Chemical Components in the PDB

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EPR : Summary

Code

EPR

One-letter code

X

Molecule name

{5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid

Synonyms

Epalrestat

Systematic names

ProgramVersionName
ACDLabs 12.01 {(5E)-5-[(2E)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic acid
OpenEye OEToolkits 1.7.6 2-[5-[(E)-2-methyl-3-phenyl-prop-2-enylidene]-4-oxidanylidene-2-sulfanylidene-1,3-thiazolidin-3-yl]ethanoic acid

Formula

C15 H13 N O3 S2

Formal charge

0

Molecular weight

319.399 Da

SMILES

TypeProgramVersionDescriptor
SMILES ACDLabs 12.01 S=C1S/C(C(=O)N1CC(=O)O)=C/C(=C/c2ccccc2)C
SMILES CACTVS 3.370 CC(=Cc1ccccc1)C=C2SC(=S)N(CC(O)=O)C2=O
SMILES OpenEye OEToolkits 1.7.6 CC(=Cc1ccccc1)C=C2C(=O)N(C(=S)S2)CC(=O)O
Canonical SMILES CACTVS 3.370 CC(=C\c1ccccc1)/C=C2/SC(=S)N(CC(O)=O)C2=O
Canonical SMILES OpenEye OEToolkits 1.7.6 C/C(=C\c1ccccc1)/C=C2C(=O)N(C(=S)S2)CC(=O)O

IUPAC InChI

InChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8?

IUPAC InChI key

CHNUOJQWGUIOLD-KEBJEMEDSA-N
EPR

wwPDB Information

Atom count

34 (21 without Hydrogen)

Polymer type

Bound ligand

Type description

NON-POLYMER

Type code

HETAIN

Is modified

No

Standard parent

Not Assigned

Defined at

2013-03-25

Last modified at

2013-10-18

Status

Released

Obsoleted

Not Assigned



EPR : Atoms of Molecule

Total Number of Atoms: 34
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 1.774 1.558 0.699
2 C10 C C10 N N N 0 -0.595 1.592 0.299
3 C11 C C11 N N N 0 -0.752 0.178 -0.053
4 C12 C C12 N N N 0 -2.946 0.743 -0.438
5 C13 C C13 N N N 0 -2.26 -1.563 -0.789
6 C14 C C14 N N N 0 -2.671 -2.34 0.435
7 C15 C C15 N Y N 0 4.316 0.167 -1.522
8 C16 C C16 N Y N 0 3.447 0.171 -0.425
9 C17 C C17 N Y N 0 3.737 -0.623 0.691
10 C18 C C18 N Y N 0 4.878 -1.397 0.703
11 C19 C C19 N Y N 0 5.735 -1.391 -0.384
12 C20 C C20 N Y N 0 5.455 -0.608 -1.491
13 C8 C C8 N N N 0 2.233 0.999 -0.446
14 C9 C C9 N N N 0 0.538 2.234 0.706
15 C91 C C91 N N N 0 2.584 1.454 1.965
16 H10 H H10 N N N 0 5.103 -2.01 1.563
17 H11 H H11 N N N 0 6.627 -2.0 -0.368
18 H12 H H12 N N N 0 6.129 -0.608 -2.335
19 H13 H H13 N N N 0 -3.069 -1.582 -1.52
20 H131 H H131 N N N 0 4.096 0.773 -2.388
21 H13A H H13A N N N 0 -1.368 -2.013 -1.223
22 H5 H H5 N N N 0 1.707 1.163 -1.375
23 H6 H H6 N N N 0 2.331 0.53 2.484
24 H7 H H7 N N N 0 3.646 1.454 1.718
25 H8 H H8 N N N 0 2.362 2.305 2.609
26 H9 H H9 N N N 0 0.487 3.262 1.035
27 H91 H H91 N N N 0 3.07 -0.629 1.54
28 HO2 H HO2 N N N 0 -3.24 -4.098 1.143
29 N N N N N N 0 -1.974 -0.176 -0.414
30 O O O N N N 0 0.174 -0.613 -0.015
31 O1 O O1 N N N 0 -2.719 -1.792 1.511
32 O2 O O2 N N N 0 -2.983 -3.642 0.33
33 S S S N N N 0 -4.581 0.488 -0.876
34 S1 S S1 N N N 0 -2.217 2.276 0.073



EPR : Chemical Bonds

Total Number of Bonds: 35
Record First Atom Second Atom First Element Second Element Bond Order Type Bond Length Bond Stereochemistry Is Aromatic
1 N C13 N C sing 1.46 N N
2 C1 C9 C C sing 1.41 N N
3 O1 C14 O C doub 1.21 N N
4 S1 C10 S C sing 1.77 N N
5 S1 C12 S C sing 1.77 N N
6 C9 C10 C C doub 1.36 E N
7 C10 C11 C C sing 1.47 N N
8 C11 N C N sing 1.32 N N
9 C11 O C O doub 1.22 N N
10 C12 N C N sing 1.34 N N
11 C12 S C S doub 1.71 N N
12 C13 C14 C C sing 1.51 N N
13 C14 O2 C O sing 1.34 N N
14 C1 C8 C C doub 1.35 E N
15 C1 C91 C C sing 1.51 N N
16 C8 C16 C C sing 1.47 N N
17 C16 C17 C C doub 1.4 N Y
18 C16 C15 C C sing 1.4 N Y
19 C17 C18 C C sing 1.38 N Y
20 C18 C19 C C doub 1.38 N Y
21 C19 C20 C C sing 1.38 N Y
22 C20 C15 C C doub 1.38 N Y
23 O2 HO2 O H sing 0.97 N N
24 C9 H9 C H sing 1.08 N N
25 C13 H13 C H sing 1.09 N N
26 C13 H13A C H sing 1.09 N N
27 C8 H5 C H sing 1.08 N N
28 C91 H6 C H sing 1.09 N N
29 C91 H7 C H sing 1.09 N N
30 C91 H8 C H sing 1.09 N N
31 C17 H91 C H sing 1.08 N N
32 C18 H10 C H sing 1.08 N N
33 C19 H11 C H sing 1.08 N N
34 C20 H12 C H sing 1.08 N N
35 C15 H131 C H sing 1.08 N N



EPR : Used in PDB Entries

Total Number of PDB Entries: 2
Ligand Code PDB Entry ID Type Total Distinct
EPR 4jih Open in New Window Bound ligand 1 1
EPR 4jir Open in New Window Bound ligand 1 1