Chemical Components in the PDB

pdbe.org/chem
wwPDB
EMDataBank
spacer

9EC : Summary

Code

9EC

One-letter code

X

Molecule name

(1R,2R,4S,5S,7s)-7-({[4-fluoro-2-(thiophen-2-yl)phenyl]carbamoyl}oxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]nonan-9-ium

Systematic names

ProgramVersionName
ACDLabs 12.01 (1R,2R,4S,5S,7s)-7-({[4-fluoro-2-(thiophen-2-yl)phenyl]carbamoyl}oxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]nonan-9-ium
OpenEye OEToolkits 2.0.6 [(1~{S},2~{S},4~{R},5~{R})-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.0^{2,4}]nonan-7-yl] ~{N}-(4-fluoranyl-2-thiophen-2-yl-phenyl)carbamate

Formula

C20 H22 F N2 O3 S

Formal charge

1

Molecular weight

389.464 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 c1(cc(ccc1NC(=O)OC2CC3C4C(C(C2)[N+]3(C)C)O4)F)c5cccs5
SMILES CACTVS 3.385 C[N+]1(C)[CH]2C[CH](C[CH]1[CH]3O[CH]23)OC(=O)Nc4ccc(F)cc4c5sccc5
SMILES OpenEye OEToolkits 2.0.6 C[N+]1(C2CC(CC1C3C2O3)OC(=O)Nc4ccc(cc4c5cccs5)F)C
Canonical SMILES CACTVS 3.385 C[N+]1(C)[C@H]2C[C@@H](C[C@@H]1[C@H]3O[C@@H]23)OC(=O)Nc4ccc(F)cc4c5sccc5
Canonical SMILES OpenEye OEToolkits 2.0.6 C[N+]1([C@@H]2CC(C[C@H]1[C@H]3[C@@H]2O3)OC(=O)Nc4ccc(cc4c5cccs5)F)C

IUPAC InChI

InChI=1S/C20H21FN2O3S/c1-23(2)15-9-12(10-16(23)19-18(15)26-19)25-20(24)22-14-6-5-11(21)8-13(14)17-4-3-7-27-17/h3-8,12,15-16,18-19H,9-10H2,1-2H3/p+1/t12-,15-,16+,18-,19+

IUPAC InChI key

YBYUWXNCRPKGOH-ADYDWEGLSA-O
9EC

wwPDB Information

Atom count

49 (27 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2018-03-22

Last modified at

2018-11-23

Status

Released

Obsoleted

Not Assigned



9EC : Atoms of Molecule

Total Number of Atoms: 49
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C10 C C1 N Y N 0 -3.293 -0.116 -0.157
2 C11 C C2 N Y N 0 -3.271 1.358 -0.068
3 C12 C C3 N Y N 0 -3.908 2.199 -0.908
4 C13 C C4 N Y N 0 -3.738 3.538 -0.623
5 C14 C C5 N Y N 0 -2.97 3.797 0.439
6 C02 C C6 N N N 0 0.192 -0.808 0.537
7 C04 C C7 N Y N 0 -2.096 -0.843 -0.114
8 C05 C C8 N Y N 0 -2.127 -2.227 -0.191
9 C06 C C9 N Y N 0 -3.336 -2.887 -0.311
10 C07 C C10 N Y N 0 -4.523 -2.172 -0.355
11 C09 C C11 N Y N 0 -4.507 -0.793 -0.278
12 C17 C C12 S N N 0 2.499 -0.948 1.134
13 C18 C C13 N N N 0 3.18 -1.79 0.051
14 C19 C C14 S N N 0 3.841 -0.85 -0.969
15 C20 C C15 S N N 0 2.807 0.235 -1.352
16 C21 C C16 R N N 0 3.01 1.358 -0.313
17 C24 C C17 N N N 0 5.759 0.625 -1.204
18 C25 C C18 N N N 0 5.713 -1.011 0.572
19 C26 C C19 R N N 0 4.135 0.842 0.613
20 C27 C C20 N N N 0 3.509 0.033 1.737
21 F08 F F1 N N N 0 -5.698 -2.827 -0.472
22 N03 N N1 N N N 0 -0.873 -0.174 0.007
23 N23 N N2 N N N 1 4.907 -0.101 -0.252
24 O01 O O1 N N N 0 0.065 -1.921 1.007
25 O16 O O2 N N N 0 1.397 -0.206 0.547
26 O22 O O3 N N N 0 3.295 1.531 -1.703
27 S15 S S1 N Y N 0 -2.414 2.29 1.153
28 H37 H H1 N N N 0 -4.504 1.851 -1.739
29 H38 H H2 N N N 0 -4.192 4.319 -1.214
30 H39 H H3 N N N 0 -2.73 4.784 0.806
31 H34 H H4 N N N 0 -1.206 -2.789 -0.159
32 H35 H H5 N N N 0 -3.355 -3.965 -0.372
33 H36 H H6 N N N 0 -5.434 -0.239 -0.308
34 H28 H H7 N N N 0 2.118 -1.604 1.917
35 H40 H H8 N N N 0 3.939 -2.426 0.507
36 H41 H H9 N N N 0 2.437 -2.411 -0.45
37 H29 H H10 N N N 0 4.216 -1.387 -1.84
38 H30 H H11 N N N 0 1.829 -0.093 -1.704
39 H31 H H12 N N N 0 2.178 1.894 0.143
40 H43 H H13 N N N 0 6.193 -0.079 -1.914
41 H42 H H14 N N N 0 5.158 1.36 -1.741
42 H44 H H15 N N N 0 6.556 1.134 -0.663
43 H45 H H16 N N N 0 6.504 -0.448 1.068
44 H46 H H17 N N N 0 5.077 -1.481 1.322
45 H47 H H18 N N N 0 6.156 -1.779 -0.062
46 H32 H H19 N N N 0 4.754 1.657 0.989
47 H49 H H20 N N N 0 2.998 0.704 2.427
48 H48 H H21 N N N 0 4.283 -0.521 2.268
49 H33 H H22 N N N 0 -0.792 0.746 -0.29



9EC : Chemical Bonds

Total Number of Bonds: 53
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C25 N23 C N sing 1.47 N N
2 C24 N23 C N sing 1.47 N N
3 N23 C19 N C sing 1.49 N N
4 N23 C26 N C sing 1.49 N N
5 C19 C18 C C sing 1.54 N N
6 C19 C20 C C sing 1.55 N N
7 C18 C17 C C sing 1.53 N N
8 C20 O22 C O sing 1.43 N N
9 C20 C21 C C sing 1.54 N N
10 C26 C27 C C sing 1.52 N N
11 C26 C21 C C sing 1.55 N N
12 C17 C27 C C sing 1.53 N N
13 C17 O16 C O sing 1.45 N N
14 O22 C21 O C sing 1.43 N N
15 O01 C02 O C doub 1.21 N N
16 O16 C02 O C sing 1.35 N N
17 C14 C13 C C doub 1.34 N Y
18 C14 S15 C S sing 1.76 N Y
19 C02 N03 C N sing 1.35 N N
20 C13 C12 C C sing 1.38 N Y
21 S15 C11 S C sing 1.76 N Y
22 N03 C04 N C sing 1.4 N N
23 C12 C11 C C doub 1.35 N Y
24 C11 C10 C C sing 1.48 N N
25 C04 C10 C C doub 1.4 N Y
26 C04 C05 C C sing 1.39 N Y
27 C10 C09 C C sing 1.4 N Y
28 C05 C06 C C doub 1.38 N Y
29 C09 C07 C C doub 1.38 N Y
30 C06 C07 C C sing 1.39 N Y
31 C07 F08 C F sing 1.35 N N
32 C12 H37 C H sing 1.08 N N
33 C13 H38 C H sing 1.08 N N
34 C14 H39 C H sing 1.08 N N
35 C05 H34 C H sing 1.08 N N
36 C06 H35 C H sing 1.08 N N
37 C09 H36 C H sing 1.08 N N
38 C17 H28 C H sing 1.09 N N
39 C18 H40 C H sing 1.09 N N
40 C18 H41 C H sing 1.09 N N
41 C19 H29 C H sing 1.09 N N
42 C20 H30 C H sing 1.09 N N
43 C21 H31 C H sing 1.09 N N
44 C24 H43 C H sing 1.09 N N
45 C24 H42 C H sing 1.09 N N
46 C24 H44 C H sing 1.09 N N
47 C25 H45 C H sing 1.09 N N
48 C25 H46 C H sing 1.09 N N
49 C25 H47 C H sing 1.09 N N
50 C26 H32 C H sing 1.09 N N
51 C27 H49 C H sing 1.09 N N
52 C27 H48 C H sing 1.09 N N
53 N03 H33 N H sing 0.97 N N



9EC : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
9EC 5zhp Open in New Window Bound ligand 2 1