Chemical Components in the PDB

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0W3 : Summary

Code

0W3

One-letter code

X

Molecule name

(4R,6S,8S,12R,14R,16Z,18R,19R,20S,21S)-19,21-dihydroxy-22-{(2S,2'R,5S,5'S)-5'-[(1R)-1-hydroxyethyl]-2,5'-dimethyloctahydro-2,2'-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-9,11-dioxodocos-16-enoic acid

Synonyms

Ionomycin

Systematic names

ProgramVersionName
ACDLabs 12.01 (4R,6S,8S,12R,14R,16Z,18R,19R,20S,21S)-19,21-dihydroxy-22-{(2S,2'R,5S,5'S)-5'-[(1R)-1-hydroxyethyl]-2,5'-dimethyloctahydro-2,2'-bifuran-5-yl}-4,6,8,12,14,18,20-heptamethyl-9,11-dioxodocos-16-enoic acid
OpenEye OEToolkits 1.7.6 (Z,4R,6S,8S,12R,14R,18R,19R,20S,21S)-4,6,8,12,14,18,20-heptamethyl-22-[(2S,5S)-5-methyl-5-[(2R,5S)-5-methyl-5-[(1R)-1-oxidanylethyl]oxolan-2-yl]oxolan-2-yl]-19,21-bis(oxidanyl)-9,11-bis(oxidanylidene)docos-16-enoic acid

Formula

C41 H72 O9

Formal charge

0

Molecular weight

709.005 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=C(O)CCC(C)CC(C)CC(C(=O)CC(=O)C(C)CC(C)C/C=C\C(C)C(O)C(C)C(O)CC2OC(C1OC(CC1)(C(O)C)C)(C)CC2)C
SMILES CACTVS 3.370 C[CH](CCC(O)=O)C[CH](C)C[CH](C)C(=O)CC(=O)[CH](C)C[CH](C)CC=C[CH](C)[CH](O)[CH](C)[CH](O)C[CH]1CC[C](C)(O1)[CH]2CC[C](C)(O2)[CH](C)O
SMILES OpenEye OEToolkits 1.7.6 CC(CCC(=O)O)CC(C)CC(C)C(=O)CC(=O)C(C)CC(C)CC=CC(C)C(C(C)C(CC1CCC(O1)(C)C2CCC(O2)(C)C(C)O)O)O
Canonical SMILES CACTVS 3.370 C[C@H](CCC(O)=O)C[C@H](C)C[C@H](C)C(=O)CC(=O)[C@H](C)C[C@H](C)C\C=C/[C@@H](C)[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H]1CC[C@](C)(O1)[C@H]2CC[C@](C)(O2)[C@@H](C)O
Canonical SMILES OpenEye OEToolkits 1.7.6 C[C@H](CCC(=O)O)C[C@H](C)C[C@H](C)C(=O)CC(=O)[C@H](C)C[C@H](C)C/C=C\[C@@H](C)[C@H]([C@@H](C)[C@H](C[C@@H]1CC[C@@](O1)(C)[C@H]2CC[C@@](O2)(C)[C@@H](C)O)O)O

IUPAC InChI

InChI=1S/C41H72O9/c1-25(21-29(5)34(43)24-35(44)30(6)22-27(3)20-26(2)14-15-38(46)47)12-11-13-28(4)39(48)31(7)36(45)23-33-16-18-41(10,49-33)37-17-19-40(9,50-37)32(8)42/h11,13,25-33,36-37,39,42,45,48H,12,14-24H2,1-10H3,(H,46,47)/b13-11-/t25-,26-,27+,28-,29-,30+,31+,32-,33+,36+,37-,39-,40+,41+/m1/s1

IUPAC InChI key

OQWWWMDCZGMEFT-PUAVNTAHSA-N
0W3

wwPDB Information

Atom count

122 (50 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2012-07-17

Last modified at

2013-03-15

Status

Released

Obsoleted

Not Assigned



0W3 : Atoms of Molecule

Total Number of Atoms: 122
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C10 C C10 N N N 0 3.441 1.922 -1.195
2 C11 C C11 R N N 0 7.413 4.062 -0.508
3 C12 C C12 N N N 0 1.452 -1.543 0.469
4 C13 C C13 N N N 0 7.771 2.793 1.624
5 C14 C C14 S N N 0 2.169 -2.863 0.182
6 C15 C C15 N N N 0 7.116 5.295 0.348
7 C16 C C16 S N N 0 1.145 -3.915 -0.25
8 C17 C C17 R N N 0 1.862 -5.236 -0.537
9 C18 C C18 N N N 0 0.123 -4.123 0.869
10 C19 C C19 R N N 0 0.863 -6.245 -1.108
11 C2 C C2 R N N 0 5.249 1.351 0.44
12 C20 C C20 N N N 0 0.19 -5.655 -2.32
13 C21 C C21 N N N 0 1.602 -7.524 -1.507
14 C22 C C22 N N N 0 -1.117 -5.632 -2.398
15 C23 C C23 N N N 0 -1.949 -6.065 -1.219
16 C24 C C24 R N N 0 -2.979 -4.98 -0.895
17 C25 C C25 R N N 0 -4.663 -4.212 0.783
18 C26 C C26 N N N 0 -3.834 -3.029 1.211
19 C27 C C27 N N N 0 -3.381 -0.642 1.605
20 C28 C C28 N N N 0 -3.74 -5.362 0.376
21 C29 C C29 S N N 0 -3.706 0.83 1.615
22 C3 C C3 S N N 0 3.76 1.206 0.119
23 C30 C C30 N N N 0 -4.404 -1.636 1.12
24 C31 C C31 N N N 0 -2.423 1.637 1.407
25 C32 C C32 S N N 0 -2.762 3.128 1.356
26 C33 C C33 N N N 0 -3.963 -4.848 -2.058
27 C34 C C34 N N N 0 -5.553 -4.658 1.945
28 C35 C C35 N N N 0 -3.675 3.403 0.159
29 C36 C C36 N N N 0 -4.332 1.204 2.96
30 C37 C C37 R N N 0 -4.114 4.869 0.179
31 C38 C C38 N N N 0 -1.473 3.939 1.211
32 C39 C C39 N N N 0 -4.924 5.175 -1.082
33 C4 C C4 S N N 0 7.049 2.799 0.275
34 C40 C C40 N N N 0 -4.979 5.125 1.415
35 C41 C C41 N N N 0 -5.257 6.668 -1.124
36 C42 C C42 N N N 0 -6.054 6.97 -2.366
37 C5 C C5 S N N 0 2.455 -0.527 1.02
38 C6 C C6 N N N 0 6.114 0.775 -0.711
39 C7 C C7 N N N 0 2.917 1.808 1.263
40 C8 C C8 N N N 0 7.443 1.549 -0.536
41 C9 C C9 N N N 0 1.739 0.802 1.37
42 H10 H H10 N N N 0 2.362 1.928 -1.353
43 H10A H H10A N N N 0 3.807 2.947 -1.149
44 H10B H H10B N N N 0 3.926 1.4 -2.02
45 H11 H H11 N N N 0 6.823 4.105 -1.423
46 H12 H H12 N N N 0 0.664 -1.709 1.203
47 H12A H H12A N N N 0 1.015 -1.158 -0.452
48 H13 H H13 N N N 0 7.5 1.893 2.177
49 H13A H H13A N N N 0 8.848 2.809 1.46
50 H13B H H13B N N N 0 7.477 3.673 2.197
51 H14 H H14 N N N 0 2.68 -3.203 1.083
52 H15 H H15 N N N 0 7.376 6.195 -0.209
53 H15A H H15A N N N 0 6.056 5.317 0.6
54 H15B H H15B N N N 0 7.706 5.252 1.264
55 H16 H H16 N N N 0 0.634 -3.576 -1.151
56 H17 H H17 N N N 0 2.286 -5.628 0.387
57 H18 H H18 N N N 0 0.626 -4.517 1.752
58 H18A H H18A N N N 0 -0.346 -3.17 1.114
59 H18B H H18B N N N 0 -0.639 -4.829 0.539
60 H19 H H19 N N N 0 0.112 -6.479 -0.354
61 H2 H H2 N N N 0 5.489 0.86 1.383
62 H20 H H20 N N N 0 0.786 -5.25 -3.125
63 H21 H H21 N N N 0 2.02 -7.995 -0.617
64 H21A H H21A N N N 0 0.905 -8.211 -1.988
65 H21B H H21B N N N 0 2.406 -7.278 -2.2
66 H22 H H22 N N N 0 -1.599 -5.303 -3.307
67 H23 H H23 N N N 0 -2.465 -6.995 -1.459
68 H23A H H23A N N N 0 -1.303 -6.221 -0.355
69 H24 H H24 N N N 0 -2.468 -4.029 -0.741
70 H25 H H25 N N N 0 -5.288 -3.93 -0.065
71 H28 H H28 N N N 0 -4.334 -6.256 0.189
72 H28A H H28A N N N 0 -3.03 -5.559 1.18
73 H29 H H29 N N N 0 -4.41 1.052 0.812
74 H30 H H30 N N N 0 -4.662 -1.416 0.084
75 H30A H H30A N N N 0 -5.298 -1.569 1.739
76 H31 H H31 N N N 0 -1.737 1.448 2.233
77 H31A H H31A N N N 0 -1.954 1.339 0.47
78 H32 H H32 N N N 0 -3.271 3.417 2.275
79 H33 H H33 N N N 0 -4.639 -4.014 -1.869
80 H33A H H33A N N N 0 -3.413 -4.667 -2.982
81 H33B H H33B N N N 0 -4.539 -5.768 -2.153
82 H34 H H34 N N N 0 -4.929 -5.021 2.762
83 H34A H H34A N N N 0 -6.149 -3.814 2.29
84 H34B H H34B N N N 0 -6.214 -5.458 1.61
85 H35 H H35 N N N 0 -3.134 3.198 -0.765
86 H35A H H35A N N N 0 -4.553 2.76 0.217
87 H36 H H36 N N N 0 -3.655 0.924 3.767
88 H36A H H36A N N N 0 -4.509 2.279 2.991
89 H36B H H36B N N N 0 -5.278 0.676 3.08
90 H37 H H37 N N N 0 -3.234 5.511 0.211
91 H38 H H38 N N N 0 -1.703 5.003 1.277
92 H38A H H38A N N N 0 -0.781 3.667 2.008
93 H38B H H38B N N N 0 -1.016 3.726 0.244
94 H39 H H39 N N N 0 -4.339 4.909 -1.963
95 H39A H H39A N N N 0 -5.848 4.597 -1.071
96 H40 H H40 N N N 0 -4.402 4.907 2.314
97 H40A H H40A N N N 0 -5.292 6.169 1.429
98 H40B H H40B N N N 0 -5.858 4.483 1.383
99 H41 H H41 N N N 0 -5.841 6.935 -0.243
100 H41A H H41A N N N 0 -4.333 7.246 -1.136
101 H5 H H5 N N N 0 2.957 -0.929 1.901
102 H6 H H6 N N N 0 6.267 -0.296 -0.583
103 H6A H H6A N N N 0 5.664 0.989 -1.68
104 H7 H H7 N N N 0 3.487 1.837 2.192
105 H7A H H7A N N N 0 2.559 2.803 0.999
106 H8 H H8 N N N 0 7.848 1.836 -1.506
107 H8A H H8A N N N 0 8.165 0.947 0.018
108 H9 H H9 N N N 0 0.96 1.031 0.642
109 H9A H H9A N N N 0 1.334 0.776 2.381
110 HO2 H HO2 N N N 0 9.105 4.807 -1.335
111 HO3 H HO3 N N N 0 2.738 -2.367 -1.697
112 HO4 H HO4 N N N 0 2.603 -4.665 -2.333
113 HO8 H HO8 N N N 0 -6.969 8.37 -3.424
114 O0 O O0 N N N 0 5.627 2.744 0.481
115 O1 O O1 N N N 0 3.418 -0.181 0.013
116 O2 O O2 N N N 0 8.803 4.034 -0.837
117 O3 O O3 N N N 0 3.124 -2.67 -0.863
118 O4 O O4 N N N 0 2.909 -5.014 -1.485
119 O5 O O5 N N N 0 -2.713 -3.196 1.626
120 O6 O O6 N N N 0 -2.3 -1.024 1.985
121 O7 O O7 N N N 0 -6.328 6.083 -3.139
122 O8 O O8 N N N 0 -6.46 8.225 -2.615



0W3 : Chemical Bonds

Total Number of Bonds: 123
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 O0 C2 O C sing 1.44 N N
2 O0 C4 O C sing 1.44 N N
3 C5 O1 C O sing 1.44 N N
4 O1 C3 O C sing 1.43 N N
5 C3 C2 C C sing 1.53 N N
6 C2 C6 C C sing 1.55 N N
7 C2 H2 C H sing 1.09 N N
8 O2 C11 O C sing 1.43 N N
9 O2 HO2 O H sing 0.97 N N
10 C10 C3 C C sing 1.53 N N
11 C3 C7 C C sing 1.54 N N
12 C14 O3 C O sing 1.43 N N
13 O3 HO3 O H sing 0.97 N N
14 C11 C4 C C sing 1.53 N N
15 C4 C8 C C sing 1.54 N N
16 C4 C13 C C sing 1.53 N N
17 C17 O4 C O sing 1.43 N N
18 O4 HO4 O H sing 0.97 N N
19 C12 C5 C C sing 1.53 N N
20 C5 C9 C C sing 1.55 N N
21 C5 H5 C H sing 1.09 N N
22 C26 O5 C O doub 1.21 N N
23 C6 C8 C C sing 1.55 N N
24 C6 H6 C H sing 1.09 N N
25 C6 H6A C H sing 1.09 N N
26 O6 C27 O C doub 1.21 N N
27 C9 C7 C C sing 1.55 N N
28 C7 H7 C H sing 1.09 N N
29 C7 H7A C H sing 1.09 N N
30 C42 O7 C O doub 1.21 N N
31 C8 H8 C H sing 1.09 N N
32 C8 H8A C H sing 1.09 N N
33 C42 O8 C O sing 1.34 N N
34 O8 HO8 O H sing 0.97 N N
35 C9 H9 C H sing 1.09 N N
36 C9 H9A C H sing 1.09 N N
37 C10 H10 C H sing 1.09 N N
38 C10 H10A C H sing 1.09 N N
39 C10 H10B C H sing 1.09 N N
40 C15 C11 C C sing 1.53 N N
41 C11 H11 C H sing 1.09 N N
42 C14 C12 C C sing 1.53 N N
43 C12 H12 C H sing 1.09 N N
44 C12 H12A C H sing 1.09 N N
45 C13 H13 C H sing 1.09 N N
46 C13 H13A C H sing 1.09 N N
47 C13 H13B C H sing 1.09 N N
48 C16 C14 C C sing 1.53 N N
49 C14 H14 C H sing 1.09 N N
50 C15 H15 C H sing 1.09 N N
51 C15 H15A C H sing 1.09 N N
52 C15 H15B C H sing 1.09 N N
53 C18 C16 C C sing 1.53 N N
54 C16 C17 C C sing 1.53 N N
55 C16 H16 C H sing 1.09 N N
56 C19 C17 C C sing 1.53 N N
57 C17 H17 C H sing 1.09 N N
58 C18 H18 C H sing 1.09 N N
59 C18 H18A C H sing 1.09 N N
60 C18 H18B C H sing 1.09 N N
61 C21 C19 C C sing 1.53 N N
62 C19 C20 C C sing 1.51 N N
63 C19 H19 C H sing 1.09 N N
64 C22 C20 C C doub 1.31 Z N
65 C20 H20 C H sing 1.08 N N
66 C21 H21 C H sing 1.09 N N
67 C21 H21A C H sing 1.09 N N
68 C21 H21B C H sing 1.09 N N
69 C23 C22 C C sing 1.51 N N
70 C22 H22 C H sing 1.08 N N
71 C23 C24 C C sing 1.53 N N
72 C23 H23 C H sing 1.09 N N
73 C23 H23A C H sing 1.09 N N
74 C28 C24 C C sing 1.53 N N
75 C24 C33 C C sing 1.53 N N
76 C24 H24 C H sing 1.09 N N
77 C28 C25 C C sing 1.53 N N
78 C26 C25 C C sing 1.51 N N
79 C25 C34 C C sing 1.53 N N
80 C25 H25 C H sing 1.09 N N
81 C30 C26 C C sing 1.51 N N
82 C29 C27 C C sing 1.51 N N
83 C27 C30 C C sing 1.51 N N
84 C28 H28 C H sing 1.09 N N
85 C28 H28A C H sing 1.09 N N
86 C36 C29 C C sing 1.53 N N
87 C29 C31 C C sing 1.53 N N
88 C29 H29 C H sing 1.09 N N
89 C30 H30 C H sing 1.09 N N
90 C30 H30A C H sing 1.09 N N
91 C31 C32 C C sing 1.53 N N
92 C31 H31 C H sing 1.09 N N
93 C31 H31A C H sing 1.09 N N
94 C38 C32 C C sing 1.53 N N
95 C32 C35 C C sing 1.53 N N
96 C32 H32 C H sing 1.09 N N
97 C33 H33 C H sing 1.09 N N
98 C33 H33A C H sing 1.09 N N
99 C33 H33B C H sing 1.09 N N
100 C34 H34 C H sing 1.09 N N
101 C34 H34A C H sing 1.09 N N
102 C34 H34B C H sing 1.09 N N
103 C35 C37 C C sing 1.53 N N
104 C35 H35 C H sing 1.09 N N
105 C35 H35A C H sing 1.09 N N
106 C36 H36 C H sing 1.09 N N
107 C36 H36A C H sing 1.09 N N
108 C36 H36B C H sing 1.09 N N
109 C37 C40 C C sing 1.53 N N
110 C37 C39 C C sing 1.53 N N
111 C37 H37 C H sing 1.09 N N
112 C38 H38 C H sing 1.09 N N
113 C38 H38A C H sing 1.09 N N
114 C38 H38B C H sing 1.09 N N
115 C39 C41 C C sing 1.53 N N
116 C39 H39 C H sing 1.09 N N
117 C39 H39A C H sing 1.09 N N
118 C40 H40 C H sing 1.09 N N
119 C40 H40A C H sing 1.09 N N
120 C40 H40B C H sing 1.09 N N
121 C41 C42 C C sing 1.51 N N
122 C41 H41 C H sing 1.09 N N
123 C41 H41A C H sing 1.09 N N



0W3 : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
0W3 4fgy Open in New Window Bound ligand 1 1