S-(N-Hydroxy-N-(4-chlorophenyl)carbamoyl)glutathione

ID: ALA1160350

PubChem CID: 392749

Max Phase: Preclinical

Molecular Formula: C17H21ClN4O8S

Molecular Weight: 476.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCC(=O)NC(CSC(=O)N(O)c1ccc(Cl)cc1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C17H21ClN4O8S/c18-9-1-3-10(4-2-9)22(30)17(29)31-8-12(15(26)20-7-14(24)25)21-13(23)6-5-11(19)16(27)28/h1-4,11-12,30H,5-8,19H2,(H,20,26)(H,21,23)(H,24,25)(H,27,28)

Standard InChI Key:  AJDQQFLYKZABLT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    5.2167   -3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -2.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -5.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -3.9750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -5.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -2.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -5.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -2.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -6.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -6.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0750   -5.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -6.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -4.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -5.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -1.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1042   -3.5875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  3  2  1  0
  4  1  1  0
  5  2  1  0
  6 16  1  0
  7  1  1  0
  8  5  1  0
  9  3  1  0
 10 22  1  0
 11  4  1  0
 12  7  1  0
 13 16  1  0
 14  1  2  0
 15  6  1  0
 16 25  1  0
 17  3  2  0
 18 10  1  0
 19  6  2  0
 20  8  2  0
 21 10  2  0
 22  9  1  0
 23 11  1  0
 24 11  2  0
 25 26  1  0
 26  8  1  0
 27  4  1  0
 28 29  2  0
 29 24  1  0
 30 23  2  0
 31 28  1  0
 30 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160350

   2-Amino-5-[[1-(carboxymethylamino)-3-[(4-chlorophenyl)-hydroxycarbamoyl]sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 476.90

Molecular Weight (Monoisotopic): 476.0769

AlogP: 0.27

#Rotatable Bonds: 11

Polar Surface Area: 199.36

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.72

CX Basic pKa: 9.35

CX LogP: -2.96

CX LogD: -6.29

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: -0.05

References

1. Murthy NS, Bakeris T, Kavarana MJ, Hamilton DS, Lan Y, Creighton DJ..  (1994)  S-(N-aryl-N-hydroxycarbamoyl)glutathione derivatives are tight-binding inhibitors of glyoxalase I and slow substrates for glyoxalase II.,  37  (14): [PMID:8035422] [10.1021/jm00040a007]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays