Chemical Components in the PDB

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4KE : Summary

Code

4KE

One-letter code

X

Molecule name

(3R,4S,5R)-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohex-1-ene-1-carboxylic acid

Systematic names

ProgramVersionName
ACDLabs 12.01 (3R,4S,5R)-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohex-1-ene-1-carboxylic acid
OpenEye OEToolkits 1.7.6 (3R,4S,5R)-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-3,4-bis(oxidanyl)cyclohexene-1-carboxylic acid

Formula

C16 H16 O7

Formal charge

0

Molecular weight

320.294 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=C(O)C2=CC(O)C(O)C(OC(=O)\C=C\c1ccc(O)cc1)C2
SMILES CACTVS 3.370 O[CH]1C=C(C[CH](OC(=O)C=Cc2ccc(O)cc2)[CH]1O)C(O)=O
SMILES OpenEye OEToolkits 1.7.6 c1cc(ccc1C=CC(=O)OC2CC(=CC(C2O)O)C(=O)O)O
Canonical SMILES CACTVS 3.370 O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\c2ccc(O)cc2)[C@H]1O)C(O)=O
Canonical SMILES OpenEye OEToolkits 1.7.6 c1cc(ccc1/C=C/C(=O)O[C@@H]2CC(=C[C@H]([C@@H]2O)O)C(=O)O)O

IUPAC InChI

InChI=1S/C16H16O7/c17-11-4-1-9(2-5-11)3-6-14(19)23-13-8-10(16(21)22)7-12(18)15(13)20/h1-7,12-13,15,17-18,20H,8H2,(H,21,22)/b6-3+/t12-,13-,15+/m1/s1

IUPAC InChI key

GVECSFFLZYNEBO-ADMZAUMBSA-N
4KE

wwPDB Information

Atom count

39 (23 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2013-04-30

Last modified at

2013-05-17

Status

Released

Obsoleted

Not Assigned



4KE : Atoms of Molecule

Total Number of Atoms: 39
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C01 C C01 N N N 0 2.571 0.621 -0.445
2 C02 C C02 R N N 0 1.936 -0.65 0.124
3 C03 C C03 S N N 0 2.741 -1.859 -0.368
4 C04 C C04 R N N 0 4.123 -1.822 0.289
5 C05 C C05 N N N 0 4.736 -0.461 0.127
6 C06 C C06 N N N 0 4.051 0.617 -0.193
7 C07 C C07 N N N 0 4.777 1.889 -0.31
8 O08 O O08 N N N 0 4.113 3.016 -0.635
9 O09 O O09 N N N 0 5.975 1.925 -0.112
10 O10 O O10 N N N 0 3.994 -2.121 1.68
11 O11 O O11 N N N 0 2.883 -1.795 -1.789
12 O12 O O12 N N N 0 0.585 -0.756 -0.33
13 C13 C C13 N N N 0 -0.366 -0.184 0.438
14 C14 C C14 N N N 0 -1.727 -0.252 0.048
15 C15 C C15 N N N 0 -2.679 0.32 0.817
16 C16 C C16 N Y N 0 -4.09 0.251 0.412
17 O17 O O17 N N N 0 -0.055 0.388 1.465
18 C18 C C18 N Y N 0 -5.079 0.843 1.207
19 C19 C C19 N Y N 0 -6.399 0.775 0.824
20 C20 C C20 N Y N 0 -6.752 0.119 -0.351
21 C21 C C21 N Y N 0 -5.774 -0.47 -1.144
22 C22 C C22 N Y N 0 -4.45 -0.403 -0.773
23 O23 O O23 N N N 0 -8.055 0.054 -0.724
24 H1 H H1 N N N 0 2.388 0.667 -1.519
25 H2 H H2 N N N 0 2.127 1.493 0.035
26 H3 H H3 N N N 0 1.955 -0.612 1.213
27 H4 H H4 N N N 0 2.226 -2.779 -0.092
28 H5 H H5 N N N 0 4.767 -2.564 -0.183
29 H6 H H6 N N N 0 5.8 -0.36 0.282
30 H7 H H7 N N N 0 4.633 3.829 -0.7
31 H8 H H8 N N N 0 4.832 -2.116 2.162
32 H9 H H9 N N N 0 3.384 -2.531 -2.167
33 H10 H H10 N N N 0 -2.003 -0.76 -0.864
34 H11 H H11 N N N 0 -2.403 0.829 1.729
35 H12 H H12 N N N 0 -4.806 1.352 2.12
36 H13 H H13 N N N 0 -7.163 1.231 1.436
37 H14 H H14 N N N 0 -6.053 -0.978 -2.055
38 H15 H H15 N N N 0 -3.691 -0.861 -1.39
39 H16 H H16 N N N 0 -8.342 0.791 -1.281



4KE : Chemical Bonds

Total Number of Bonds: 40
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 O09 C07 O C doub 1.21 N N
2 O08 C07 O C sing 1.35 N N
3 C07 C06 C C sing 1.47 N N
4 C06 C01 C C sing 1.5 N N
5 C06 C05 C C doub 1.32 N N
6 C01 C02 C C sing 1.53 N N
7 C05 C04 C C sing 1.5 N N
8 C02 O12 C O sing 1.43 N N
9 C02 C03 C C sing 1.53 N N
10 O12 C13 O C sing 1.35 N N
11 C04 C03 C C sing 1.53 N N
12 C04 O10 C O sing 1.43 N N
13 C03 O11 C O sing 1.43 N N
14 C13 C14 C C sing 1.42 N N
15 C13 O17 C O doub 1.22 N N
16 C14 C15 C C doub 1.35 E N
17 C22 C21 C C doub 1.38 N Y
18 C22 C16 C C sing 1.4 N Y
19 C21 C20 C C sing 1.39 N Y
20 C15 C16 C C sing 1.47 N N
21 C16 C18 C C doub 1.4 N Y
22 C20 O23 C O sing 1.36 N N
23 C20 C19 C C doub 1.39 N Y
24 C18 C19 C C sing 1.38 N Y
25 C01 H1 C H sing 1.09 N N
26 C01 H2 C H sing 1.09 N N
27 C02 H3 C H sing 1.09 N N
28 C03 H4 C H sing 1.09 N N
29 C04 H5 C H sing 1.09 N N
30 C05 H6 C H sing 1.08 N N
31 O08 H7 O H sing 0.97 N N
32 O10 H8 O H sing 0.97 N N
33 O11 H9 O H sing 0.97 N N
34 C14 H10 C H sing 1.08 N N
35 C15 H11 C H sing 1.08 N N
36 C18 H12 C H sing 1.08 N N
37 C19 H13 C H sing 1.08 N N
38 C21 H14 C H sing 1.08 N N
39 C22 H15 C H sing 1.08 N N
40 O23 H16 O H sing 0.97 N N



4KE : Used in PDB Entries

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