Chemical Components in the PDB

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0FQ : Summary

Code

0FQ

One-letter code

X

Molecule name

phenacyl coenzyme A

Systematic names

ProgramVersionName
ACDLabs 12.01 [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(2-oxo-2-phenylethyl)sulfanyl]ethyl}amino)propyl]amino}butyl dihydrogen diphosphate (non-preferred name)
OpenEye OEToolkits 1.7.2 [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-oxidanyl-3-phosphonooxy-oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(3R)-2,2-dimethyl-3-oxidanyl-4-oxidanylidene-4-[[3-oxidanylidene-3-(2-phenacylsulfanylethylamino)propyl]amino]butyl] hydrogen phosphate

Formula

C29 H42 N7 O17 P3 S

Formal charge

0

Molecular weight

885.667 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=C(c1ccccc1)CSCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OCC4OC(n3cnc2c(ncnc23)N)C(O)C4OP(=O)(O)O
SMILES CACTVS 3.370 CC(C)(CO[P](O)(=O)O[P](O)(=O)OC[CH]1O[CH]([CH](O)[CH]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[CH](O)C(=O)NCCC(=O)NCCSCC(=O)c4ccccc4
SMILES OpenEye OEToolkits 1.7.2 CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)C(C(=O)NCCC(=O)NCCSCC(=O)c4ccccc4)O
Canonical SMILES CACTVS 3.370 CC(C)(CO[P](O)(=O)O[P](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O[P](O)(O)=O)n2cnc3c(N)ncnc23)[C@@H](O)C(=O)NCCC(=O)NCCSCC(=O)c4ccccc4
Canonical SMILES OpenEye OEToolkits 1.7.2 CC(C)(CO[P@](=O)(O)O[P@@](=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSCC(=O)c4ccccc4)O

IUPAC InChI

InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-20(38)31-10-11-57-13-18(37)17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-12-19-23(52-54(42,43)44)22(39)28(51-19)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,19,22-24,28,39-40H,8-14H2,1-2H3,(H,31,38)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t19-,22-,23-,24+,28-/m1/s1

IUPAC InChI key

WOEFYXMDPBOUAP-VXAHOBLNSA-N
0FQ

wwPDB Information

Atom count

99 (57 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2011-06-10

Last modified at

2014-07-25

Status

Released

Obsoleted

Not Assigned



0FQ : Atoms of Molecule

Total Number of Atoms: 99
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 CB C CB N N N 0 -13.376 -1.73 0.239
2 N1A N N1A N Y N 0 7.343 -7.687 -0.497
3 O1A O O1A N N N 0 5.597 2.795 -2.233
4 P1A P P1A N N N 0 5.099 2.74 -0.841
5 C1B C C1B N N N 0 -14.554 -2.249 1.022
6 O1B O O1B N N N 0 -14.674 -1.967 2.195
7 C1D C C1D R N N 0 7.259 -2.569 0.384
8 S1P S S1P N N N 0 -12.326 -0.723 1.322
9 C2A C C2A N Y N 0 7.413 -7.047 0.655
10 O2A O O2A N N N 0 5.638 4.02 -0.026
11 P2A P P2A N N N 0 2.377 3.532 -1.707
12 C2B C C2B N Y N 0 -15.56 -3.097 0.363
13 C2D C C2D R N N 0 8.721 -2.164 0.673
14 O2D O O2D N N N 0 9.19 -2.798 1.865
15 C2P C C2P N N N 0 -10.986 -0.197 0.219
16 N3A N N3A N Y N 0 7.38 -5.733 0.737
17 O3A O O3A N N N 0 3.489 2.747 -0.847
18 C3B C C3B N Y N 0 -16.654 -3.581 1.086
19 C3D C C3D S N N 0 8.656 -0.632 0.864
20 O3D O O3D N N N 0 9.082 -0.273 2.18
21 P3D P P3D N N N 0 10.318 0.72 2.461
22 C3P C C3P N N N 0 -9.998 0.676 0.995
23 C4A C C4A N Y N 0 7.273 -4.989 -0.359
24 O4A O O4A N N N 0 2.81 4.932 -1.912
25 C4B C C4B N Y N 0 -17.592 -4.376 0.461
26 C4D C C4D R N N 0 7.162 -0.293 0.668
27 O4D O O4D N N N 0 6.641 -1.372 -0.138
28 N4P N N4P N N N 0 -8.916 1.1 0.104
29 C5A C C5A N Y N 0 7.196 -5.623 -1.61
30 O5A O O5A N N N 0 2.196 2.811 -3.135
31 C5B C C5B N Y N 0 -17.452 -4.695 -0.878
32 C5D C C5D N N N 0 7.01 1.041 -0.066
33 O5D O O5D N N N 0 5.627 1.393 -0.134
34 C5P C C5P N N N 0 -7.924 1.882 0.573
35 O5P O O5P N N N 0 -7.927 2.235 1.734
36 C6A C C6A N Y N 0 7.235 -7.027 -1.646
37 N6A N N6A N N N 0 7.163 -7.707 -2.849
38 O6A O O6A N N N 0 0.975 3.514 -0.915
39 C6B C C6B N Y N 0 -16.372 -4.22 -1.601
40 C6P C C6P N N N 0 -6.81 2.319 -0.344
41 N7A N N7A N Y N 0 7.095 -4.648 -2.546
42 O7A O O7A N N N 0 10.096 1.997 1.748
43 C7B C C7B N Y N 0 -15.429 -3.42 -0.992
44 C7P C C7P N N N 0 -5.823 3.192 0.433
45 C8A C C8A N Y N 0 7.106 -3.485 -1.962
46 O8A O O8A N N N 0 10.431 1.001 4.043
47 N8P N N8P N N N 0 -4.74 3.616 -0.459
48 N9A N N9A N Y N 0 7.214 -3.642 -0.613
49 O9A O O9A N N N 0 11.681 0.042 1.938
50 C9P C C9P N N N 0 -3.748 4.398 0.01
51 O9P O O9P N N N 0 -3.799 4.827 1.144
52 CAP C CAP R N N 0 -2.576 4.74 -0.873
53 OAP O OAP N N N 0 -2.867 4.359 -2.219
54 CBP C CBP N N N 0 -1.335 3.988 -0.387
55 CCP C CCP N N N 0 -0.184 4.216 -1.368
56 CDP C CDP N N N 0 -0.936 4.502 0.997
57 CEP C CEP N N N 0 -1.645 2.492 -0.305
58 HB H HB N N N 0 -12.799 -2.569 -0.149
59 HBA H HBA N N N 0 -13.732 -1.12 -0.591
60 H1D H H1D N N N 0 6.763 -2.882 1.303
61 H2A H H2A N N N 0 7.5 -7.622 1.565
62 HO2A H HO2A N N N 0 5.349 4.049 0.896
63 H2D H H2D N N N 0 9.362 -2.419 -0.171
64 HO2D H HO2D N N N 0 9.194 -3.764 1.821
65 H2P H H2P N N N 0 -10.469 -1.075 -0.169
66 H2PA H H2PA N N N 0 -11.402 0.375 -0.611
67 H3B H H3B N N N 0 -16.765 -3.333 2.132
68 H3D H H3D N N N 0 9.266 -0.127 0.115
69 H3P H H3P N N N 0 -10.516 1.554 1.382
70 H3PA H H3PA N N N 0 -9.582 0.104 1.825
71 H4B H H4B N N N 0 -18.438 -4.75 1.019
72 H4D H H4D N N N 0 6.652 -0.255 1.631
73 HN4P H HN4P N N N 0 -8.913 0.818 -0.825
74 HO5A H HO5A N N N 0 1.913 1.888 -3.077
75 H5B H H5B N N N 0 -18.19 -5.318 -1.362
76 H5D H H5D N N N 0 7.556 1.816 0.472
77 H5DA H H5DA N N N 0 7.412 0.948 -1.075
78 HN6A H HN6A N N N 0 7.191 -8.677 -2.861
79 HN6B H HN6B N N N 0 7.084 -7.214 -3.681
80 H6B H H6B N N N 0 -16.269 -4.474 -2.645
81 H6P H H6P N N N 0 -6.293 1.441 -0.731
82 H6PA H H6PA N N N 0 -7.226 2.891 -1.174
83 H7B H H7B N N N 0 -14.586 -3.049 -1.557
84 H7P H H7P N N N 0 -6.34 4.07 0.82
85 H7PA H H7PA N N N 0 -5.407 2.62 1.262
86 H8A H H8A N N N 0 7.039 -2.535 -2.473
87 HO8A H HO8A N N N 0 11.156 1.593 4.286
88 HN8P H HN8P N N N 0 -4.738 3.334 -1.387
89 HO9A H HO9A N N N 0 11.89 -0.801 2.363
90 HAP H HAP N N N 0 -2.39 5.813 -0.831
91 HOAP H HOAP N N N 0 -3.044 3.415 -2.332
92 HDPA H HDPA N N N 0 -0.008 4.023 1.309
93 HCP H HCP N N N 0 0.037 5.282 -1.427
94 HCPA H HCPA N N N 0 -0.468 3.85 -2.355
95 HDP H HDP N N N 0 -1.724 4.269 1.713
96 HDPB H HDPB N N N 0 -0.79 5.582 0.955
97 HEP H HEP N N N 0 -1.93 2.125 -1.291
98 HEPA H HEPA N N N 0 -0.762 1.956 0.041
99 HEPB H HEPB N N N 0 -2.466 2.329 0.394



0FQ : Chemical Bonds

Total Number of Bonds: 102
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C1B CB C C sing 1.51 N N
2 CB S1P C S sing 1.81 N N
3 CB HB C H sing 1.09 N N
4 CB HBA C H sing 1.09 N N
5 C6A N1A C N doub 1.33 N Y
6 N1A C2A N C sing 1.32 N Y
7 P1A O1A P O doub 1.48 N N
8 O3A P1A O P sing 1.61 N N
9 O5D P1A O P sing 1.61 N N
10 P1A O2A P O sing 1.61 N N
11 C2B C1B C C sing 1.47 N N
12 C1B O1B C O doub 1.21 N N
13 N9A C1D N C sing 1.47 N N
14 C1D O4D C O sing 1.44 N N
15 C1D C2D C C sing 1.54 N N
16 C1D H1D C H sing 1.09 N N
17 S1P C2P S C sing 1.81 N N
18 C2A N3A C N doub 1.32 N Y
19 C2A H2A C H sing 1.08 N N
20 O2A HO2A O H sing 0.97 N N
21 O6A P2A O P sing 1.61 N N
22 O4A P2A O P doub 1.48 N N
23 O5A P2A O P sing 1.61 N N
24 P2A O3A P O sing 1.61 N N
25 C7B C2B C C doub 1.4 N Y
26 C3B C2B C C sing 1.4 N Y
27 C2D O2D C O sing 1.43 N N
28 C2D C3D C C sing 1.55 N N
29 C2D H2D C H sing 1.09 N N
30 O2D HO2D O H sing 0.97 N N
31 C2P C3P C C sing 1.53 N N
32 C2P H2P C H sing 1.09 N N
33 C2P H2PA C H sing 1.09 N N
34 C4A N3A C N sing 1.33 N Y
35 C4B C3B C C doub 1.38 N Y
36 C3B H3B C H sing 1.08 N N
37 C4D C3D C C sing 1.54 N N
38 C3D O3D C O sing 1.43 N N
39 C3D H3D C H sing 1.09 N N
40 O3D P3D O P sing 1.61 N N
41 O7A P3D O P doub 1.48 N N
42 P3D O9A P O sing 1.61 N N
43 P3D O8A P O sing 1.61 N N
44 C3P N4P C N sing 1.46 N N
45 C3P H3P C H sing 1.09 N N
46 C3P H3PA C H sing 1.09 N N
47 C5A C4A C C doub 1.4 N Y
48 C4A N9A C N sing 1.37 N Y
49 C5B C4B C C sing 1.38 N Y
50 C4B H4B C H sing 1.08 N N
51 O4D C4D O C sing 1.44 N N
52 C4D C5D C C sing 1.53 N N
53 C4D H4D C H sing 1.09 N N
54 N4P C5P N C sing 1.35 N N
55 N4P HN4P N H sing 0.97 N N
56 C6A C5A C C sing 1.41 N Y
57 C5A N7A C N sing 1.36 N Y
58 O5A HO5A O H sing 0.97 N N
59 C5B C6B C C doub 1.38 N Y
60 C5B H5B C H sing 1.08 N N
61 O5D C5D O C sing 1.43 N N
62 C5D H5D C H sing 1.09 N N
63 C5D H5DA C H sing 1.09 N N
64 C5P C6P C C sing 1.51 N N
65 C5P O5P C O doub 1.21 N N
66 N6A C6A N C sing 1.38 N N
67 N6A HN6A N H sing 0.97 N N
68 N6A HN6B N H sing 0.97 N N
69 CCP O6A C O sing 1.43 N N
70 C6B C7B C C sing 1.38 N Y
71 C6B H6B C H sing 1.08 N N
72 C6P C7P C C sing 1.53 N N
73 C6P H6P C H sing 1.09 N N
74 C6P H6PA C H sing 1.09 N N
75 N7A C8A N C doub 1.3 N Y
76 C7B H7B C H sing 1.08 N N
77 C7P N8P C N sing 1.47 N N
78 C7P H7P C H sing 1.09 N N
79 C7P H7PA C H sing 1.09 N N
80 C8A N9A C N sing 1.36 N Y
81 C8A H8A C H sing 1.08 N N
82 O8A HO8A O H sing 0.97 N N
83 N8P C9P N C sing 1.35 N N
84 N8P HN8P N H sing 0.97 N N
85 O9A HO9A O H sing 0.97 N N
86 O9P C9P O C doub 1.21 N N
87 C9P CAP C C sing 1.51 N N
88 CBP CAP C C sing 1.53 N N
89 CAP OAP C O sing 1.43 N N
90 CAP HAP C H sing 1.09 N N
91 OAP HOAP O H sing 0.97 N N
92 CEP CBP C C sing 1.53 N N
93 CDP CBP C C sing 1.53 N N
94 CBP CCP C C sing 1.53 N N
95 CCP HCP C H sing 1.09 N N
96 CCP HCPA C H sing 1.09 N N
97 CDP HDP C H sing 1.09 N N
98 CDP HDPA C H sing 1.09 N N
99 CDP HDPB C H sing 1.09 N N
100 CEP HEP C H sing 1.09 N N
101 CEP HEPA C H sing 1.09 N N
102 CEP HEPB C H sing 1.09 N N



0FQ : Used in PDB Entries

Total Number of PDB Entries: 3
Ligand Code PDB Entry ID Type Total Distinct
0FQ 4k4a Open in New Window Bound ligand 4 1
0FQ 4k4c Open in New Window Bound ligand 4 1
0FQ 4qd8 Open in New Window Bound ligand 4 1