Chemical Components in the PDB

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1R4 : Summary

Code

1R4

One-letter code

X

Molecule name

L-gamma-glutamyl-S-[2-(4-nitrophenyl)-2-oxoethyl]-L-cysteinylglycine

Synonyms

S-(4-nitrophenacyl)glutathione

Systematic names

ProgramVersionName
ACDLabs 12.01 L-gamma-glutamyl-S-[2-(4-nitrophenyl)-2-oxoethyl]-L-cysteinylglycine
OpenEye OEToolkits 1.7.6 (2S)-2-azanyl-5-[[(2R)-1-(2-hydroxy-2-oxoethylamino)-3-[2-(4-nitrophenyl)-2-oxidanylidene-ethyl]sulfanyl-1-oxidanylidene-propan-2-yl]amino]-5-oxidanylidene-pentanoic acid

Formula

C18 H22 N4 O9 S

Formal charge

0

Molecular weight

470.454 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 O=[N+]([O-])c1ccc(C(=O)CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)cc1
SMILES CACTVS 3.370 N[CH](CCC(=O)N[CH](CSCC(=O)c1ccc(cc1)[N+]([O-])=O)C(=O)NCC(O)=O)C(O)=O
SMILES OpenEye OEToolkits 1.7.6 c1cc(ccc1C(=O)CSCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N)[N+](=O)[O-]
Canonical SMILES CACTVS 3.370 N[C@@H](CCC(=O)N[C@@H](CSCC(=O)c1ccc(cc1)[N+]([O-])=O)C(=O)NCC(O)=O)C(O)=O
Canonical SMILES OpenEye OEToolkits 1.7.6 c1cc(ccc1C(=O)CSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)[N+](=O)[O-]

IUPAC InChI

InChI=1S/C18H22N4O9S/c19-12(18(28)29)5-6-15(24)21-13(17(27)20-7-16(25)26)8-32-9-14(23)10-1-3-11(4-2-10)22(30)31/h1-4,12-13H,5-9,19H2,(H,20,27)(H,21,24)(H,25,26)(H,28,29)/t12-,13-/m0/s1

IUPAC InChI key

DFOFAMKKGYFIOO-STQMWFEESA-N
1R4

wwPDB Information

Atom count

54 (32 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2013-01-22

Last modified at

2013-04-19

Status

Released

Obsoleted

Not Assigned



1R4 : Atoms of Molecule

Total Number of Atoms: 54
Record Atom Name Symbol PDB Name Stereochemistry Is Aromatic Is Leaving Atom Charge X-Coordinate Y-Coordinate Z-Coordinate
1 C02 C C02 N N N 0 -2.359 -2.47 0.343
2 C03 C C03 R N N 0 -1.67 -1.235 -0.178
3 C05 C C05 N N N 0 -3.349 0.523 -0.015
4 C06 C C06 N N N 0 -3.927 1.742 0.657
5 C07 C C07 N N N 0 -5.184 2.19 -0.093
6 C08 C C08 S N N 0 -5.771 3.427 0.59
7 C09 C C09 N N N 0 -6.935 3.941 -0.218
8 C14 C C14 N N N 0 -0.173 -1.321 0.123
9 C16 C C16 N N N 0 2.392 -0.118 -0.06
10 C17 C C17 N N N 0 3.226 1.05 -0.522
11 C18 C C18 N Y N 0 4.677 1.06 -0.278
12 C19 C C19 N Y N 0 5.454 2.142 -0.705
13 C20 C C20 N Y N 0 6.813 2.144 -0.473
14 C21 C C21 N Y N 0 7.409 1.079 0.18
15 C25 C C25 N Y N 0 6.647 0.0050 0.606
16 C26 C C26 N Y N 0 5.286 -0.01 0.386
17 C29 C C29 N N N 0 -2.665 -4.887 0.396
18 C30 C C30 N N N 0 -2.083 -6.106 -0.271
19 H01 H H01 N N N 0 -6.562 3.885 2.434
20 H011 H H011 N N N 0 -6.939 2.355 1.903
21 H031 H H031 N N N 0 -1.821 -1.162 -1.255
22 H041 H H041 N N N 0 -1.801 0.322 1.26
23 H061 H H061 N N N 0 -3.192 2.546 0.646
24 H062 H H062 N N N 0 -4.186 1.5 1.688
25 H071 H H071 N N N 0 -5.919 1.385 -0.081
26 H072 H H072 N N N 0 -4.925 2.431 -1.123
27 H081 H H081 N N N 0 -5.006 4.201 0.658
28 H1 H H1 N N N 0 -7.495 4.995 -1.796
29 H141 H H141 N N N 0 -0.022 -1.394 1.2
30 H142 H H142 N N N 0 0.245 -2.203 -0.363
31 H161 H H161 N N N 0 2.479 -0.221 1.021
32 H162 H H162 N N N 0 2.747 -1.03 -0.542
33 H191 H H191 N N N 0 4.991 2.973 -1.215
34 H2 H H2 N N N 0 -2.139 -8.079 -0.411
35 H201 H H201 N N N 0 7.415 2.978 -0.802
36 H251 H H251 N N N 0 7.119 -0.822 1.115
37 H261 H H261 N N N 0 4.693 -0.849 0.719
38 H281 H H281 N N N 0 -1.301 -3.766 -0.782
39 H291 H H291 N N N 0 -3.733 -4.83 0.182
40 H292 H H292 N N N 0 -2.514 -4.956 1.474
41 N01 N N01 N N N 0 -6.229 3.071 1.939
42 N04 N N04 N N N 0 -2.232 -0.05 0.475
43 N22 N N22 N N N 1 8.869 1.089 0.425
44 N28 N N28 N N N 0 -2.0 -3.686 -0.115
45 O01 O O01 N N N 0 -3.233 -2.37 1.178
46 O10 O O10 N N N 0 -8.066 3.68 0.12
47 O11 O O11 N N N 0 -6.717 4.688 -1.311
48 O13 O O13 N N N 0 -3.889 0.058 -0.996
49 O23 O O23 N N N -1 9.396 0.153 0.999
50 O24 O O24 N N N 0 9.542 2.033 0.052
51 O27 O O27 N N N 0 2.701 1.981 -1.094
52 O31 O O31 N N N 0 -2.543 -7.327 0.043
53 O32 O O32 N N N 0 -1.203 -5.984 -1.09
54 S15 S S15 N N N 0 0.657 0.165 -0.504



1R4 : Chemical Bonds

Total Number of Bonds: 54
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 N01 C08 N C sing 1.47 N N
2 C08 C09 C C sing 1.51 N N
3 C08 C07 C C sing 1.53 N N
4 S15 C16 S C sing 1.81 N N
5 S15 C14 S C sing 1.81 N N
6 C06 C07 C C sing 1.53 N N
7 C06 C05 C C sing 1.51 N N
8 O27 C17 O C doub 1.21 N N
9 O10 C09 O C doub 1.21 N N
10 N04 C05 N C sing 1.35 N N
11 N04 C03 N C sing 1.47 N N
12 C09 O11 C O sing 1.34 N N
13 C05 O13 C O doub 1.21 N N
14 C17 C16 C C sing 1.51 N N
15 C17 C18 C C sing 1.47 N N
16 C26 C25 C C doub 1.38 N Y
17 C26 C18 C C sing 1.4 N Y
18 C14 C03 C C sing 1.53 N N
19 O32 C30 O C doub 1.21 N N
20 C25 C21 C C sing 1.38 N Y
21 C18 C19 C C doub 1.4 N Y
22 C03 C02 C C sing 1.51 N N
23 N28 C02 N C sing 1.35 N N
24 N28 C29 N C sing 1.46 N N
25 C30 O31 C O sing 1.34 N N
26 C30 C29 C C sing 1.51 N N
27 C02 O01 C O doub 1.21 N N
28 O23 N22 O N sing 1.22 N N
29 C19 C20 C C sing 1.38 N Y
30 C21 N22 C N sing 1.48 N N
31 C21 C20 C C doub 1.38 N Y
32 N22 O24 N O doub 1.22 N N
33 C03 H031 C H sing 1.09 N N
34 N04 H041 N H sing 0.97 N N
35 C06 H062 C H sing 1.09 N N
36 C06 H061 C H sing 1.09 N N
37 C07 H072 C H sing 1.09 N N
38 C07 H071 C H sing 1.09 N N
39 C08 H081 C H sing 1.09 N N
40 O11 H1 O H sing 0.97 N N
41 C14 H141 C H sing 1.09 N N
42 C14 H142 C H sing 1.09 N N
43 C16 H161 C H sing 1.09 N N
44 C16 H162 C H sing 1.09 N N
45 C19 H191 C H sing 1.08 N N
46 C20 H201 C H sing 1.08 N N
47 C25 H251 C H sing 1.08 N N
48 C26 H261 C H sing 1.08 N N
49 N28 H281 N H sing 0.97 N N
50 C29 H292 C H sing 1.09 N N
51 C29 H291 C H sing 1.09 N N
52 O31 H2 O H sing 0.97 N N
53 N01 H01 N H sing 1.01 N N
54 N01 H011 N H sing 1.01 N N



1R4 : Used in PDB Entries

Total Number of PDB Entries: 1
Ligand Code PDB Entry ID Type Total Distinct
1R4 4is0 Open in New Window Bound ligand 1 1