Chemical Components in the PDB

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KEF : Summary

Code

KEF

One-letter code

X

Molecule name

CEFUROXIME (OCT-3-ENE FORM)

Systematic names

ProgramVersionName
ACDLabs 10.04 (2R,6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid
OpenEye OEToolkits 1.5.0 (6R,7R)-3-(aminocarbonyloxymethyl)-7-[[2-(furan-2-yl)-2-methoxyimino-ethanoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Formula

C16 H16 N4 O8 S

Formal charge

0

Molecular weight

424.385 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 10.04 O=C2N1C(C(=CSC1C2NC(=O)C(=N\OC)/c3occc3)COC(=O)N)C(=O)O
SMILES CACTVS 3.341 CON=C(C(=O)N[CH]1[CH]2SC=C(COC(N)=O)[CH](N2C1=O)C(O)=O)c3occc3
SMILES OpenEye OEToolkits 1.5.0 CON=C(c1ccco1)C(=O)NC2C3N(C2=O)C(C(=CS3)COC(=O)N)C(=O)O
Canonical SMILES CACTVS 3.341 CO\N=C(C(=O)N[C@H]1[C@H]2SC=C(COC(N)=O)[C@@H](N2C1=O)C(O)=O)\c3occc3
Canonical SMILES OpenEye OEToolkits 1.5.0 CON=C(c1ccco1)C(=O)N[C@H]2[C@@H]3N(C2=O)C(C(=CS3)COC(=O)N)C(=O)O

IUPAC InChI

InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,6,10-11,14H,5H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,11-,14-/m1/s1

IUPAC InChI key

AIEMBSSBMKFDGU-HPUGUEDKSA-N
KEF

wwPDB Information

Atom count

45 (29 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

1999-10-06

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



KEF : Atoms of Molecule

Total Number of Atoms: 45
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C14 C C14 N Y N 0 3.55 1.822 -0.119
2 O15 O O15 N Y N 0 2.256 2.151 0.062
3 C16 C C16 N Y N 0 2.118 3.483 -0.025
4 C17 C C17 N Y N 0 3.328 4.029 -0.265
5 C19 C C19 N Y N 0 4.255 2.972 -0.321
6 C18 C C18 N N N 0 7.338 -0.904 -0.421
7 O17 O O17 N N N 0 5.939 -1.024 -0.158
8 N16 N N16 N N N 0 5.385 0.273 -0.286
9 C4' C C4' N N N 0 -3.174 -2.596 0.076
10 C3' C C3' N N N 0 -4.186 0.206 -0.553
11 C11 C C11 N N N 0 3.217 -0.702 0.142
12 C13 C C13 N N N 0 4.108 0.459 -0.096
13 C2 C C2 N N N 0 -2.181 0.706 0.612
14 C3 C C3 N N N 0 -2.798 -0.174 -0.103
15 C4 C C4 R N N 0 -2.318 -1.524 -0.546
16 C6 C C6 R N N 0 -0.328 -1.221 1.179
17 C7 C C7 R N N 0 1.014 -1.648 0.576
18 C8 C C8 N N N 0 0.228 -2.198 -0.599
19 N10 N N10 N N N 0 1.884 -0.523 0.225
20 N5 N N5 N N N 0 -0.925 -1.703 -0.107
21 O4A O O4A N N N 0 -4.494 -2.627 -0.17
22 O4B O O4B N N N 0 -2.674 -3.427 0.796
23 O12 O O12 N N N 0 3.689 -1.815 0.262
24 O9 O O9 N N N 0 0.523 -2.812 -1.603
25 S1 S S1 N N N 0 -0.554 0.583 1.266
26 O3' O O3' N N N 0 -4.511 1.53 -0.052
27 C31 C C31 N N N 0 -5.708 2.079 -0.331
28 O31 O O31 N N N 0 -6.516 1.468 -1.002
29 N31 N N31 N N N 0 -6.01 3.308 0.134
30 H16 H H16 N N N 0 1.191 4.028 0.079
31 H17 H H17 N N N 0 3.546 5.08 -0.386
32 H19 H H19 N N N 0 5.317 3.054 -0.496
33 H183 H 3H18 N N N 0 7.486 -0.518 -1.43
34 H182 H 2H18 N N N 0 7.809 -1.883 -0.334
35 H181 H 1H18 N N N 0 7.786 -0.219 0.299
36 H3'2 H 2H3' N N N 0 -4.904 -0.516 -0.164
37 H3'1 H 1H3' N N N 0 -4.226 0.21 -1.642
38 H2 H H2 N N N 0 -2.722 1.614 0.833
39 H4 H H4 N N N 0 -2.374 -1.594 -1.633
40 H6 H H6 N N N 0 -0.633 -1.758 2.077
41 H7 H H7 N N N 0 1.528 -2.415 1.155
42 H10 H H10 N N N 0 1.5 0.351 0.052
43 H4O H H4O N N N 0 -5.044 -3.315 0.23
44 HN31 H 1HN3 N N N 0 -5.366 3.796 0.67
45 HN32 H 2HN3 N N N 0 -6.873 3.704 -0.067



KEF : Chemical Bonds

Total Number of Bonds: 47
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C14 O15 C O sing 1.35 N Y
2 C14 C19 C C doub 1.36 N Y
3 C14 C13 C C sing 1.47 N N
4 O15 C16 O C sing 1.34 N Y
5 C16 C17 C C doub 1.35 N Y
6 C16 H16 C H sing 1.08 N N
7 C17 C19 C C sing 1.41 N Y
8 C17 H17 C H sing 1.08 N N
9 C19 H19 C H sing 1.08 N N
10 C18 O17 C O sing 1.43 N N
11 C18 H183 C H sing 1.09 N N
12 C18 H182 C H sing 1.09 N N
13 C18 H181 C H sing 1.09 N N
14 O17 N16 O N sing 1.42 N N
15 N16 C13 N C doub 1.3 E N
16 C4' C4 C C sing 1.51 N N
17 C4' O4A C O sing 1.34 N N
18 C4' O4B C O doub 1.21 N N
19 C3' C3 C C sing 1.51 N N
20 C3' O3' C O sing 1.45 N N
21 C3' H3'2 C H sing 1.09 N N
22 C3' H3'1 C H sing 1.09 N N
23 C11 C13 C C sing 1.48 N N
24 C11 N10 C N sing 1.35 N N
25 C11 O12 C O doub 1.21 N N
26 C2 C3 C C doub 1.29 N N
27 C2 S1 C S sing 1.76 N N
28 C2 H2 C H sing 1.08 N N
29 C3 C4 C C sing 1.5 N N
30 C4 N5 C N sing 1.47 N N
31 C4 H4 C H sing 1.09 N N
32 C6 C7 C C sing 1.53 N N
33 C6 N5 C N sing 1.5 N N
34 C6 S1 C S sing 1.82 N N
35 C6 H6 C H sing 1.09 N N
36 C7 C8 C C sing 1.52 N N
37 C7 N10 C N sing 1.46 N N
38 C7 H7 C H sing 1.09 N N
39 C8 N5 C N sing 1.35 N N
40 C8 O9 C O doub 1.21 N N
41 N10 H10 N H sing 0.97 N N
42 O4A H4O O H sing 0.97 N N
43 O3' C31 O C sing 1.35 N N
44 C31 O31 C O doub 1.22 N N
45 C31 N31 C N sing 1.35 N N
46 N31 HN31 N H sing 0.97 N N
47 N31 HN32 N H sing 0.97 N N



KEF : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
KEF 1qmf Open in New Window Bound ligand 1 1