Chemical Components in the PDB

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SH4 : Summary

Code

SH4

One-letter code

X

Molecule name

(1R)-1-PHENYLETHYL 4-(ACETYLAMINO)BENZYLPHOSPHONATE

Systematic names

ProgramVersionName
ACDLabs 10.04 (1S)-1-phenylethyl [4-(acetylamino)benzyl]phosphonate
OpenEye OEToolkits 1.5.0 (4-acetamidophenyl)methyl-[(1S)-1-phenylethoxy]phosphinate

Formula

C17 H19 N O4 P

Formal charge

-1

Molecular weight

332.311 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 10.04 O=C(Nc1ccc(cc1)CP([O-])(=O)OC(c2ccccc2)C)C
SMILES CACTVS 3.385 C[CH](O[P]([O-])(=O)Cc1ccc(NC(C)=O)cc1)c2ccccc2
SMILES OpenEye OEToolkits 1.7.5 CC(c1ccccc1)OP(=O)(Cc2ccc(cc2)NC(=O)C)[O-]
Canonical SMILES CACTVS 3.385 C[C@H](O[P]([O-])(=O)Cc1ccc(NC(C)=O)cc1)c2ccccc2
Canonical SMILES OpenEye OEToolkits 1.7.5 C[C@@H](c1ccccc1)OP(=O)(Cc2ccc(cc2)NC(=O)C)[O-]

IUPAC InChI

InChI=1S/C17H20NO4P/c1-13(16-6-4-3-5-7-16)22-23(20,21)12-15-8-10-17(11-9-15)18-14(2)19/h3-11,13H,12H2,1-2H3,(H,18,19)(H,20,21)/p-1/t13-/m0/s1

IUPAC InChI key

YPTMOJMDCPUCJT-ZDUSSCGKSA-M
SH4

wwPDB Information

Atom count

42 (23 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2003-09-29

Last modified at

2020-06-17

Status

Released

Obsoleted

Not Assigned



SH4 : Atoms of Molecule

Total Number of Atoms: 42
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 O1 O O1 N N N -1 -0.533 -2.246 -0.762
2 P1 P P1 N N N 0 -0.867 -0.909 -0.063
3 O2 O O2 N N N 0 -0.696 0.253 -1.067
4 O3 O O3 N N N 0 -2.388 -0.943 0.463
5 C1 C C1 S N N 0 -3.514 -1.018 -0.414
6 C2 C C2 N Y N 0 -4.391 0.19 -0.209
7 C3 C C3 N Y N 0 -5.058 0.749 -1.283
8 C4 C C4 N Y N 0 -5.862 1.858 -1.096
9 C5 C C5 N Y N 0 -6.0 2.407 0.165
10 C6 C C6 N Y N 0 -5.334 1.846 1.239
11 C7 C C7 N Y N 0 -4.533 0.735 1.053
12 C8 C C8 N N N 0 -4.314 -2.286 -0.109
13 C9 C C9 N N N 0 0.26 -0.663 1.349
14 C10 C C10 N Y N 0 1.671 -0.508 0.844
15 C11 C C11 N Y N 0 2.158 0.749 0.533
16 C12 C C12 N Y N 0 3.452 0.894 0.071
17 C13 C C13 N Y N 0 4.263 -0.222 -0.082
18 N1 N N1 N N N 0 5.574 -0.078 -0.549
19 C14 C C14 N N N 0 6.283 1.024 -0.237
20 O4 O O4 N N N 0 5.822 1.846 0.526
21 C15 C C15 N N N 0 7.649 1.236 -0.837
22 C16 C C16 N Y N 0 3.77 -1.483 0.231
23 C17 C C17 N Y N 0 2.478 -1.621 0.698
24 H1 H H1 N N N 0 -3.168 -1.046 -1.447
25 H3 H H3 N N N 0 -4.95 0.321 -2.269
26 H4 H H4 N N N 0 -6.383 2.296 -1.935
27 H5 H H5 N N N 0 -6.628 3.273 0.312
28 H6 H H6 N N N 0 -5.442 2.275 2.225
29 H7 H H7 N N N 0 -4.016 0.296 1.893
30 H81 H 1H8 N N N 0 -5.173 -2.344 -0.778
31 H82 H 2H8 N N N 0 -3.679 -3.161 -0.257
32 H83 H 3H8 N N N 0 -4.659 -2.259 0.924
33 H91 H 1H9 N N N 0 -0.032 0.235 1.894
34 H92 H 2H9 N N N 0 0.204 -1.526 2.012
35 H11 H H11 N N N 0 1.527 1.617 0.652
36 H12 H H12 N N N 0 3.832 1.876 -0.172
37 HN1 H HN1 N N N 0 5.972 -0.772 -1.098
38 H151 H 1H15 N N N 0 7.892 0.4 -1.492
39 H152 H 2H15 N N N 0 7.654 2.162 -1.412
40 H153 H 3H15 N N N 0 8.39 1.3 -0.039
41 H16 H H16 N N N 0 4.399 -2.353 0.113
42 H17 H H17 N N N 0 2.096 -2.601 0.945



SH4 : Chemical Bonds

Total Number of Bonds: 43
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 O1 P1 O P sing 1.55 N N
2 P1 O2 P O doub 1.55 N N
3 P1 O3 P O sing 1.61 N N
4 P1 C9 P C sing 1.82 N N
5 O3 C1 O C sing 1.43 N N
6 C1 C2 C C sing 1.51 N N
7 C1 C8 C C sing 1.53 N N
8 C1 H1 C H sing 1.09 N N
9 C2 C3 C C doub 1.38 N Y
10 C2 C7 C C sing 1.38 N Y
11 C3 C4 C C sing 1.38 N Y
12 C3 H3 C H sing 1.08 N N
13 C4 C5 C C doub 1.38 N Y
14 C4 H4 C H sing 1.08 N N
15 C5 C6 C C sing 1.38 N Y
16 C5 H5 C H sing 1.08 N N
17 C6 C7 C C doub 1.38 N Y
18 C6 H6 C H sing 1.08 N N
19 C7 H7 C H sing 1.08 N N
20 C8 H81 C H sing 1.09 N N
21 C8 H82 C H sing 1.09 N N
22 C8 H83 C H sing 1.09 N N
23 C9 C10 C C sing 1.51 N N
24 C9 H91 C H sing 1.09 N N
25 C9 H92 C H sing 1.09 N N
26 C10 C11 C C doub 1.38 N Y
27 C10 C17 C C sing 1.38 N Y
28 C11 C12 C C sing 1.38 N Y
29 C11 H11 C H sing 1.08 N N
30 C12 C13 C C doub 1.39 N Y
31 C12 H12 C H sing 1.08 N N
32 C13 N1 C N sing 1.4 N N
33 C13 C16 C C sing 1.39 N Y
34 N1 C14 N C sing 1.35 N N
35 N1 HN1 N H sing 0.97 N N
36 C14 O4 C O doub 1.21 N N
37 C14 C15 C C sing 1.51 N N
38 C15 H151 C H sing 1.09 N N
39 C15 H152 C H sing 1.09 N N
40 C15 H153 C H sing 1.09 N N
41 C16 C17 C C doub 1.38 N Y
42 C16 H16 C H sing 1.08 N N
43 C17 H17 C H sing 1.08 N N



SH4 : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
SH4 1um4 Open in New Window Bound ligand 1 1