI9 : Used in PDB Entries

Total Number of PDB Entries: 4
Ligand Code PDB Entry ID Type Total Distinct
QI9 4uil Open in New Window Bound ligand 1 1
QI9 4uin Open in New Window Bound ligand 1 1
QI9 4wnv Open in New Window Bound ligand 4 1
QI9 5znc Open in New Window Bound ligand 1 1