Chemical Components in the PDB

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LCL : Summary

Code

LCL

One-letter code

X

Molecule name

2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide

Synonyms

L-Chloramphenicol

Systematic names

ProgramVersionName
ACDLabs 12.01 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
OpenEye OEToolkits 1.7.6 2,2-bis(chloranyl)-N-[(1S,2S)-1-(4-nitrophenyl)-1,3-bis(oxidanyl)propan-2-yl]ethanamide

Formula

C11 H12 Cl2 N2 O5

Formal charge

0

Molecular weight

323.129 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=[N+]([O-])c1ccc(cc1)C(O)C(NC(=O)C(Cl)Cl)CO
SMILES CACTVS 3.370 OC[CH](NC(=O)C(Cl)Cl)[CH](O)c1ccc(cc1)[N+]([O-])=O
SMILES OpenEye OEToolkits 1.7.6 c1cc(ccc1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
Canonical SMILES CACTVS 3.370 OC[C@H](NC(=O)C(Cl)Cl)[C@@H](O)c1ccc(cc1)[N+]([O-])=O
Canonical SMILES OpenEye OEToolkits 1.7.6 c1cc(ccc1[C@@H]([C@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

IUPAC InChI

InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m0/s1

IUPAC InChI key

WIIZWVCIJKGZOK-IUCAKERBSA-N
LCL

wwPDB Information

Atom count

32 (20 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2012-08-16

Last modified at

2021-03-01

Status

Released

Obsoleted

Not Assigned



LCL : Atoms of Molecule

Total Number of Atoms: 32
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 -2.378 -1.632 0.162
2 CL1 CL CL1 N N N 0 -3.359 -1.104 1.579
3 CL2 CL CL2 N N N 0 -3.368 -2.716 -0.885
4 C2 C C2 N N N 0 -1.949 -0.423 -0.63
5 O2 O O2 N N N 0 -2.205 -0.352 -1.814
6 N2 N N2 N N N 0 -1.281 0.578 -0.024
7 C3 C C3 S N N 0 -0.864 1.752 -0.794
8 C4 C C4 N N N 0 -2.017 2.756 -0.857
9 O4 O O4 N N N 0 -2.295 3.245 0.457
10 C5 C C5 S N N 0 0.343 2.404 -0.117
11 O5 O O5 N N N 0 -0.012 2.804 1.208
12 C6 C C6 N Y N 0 1.479 1.415 -0.055
13 C7 C C7 N Y N 0 2.503 1.48 -0.98
14 C8 C C8 N Y N 0 3.545 0.573 -0.924
15 C9 C C9 N Y N 0 3.562 -0.4 0.059
16 N9 N N9 N N N 1 4.676 -1.371 0.119
17 O9A O O9A N N N -1 5.579 -1.314 -0.697
18 O9B O O9B N N N 0 4.692 -2.228 0.985
19 C10 C C10 N Y N 0 2.538 -0.464 0.985
20 C11 C C11 N Y N 0 1.498 0.446 0.931
21 H1 H H1 N N N 0 -1.496 -2.169 0.51
22 H2 H H2 N N N 0 -1.076 0.521 0.923
23 H3 H H3 N N N 0 -0.593 1.447 -1.804
24 H4 H H4 N N N 0 -1.739 3.589 -1.503
25 H5 H H5 N N N 0 -2.904 2.266 -1.258
26 H6 H H6 N N N 0 -3.017 3.887 0.493
27 H7 H H7 N N N 0 0.653 3.278 -0.689
28 H8 H H8 N N N 0 -0.299 2.076 1.776
29 H9 H H9 N N N 0 2.49 2.239 -1.748
30 H10 H H10 N N N 0 4.345 0.623 -1.647
31 H13 H H13 N N N 0 2.551 -1.223 1.753
32 H14 H H14 N N N 0 0.698 0.396 1.655



LCL : Chemical Bonds

Total Number of Bonds: 32
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 CL1 C1 CL C sing 1.8 N N
2 C1 CL2 C CL sing 1.8 N N
3 C1 C2 C C sing 1.51 N N
4 C2 O2 C O doub 1.21 N N
5 C2 N2 C N sing 1.35 N N
6 N2 C3 N C sing 1.46 N N
7 C4 C3 C C sing 1.53 N N
8 C4 O4 C O sing 1.43 N N
9 C3 C5 C C sing 1.53 N N
10 C11 C10 C C doub 1.38 N Y
11 C11 C6 C C sing 1.38 N Y
12 C10 C9 C C sing 1.38 N Y
13 C5 C6 C C sing 1.51 N N
14 C5 O5 C O sing 1.43 N N
15 C6 C7 C C doub 1.38 N Y
16 O9B N9 O N doub 1.22 N N
17 C9 N9 C N sing 1.48 N N
18 C9 C8 C C doub 1.38 N Y
19 C7 C8 C C sing 1.38 N Y
20 N9 O9A N O sing 1.22 N N
21 C1 H1 C H sing 1.09 N N
22 N2 H2 N H sing 0.97 N N
23 C3 H3 C H sing 1.09 N N
24 C4 H4 C H sing 1.09 N N
25 C4 H5 C H sing 1.09 N N
26 O4 H6 O H sing 0.97 N N
27 C5 H7 C H sing 1.09 N N
28 O5 H8 O H sing 0.97 N N
29 C7 H9 C H sing 1.08 N N
30 C8 H10 C H sing 1.08 N N
31 C10 H13 C H sing 1.08 N N
32 C11 H14 C H sing 1.08 N N



LCL : Used in PDB Entries

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