Chemical Components in the PDB

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017 : Summary

Code

017

One-letter code

X

Molecule name

(3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE

Synonyms

Darunavir
TMC114
UIC-94017

Systematic names

ProgramVersionName
ACDLabs 12.01 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate
OpenEye OEToolkits 1.7.0 [(3R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate

Formula

C27 H37 N3 O7 S

Formal charge

0

Molecular weight

547.664 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=S(=O)(c1ccc(N)cc1)N(CC(C)C)CC(O)C(NC(=O)OC2COC3OCCC23)Cc4ccccc4
SMILES CACTVS 3.370 CC(C)CN(C[CH](O)[CH](Cc1ccccc1)NC(=O)O[CH]2CO[CH]3OCC[CH]23)[S](=O)(=O)c4ccc(N)cc4
SMILES OpenEye OEToolkits 1.7.0 CC(C)CN(CC(C(Cc1ccccc1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)c4ccc(cc4)N
Canonical SMILES CACTVS 3.370 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]2CO[C@H]3OCC[C@@H]23)[S](=O)(=O)c4ccc(N)cc4
Canonical SMILES OpenEye OEToolkits 1.7.0 CC(C)C[N@@](C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]2CO[C@@H]3[C@H]2CCO3)O)S(=O)(=O)c4ccc(cc4)N

IUPAC InChI

InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1

IUPAC InChI key

CJBJHOAVZSMMDJ-HEXNFIEUSA-N
017

wwPDB Information

Atom count

75 (38 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2004-01-27

Last modified at

2020-05-22

Status

Released

Obsoleted

Not Assigned



017 : Atoms of Molecule

Total Number of Atoms: 75
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 N1 N N1 N N N 0 -2.266 5.752 0.374
2 C2 C C2 N Y N 0 -2.761 4.491 0.036
3 C3 C C3 N Y N 0 -2.068 3.688 -0.861
4 C4 C C4 N Y N 0 -2.56 2.441 -1.192
5 C5 C C5 N Y N 0 -3.742 1.992 -0.632
6 C6 C C6 N Y N 0 -4.434 2.788 0.262
7 C7 C C7 N Y N 0 -3.945 4.034 0.601
8 S8 S S8 N N N 0 -4.367 0.4 -1.058
9 O9 O O9 N N N 0 -5.765 0.438 -0.809
10 O10 O O10 N N N 0 -3.812 0.077 -2.326
11 N11 N N11 N N N 0 -3.729 -0.682 0.021
12 C12 C C12 N N N 0 -4.439 -0.977 1.268
13 C13 C C13 N N N 0 -5.331 -2.205 1.069
14 C14 C C14 N N N 0 -4.457 -3.433 0.808
15 C15 C C15 N N N 0 -6.171 -2.434 2.327
16 C16 C C16 N N N 0 -2.456 -1.344 -0.271
17 C17 C C17 R N N 0 -1.312 -0.556 0.371
18 O18 O O18 N N N 0 -1.444 -0.6 1.793
19 C19 C C19 S N N 0 0.026 -1.175 -0.037
20 N20 N N20 N N N 0 1.123 -0.352 0.479
21 C21 C C21 N N N 0 2.325 -0.372 -0.13
22 O22 O O22 N N N 0 2.499 -1.073 -1.107
23 O23 O O23 N N N 0 3.332 0.384 0.345
24 C24 C C24 R N N 0 4.599 0.313 -0.361
25 C25 C C25 N N N 0 4.667 1.397 -1.452
26 O26 O O26 N N N 0 5.72 2.302 -1.092
27 C27 C C27 R N N 0 6.661 1.584 -0.271
28 O28 O O28 N N N 0 7.251 2.499 0.663
29 C29 C C29 N N N 0 6.457 2.582 1.851
30 C30 C C30 N N N 0 5.261 1.622 1.681
31 C31 C C31 S N N 0 5.766 0.642 0.593
32 C32 C C32 N N N 0 0.132 -2.588 0.542
33 C33 C C33 N Y N 0 2.571 -3.112 0.752
34 C34 C C34 N Y N 0 3.727 -3.713 0.292
35 C35 C C35 N Y N 0 3.706 -4.444 -0.881
36 C36 C C36 N Y N 0 2.529 -4.576 -1.593
37 C37 C C37 N Y N 0 1.372 -3.974 -1.132
38 C38 C C38 N Y N 0 1.393 -3.243 0.04
39 H11 H H11 N N N 0 -1.437 6.069 -0.018
40 H12 H H12 N N N 0 -2.753 6.314 0.998
41 H3 H H3 N N N 0 -1.145 4.039 -1.299
42 H4 H H4 N N N 0 -2.022 1.817 -1.89
43 H6 H H6 N N N 0 -5.357 2.434 0.697
44 H7 H H7 N N N 0 -4.484 4.654 1.303
45 H121 H H121 N N N 0 -3.716 -1.178 2.059
46 H122 H H122 N N N 0 -5.055 -0.122 1.547
47 H13 H H13 N N N 0 -5.991 -2.04 0.217
48 H141 H H141 N N N 0 -3.959 -3.326 -0.156
49 H142 H H142 N N N 0 -3.708 -3.52 1.595
50 H143 H H143 N N N 0 -5.081 -4.327 0.798
51 H151 H H151 N N N 0 -6.793 -1.559 2.513
52 H152 H H152 N N N 0 -6.806 -3.309 2.185
53 H153 H H153 N N N 0 -5.511 -2.599 3.179
54 H161 H H161 N N N 0 -2.471 -2.356 0.133
55 H162 H H162 N N N 0 -2.307 -1.386 -1.35
56 H17 H H17 N N N 0 -1.351 0.48 0.035
57 H18 H H18 N N N 0 -1.418 -1.493 2.163
58 H19 H H19 N N N 0 0.088 -1.223 -1.124
59 H20 H H20 N N N 0 0.983 0.207 1.26
60 H24 H H24 N N N 0 4.733 -0.676 -0.8
61 H251 H H251 N N N 0 4.886 0.939 -2.416
62 H252 H H252 N N N 0 3.719 1.933 -1.501
63 H27 H H27 N N N 0 7.406 1.049 -0.859
64 H291 H H291 N N N 0 7.051 2.283 2.714
65 H292 H H292 N N N 0 6.096 3.601 1.985
66 H301 H H301 N N N 0 5.054 1.093 2.612
67 H302 H H302 N N N 0 4.378 2.161 1.337
68 H31 H H31 N N N 0 6.282 -0.238 0.977
69 H321 H H321 N N N 0 0.16 -2.533 1.63
70 H322 H H322 N N N 0 -0.732 -3.174 0.229
71 H33 H H33 N N N 0 2.586 -2.544 1.671
72 H34 H H34 N N N 0 4.648 -3.61 0.848
73 H35 H H35 N N N 0 4.61 -4.913 -1.241
74 H36 H H36 N N N 0 2.513 -5.146 -2.509
75 H37 H H37 N N N 0 0.452 -4.077 -1.689



017 : Chemical Bonds

Total Number of Bonds: 78
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 N1 C2 N C sing 1.4 N N
2 N1 H11 N H sing 0.97 N N
3 N1 H12 N H sing 0.97 N N
4 C2 C3 C C doub 1.39 N Y
5 C2 C7 C C sing 1.39 N Y
6 C3 C4 C C sing 1.38 N Y
7 C3 H3 C H sing 1.08 N N
8 C4 C5 C C doub 1.38 N Y
9 C4 H4 C H sing 1.08 N N
10 C5 C6 C C sing 1.38 N Y
11 C5 S8 C S sing 1.76 N N
12 C6 C7 C C doub 1.38 N Y
13 C6 H6 C H sing 1.08 N N
14 C7 H7 C H sing 1.08 N N
15 S8 O9 S O doub 1.42 N N
16 S8 O10 S O doub 1.42 N N
17 S8 N11 S N sing 1.66 N N
18 N11 C12 N C sing 1.46 N N
19 N11 C16 N C sing 1.46 N N
20 C12 C13 C C sing 1.53 N N
21 C12 H121 C H sing 1.09 N N
22 C12 H122 C H sing 1.09 N N
23 C13 C14 C C sing 1.53 N N
24 C13 C15 C C sing 1.53 N N
25 C13 H13 C H sing 1.09 N N
26 C14 H141 C H sing 1.09 N N
27 C14 H142 C H sing 1.09 N N
28 C14 H143 C H sing 1.09 N N
29 C15 H151 C H sing 1.09 N N
30 C15 H152 C H sing 1.09 N N
31 C15 H153 C H sing 1.09 N N
32 C16 C17 C C sing 1.53 N N
33 C16 H161 C H sing 1.09 N N
34 C16 H162 C H sing 1.09 N N
35 C17 O18 C O sing 1.43 N N
36 C17 C19 C C sing 1.53 N N
37 C17 H17 C H sing 1.09 N N
38 O18 H18 O H sing 0.97 N N
39 C19 N20 C N sing 1.47 N N
40 C19 C32 C C sing 1.53 N N
41 C19 H19 C H sing 1.09 N N
42 N20 C21 N C sing 1.35 N N
43 N20 H20 N H sing 0.97 N N
44 C21 O22 C O doub 1.21 N N
45 C21 O23 C O sing 1.35 N N
46 O23 C24 O C sing 1.45 N N
47 C24 C25 C C sing 1.54 N N
48 C24 C31 C C sing 1.54 N N
49 C24 H24 C H sing 1.09 N N
50 C25 O26 C O sing 1.43 N N
51 C25 H251 C H sing 1.09 N N
52 C25 H252 C H sing 1.09 N N
53 O26 C27 O C sing 1.44 N N
54 C27 O28 C O sing 1.43 N N
55 C27 C31 C C sing 1.56 N N
56 C27 H27 C H sing 1.09 N N
57 O28 C29 O C sing 1.43 N N
58 C29 C30 C C sing 1.54 N N
59 C29 H291 C H sing 1.09 N N
60 C29 H292 C H sing 1.09 N N
61 C30 C31 C C sing 1.55 N N
62 C30 H301 C H sing 1.09 N N
63 C30 H302 C H sing 1.09 N N
64 C31 H31 C H sing 1.09 N N
65 C32 C38 C C sing 1.51 N N
66 C32 H321 C H sing 1.09 N N
67 C32 H322 C H sing 1.09 N N
68 C33 C34 C C doub 1.38 N Y
69 C33 C38 C C sing 1.38 N Y
70 C33 H33 C H sing 1.08 N N
71 C34 C35 C C sing 1.38 N Y
72 C34 H34 C H sing 1.08 N N
73 C35 C36 C C doub 1.38 N Y
74 C35 H35 C H sing 1.08 N N
75 C36 C37 C C sing 1.38 N Y
76 C36 H36 C H sing 1.08 N N
77 C37 C38 C C doub 1.38 N Y
78 C37 H37 C H sing 1.08 N N



017 : Used in PDB Entries

Total Number of PDB Entries: 76
Ligand Code PDB Entry ID Type Total Distinct
017 1t3r Open in New Window Bound ligand 1 1
017 1t7i Open in New Window Bound ligand 1 1
017 2f80 Open in New Window Bound ligand 1 1
017 2f81 Open in New Window Bound ligand 1 1
017 2f8g Open in New Window Bound ligand 1 1
017 2hs1 Open in New Window Bound ligand 2 1
017 2hs2 Open in New Window Bound ligand 2 1
017 2idw Open in New Window Bound ligand 1 1
017 2ien Open in New Window Bound ligand 1 1
017 2ieo Open in New Window Bound ligand 1 1
017 3bvb Open in New Window Bound ligand 1 1
017 3cyw Open in New Window Bound ligand 1 1
017 3d1z Open in New Window Bound ligand 1 1
017 3d20 Open in New Window Bound ligand 1 1
017 3ebz Open in New Window Bound ligand 1 1
017 3ekt Open in New Window Bound ligand 2 1
017 3em6 Open in New Window Bound ligand 1 1
017 3ggu Open in New Window Bound ligand 1 1
017 3jvy Open in New Window Bound ligand 1 1
017 3jw2 Open in New Window Bound ligand 1 1
017 3lzs Open in New Window Bound ligand 1 1
017 3lzu Open in New Window Bound ligand 1 1
017 3lzv Open in New Window Bound ligand 1 1
017 3mws Open in New Window Bound ligand 1 1
017 3ogp Open in New Window Bound ligand 2 1
017 3oxw Open in New Window Bound ligand 2 1
017 3oy4 Open in New Window Bound ligand 1 1
017 3pwm Open in New Window Bound ligand 1 1
017 3s53 Open in New Window Bound ligand 2 1
017 3s54 Open in New Window Bound ligand 1 1
017 3so9 Open in New Window Bound ligand 1 1
017 3t3c Open in New Window Bound ligand 1 1
017 3tkw Open in New Window Bound ligand 1 1
017 3ttp Open in New Window Bound ligand 1 1
017 3u7s Open in New Window Bound ligand 2 1
017 3ucb Open in New Window Bound ligand 2 1
017 4dqb Open in New Window Bound ligand 1 1
017 4dqc Open in New Window Bound ligand 1 1
017 4dqe Open in New Window Bound ligand 1 1
017 4dqf Open in New Window Bound ligand 1 1
017 4dqh Open in New Window Bound ligand 1 1
017 4hla Open in New Window Bound ligand 1 1
017 4ll3 Open in New Window Bound ligand 2 1
017 4njt Open in New Window Bound ligand 2 1
017 4npt Open in New Window Bound ligand 1 1
017 4q1w Open in New Window Bound ligand 1 1
017 4q1x Open in New Window Bound ligand 1 1
017 4q1y Open in New Window Bound ligand 1 1
017 4yoa Open in New Window Bound ligand 1 1
017 5e5j Open in New Window Bound ligand 1 1
017 5e5k Open in New Window Bound ligand 1 1
017 5kqy Open in New Window Bound ligand 1 1
017 5kr1 Open in New Window Bound ligand 1 1
017 5t2z Open in New Window Bound ligand 1 1
017 6dgx Open in New Window Bound ligand 1 1
017 6dh0 Open in New Window Bound ligand 1 1
017 6dh3 Open in New Window Bound ligand 1 1
017 6dh6 Open in New Window Bound ligand 1 1
017 6oos Open in New Window Bound ligand 2 1
017 6oot Open in New Window Bound ligand 1 1
017 6oou Open in New Window Bound ligand 1 1
017 6ops Open in New Window Bound ligand 1 1
017 6opt Open in New Window Bound ligand 1 1
017 6opu Open in New Window Bound ligand 1 1
017 6opv Open in New Window Bound ligand 1 1
017 6opw Open in New Window Bound ligand 1 1
017 6opx Open in New Window Bound ligand 1 1
017 6opy Open in New Window Bound ligand 1 1
017 6opz Open in New Window Bound ligand 1 1
017 6p9a Open in New Window Bound ligand 1 1
017 6w6q Open in New Window Bound ligand 1 1
017 6xd2 Open in New Window Bound ligand 1 1
017 7map Open in New Window Bound ligand 1 1
017 7maq Open in New Window Bound ligand 1 1
017 7mar Open in New Window Bound ligand 2 1
017 7mas Open in New Window Bound ligand 2 1