Chemical Components in the PDB

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478 : Summary

Code

478

One-letter code

X

Molecule name

{3-[(4-AMINO-BENZENESULFONYL)-ISOBUTYL-AMINO]-1-BENZYL-2-HYDROXY-PROPYL}-CARBAMIC ACID TETRAHYDRO-FURAN-3-YL ESTER

Synonyms

Amprenavir

Systematic names

ProgramVersionName
ACDLabs 12.01 (3S)-tetrahydrofuran-3-yl [(2S,3R)-4-{[(4-aminophenyl)sulfonyl](2-methylpropyl)amino}-3-hydroxy-1-phenylbutan-2-yl]carbamate
OpenEye OEToolkits 1.7.0 [(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate

Formula

C25 H35 N3 O6 S

Formal charge

0

Molecular weight

505.627 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=C(OC1CCOC1)NC(Cc2ccccc2)C(O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3
SMILES CACTVS 3.370 CC(C)CN(C[CH](O)[CH](Cc1ccccc1)NC(=O)O[CH]2CCOC2)[S](=O)(=O)c3ccc(N)cc3
SMILES OpenEye OEToolkits 1.7.0 CC(C)CN(CC(C(Cc1ccccc1)NC(=O)OC2CCOC2)O)S(=O)(=O)c3ccc(cc3)N
Canonical SMILES CACTVS 3.370 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]2CCOC2)[S](=O)(=O)c3ccc(N)cc3
Canonical SMILES OpenEye OEToolkits 1.7.0 CC(C)C[N@](C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)c3ccc(cc3)N

IUPAC InChI

InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1

IUPAC InChI key

YMARZQAQMVYCKC-OEMFJLHTSA-N
478

wwPDB Information

Atom count

70 (35 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

1999-07-08

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



478 : Atoms of Molecule

Total Number of Atoms: 70
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C1 C C1 N N N 0 6.097 0.699 -0.449
2 C2 C C2 N N N 0 5.942 0.687 -2.882
3 C3 C C3 N N N 0 3.027 -0.2 -0.841
4 C4 C C4 S N N 0 5.263 0.123 -1.61
5 C5 C C5 S N N 0 0.799 -0.681 0.02
6 C6 C C6 R N N 0 -0.624 -0.432 -0.484
7 C7 C C7 N N N 0 0.879 -0.344 1.51
8 C8 C C8 N Y N 0 2.245 -0.704 2.035
9 C9 C C9 N Y N 0 3.264 0.229 2.006
10 C10 C C10 N Y N 0 2.477 -1.966 2.55
11 C11 C C11 N Y N 0 4.517 -0.102 2.487
12 C12 C C12 N Y N 0 3.73 -2.296 3.031
13 C13 C C13 N Y N 0 4.751 -1.365 2.997
14 C14 C C14 N N N 0 -1.585 -1.404 0.203
15 C15 C C15 N N N 0 -3.243 -1.699 -1.695
16 C16 C C16 N N N 0 -3.619 -3.181 -1.644
17 C17 C C17 N Y N 0 -3.886 1.249 0.392
18 C18 C C18 N Y N 0 -4.494 1.919 -0.654
19 C19 C C19 N Y N 0 -4.329 3.283 -0.791
20 C20 C C20 N Y N 0 -3.552 3.982 0.124
21 C21 C C21 N Y N 0 -2.943 3.306 1.174
22 C22 C C22 N Y N 0 -3.112 1.941 1.304
23 C23 C C23 N N N 0 -4.914 -3.351 -0.848
24 C24 C C24 N N N 0 -3.822 -3.705 -3.067
25 C25 C C25 N N N 0 7.356 1.05 -2.361
26 N1 N N1 N N N 0 1.735 0.166 -0.723
27 N2 N N2 N N N 0 -2.933 -1.226 -0.344
28 N3 N N3 N N N 0 -3.383 5.362 -0.011
29 O1 O O1 N N N 0 3.888 0.579 -1.524
30 O2 O O2 N N N 0 3.415 -1.232 -0.331
31 O3 O O3 N N N 0 -1.008 0.911 -0.182
32 O4 O O4 N N N 0 -3.812 -0.798 1.922
33 O5 O O5 N N N 0 -5.346 -0.803 -0.051
34 O6 O O6 N N N 0 7.107 1.543 -1.027
35 S1 S S1 N N N 0 -4.105 -0.491 0.566
36 H11A H H11A N N N 0 5.457 1.285 0.211
37 H12A H H12A N N N 0 6.566 -0.112 0.108
38 H21A H H21A N N N 0 5.999 -0.072 -3.662
39 H22A H H22A N N N 0 5.42 1.574 -3.241
40 H4 H H4 N N N 0 5.306 -0.967 -1.606
41 H5 H H5 N N N 0 1.06 -1.729 -0.13
42 H6 H H6 N N N 0 -0.66 -0.587 -1.562
43 H71 H H71 N N N 0 0.705 0.723 1.651
44 H72 H H72 N N N 0 0.121 -0.91 2.052
45 H9 H H9 N N N 0 3.082 1.216 1.607
46 H10 H H10 N N N 0 1.679 -2.693 2.577
47 H11 H H11 N N N 0 5.314 0.627 2.464
48 H12 H H12 N N N 0 3.911 -3.282 3.434
49 H13 H H13 N N N 0 5.73 -1.624 3.373
50 H141 H H141 N N N 0 -1.254 -2.428 0.027
51 H142 H H142 N N N 0 -1.599 -1.206 1.275
52 H151 H H151 N N N 0 -2.371 -1.567 -2.336
53 H152 H H152 N N N 0 -4.079 -1.126 -2.097
54 H16 H H16 N N N 0 -2.819 -3.742 -1.16
55 H18 H H18 N N N 0 -5.097 1.375 -1.366
56 H19 H H19 N N N 0 -4.803 3.806 -1.608
57 H21 H H21 N N N 0 -2.338 3.846 1.887
58 H22 H H22 N N N 0 -2.639 1.415 2.12
59 H231 H H231 N N N 0 -5.714 -2.79 -1.331
60 H232 H H232 N N N 0 -5.182 -4.407 -0.811
61 H233 H H233 N N N 0 -4.77 -2.978 0.166
62 H241 H H241 N N N 0 -2.898 -3.584 -3.634
63 H242 H H242 N N N 0 -4.089 -4.761 -3.03
64 H243 H H243 N N N 0 -4.621 -3.145 -3.55
65 H251 H H251 N N N 0 7.993 0.166 -2.331
66 H252 H H252 N N N 0 7.805 1.827 -2.98
67 HN1 H HN1 N N N 0 1.426 0.99 -1.13
68 HN31 H HN31 N N N 0 -3.808 5.833 -0.744
69 HN32 H HN32 N N N 0 -2.84 5.849 0.629
70 HO3 H HO3 N N N 0 -0.933 1.14 0.754



478 : Chemical Bonds

Total Number of Bonds: 72
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 C1 C4 C C sing 1.54 N N
2 C1 O6 C O sing 1.44 N N
3 C1 H11A C H sing 1.09 N N
4 C1 H12A C H sing 1.09 N N
5 C2 C4 C C sing 1.55 N N
6 C2 C25 C C sing 1.55 N N
7 C2 H21A C H sing 1.09 N N
8 C2 H22A C H sing 1.09 N N
9 C3 N1 C N sing 1.35 N N
10 C3 O1 C O sing 1.35 N N
11 C3 O2 C O doub 1.21 N N
12 C4 O1 C O sing 1.45 N N
13 C4 H4 C H sing 1.09 N N
14 C5 C6 C C sing 1.53 N N
15 C5 C7 C C sing 1.53 N N
16 C5 N1 C N sing 1.46 N N
17 C5 H5 C H sing 1.09 N N
18 C6 C14 C C sing 1.53 N N
19 C6 O3 C O sing 1.43 N N
20 C6 H6 C H sing 1.09 N N
21 C7 C8 C C sing 1.51 N N
22 C7 H71 C H sing 1.09 N N
23 C7 H72 C H sing 1.09 N N
24 C8 C9 C C doub 1.38 N Y
25 C8 C10 C C sing 1.38 N Y
26 C9 C11 C C sing 1.38 N Y
27 C9 H9 C H sing 1.08 N N
28 C10 C12 C C doub 1.38 N Y
29 C10 H10 C H sing 1.08 N N
30 C11 C13 C C doub 1.38 N Y
31 C11 H11 C H sing 1.08 N N
32 C12 C13 C C sing 1.38 N Y
33 C12 H12 C H sing 1.08 N N
34 C13 H13 C H sing 1.08 N N
35 C14 N2 C N sing 1.47 N N
36 C14 H141 C H sing 1.09 N N
37 C14 H142 C H sing 1.09 N N
38 C15 C16 C C sing 1.53 N N
39 C15 N2 C N sing 1.46 N N
40 C15 H151 C H sing 1.09 N N
41 C15 H152 C H sing 1.09 N N
42 C16 C23 C C sing 1.53 N N
43 C16 C24 C C sing 1.53 N N
44 C16 H16 C H sing 1.09 N N
45 C17 C18 C C doub 1.38 N Y
46 C17 C22 C C sing 1.38 N Y
47 C17 S1 C S sing 1.76 N N
48 C18 C19 C C sing 1.38 N Y
49 C18 H18 C H sing 1.08 N N
50 C19 C20 C C doub 1.39 N Y
51 C19 H19 C H sing 1.08 N N
52 C20 C21 C C sing 1.39 N Y
53 C20 N3 C N sing 1.4 N N
54 C21 C22 C C doub 1.38 N Y
55 C21 H21 C H sing 1.08 N N
56 C22 H22 C H sing 1.08 N N
57 C23 H231 C H sing 1.09 N N
58 C23 H232 C H sing 1.09 N N
59 C23 H233 C H sing 1.09 N N
60 C24 H241 C H sing 1.09 N N
61 C24 H242 C H sing 1.09 N N
62 C24 H243 C H sing 1.09 N N
63 C25 O6 C O sing 1.44 N N
64 C25 H251 C H sing 1.09 N N
65 C25 H252 C H sing 1.09 N N
66 N1 HN1 N H sing 0.97 N N
67 N2 S1 N S sing 1.66 N N
68 N3 HN31 N H sing 0.97 N N
69 N3 HN32 N H sing 0.97 N N
70 O3 HO3 O H sing 0.97 N N
71 O4 S1 O S doub 1.42 N N
72 O5 S1 O S doub 1.42 N N



478 : Used in PDB Entries

Total Number of PDB Entries: 25
Ligand Code PDB Entry ID Type Total Distinct
478 1hpv Open in New Window Bound ligand 1 1
478 1t7j Open in New Window Bound ligand 1 1
478 3ekp Open in New Window Bound ligand 2 1
478 3ekv Open in New Window Bound ligand 1 1
478 3em3 Open in New Window Bound ligand 1 1
478 3nu3 Open in New Window Bound ligand 1 1
478 3nu4 Open in New Window Bound ligand 1 1
478 3nu5 Open in New Window Bound ligand 1 1
478 3nu6 Open in New Window Bound ligand 1 1
478 3nu9 Open in New Window Bound ligand 1 1
478 3nuj Open in New Window Bound ligand 1 1
478 3nuo Open in New Window Bound ligand 1 1
478 3oxv Open in New Window Bound ligand 3 1
478 3s43 Open in New Window Bound ligand 1 1
478 3s45 Open in New Window Bound ligand 1 1
478 3sm2 Open in New Window Bound ligand 1 1
478 4j5j Open in New Window Bound ligand 2 1
478 4jec Open in New Window Bound ligand 1 1
478 4rvj Open in New Window Bound ligand 2 1
478 5kr0 Open in New Window Bound ligand 1 1
478 5t8h Open in New Window Bound ligand 1 1
478 6p9b Open in New Window Bound ligand 1 1
478 6xct Open in New Window Bound ligand 1 1
478 7n6v Open in New Window Bound ligand 1 1
478 7n6x Open in New Window Bound ligand 1 1