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

ID: ALA1160349

Cas Number: 156727-62-7

PubChem CID: 375165

Max Phase: Preclinical

Molecular Formula: C17H21BrN4O8S

Molecular Weight: 521.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21BrN4O8S/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:  IQPLOQWSCZRUCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -5.4392    1.7831    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1524    0.1331    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5813   -0.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    1.3706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -0.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -3.1669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200   -1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    0.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634   -0.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5813    0.1331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910    0.5456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -1.1044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489    1.3706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958    0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2766    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2766   -0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0103    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2958    1.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379    0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    1.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0103    1.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4200    0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1345    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489    0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7055   -2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634    0.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0
  2 16  1  0
  2 21  1  0
  3 11  1  0
  4 16  2  0
  5 18  2  0
  6 25  2  0
  7 30  2  0
  8 30  1  0
  9 31  2  0
 10 31  1  0
 11 15  1  0
 11 16  1  0
 12 17  1  0
 12 25  1  0
 13 18  1  0
 13 27  1  0
 14 29  1  0
 15 19  2  0
 15 20  1  0
 17 18  1  0
 17 21  1  0
 19 23  1  0
 20 24  2  0
 22 23  2  0
 22 24  1  0
 25 26  1  0
 26 28  1  0
 27 30  1  0
 28 29  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160349

   (S)-2-amino-5-(((R)-3-(((4-bromophenyl)(hydroxy)carbamoyl)thio)-1-((carboxymethyl)amino)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid

2. Alternative Forms:

   

   ALA1160349

   Acetic acid;2-amino-5-[[3-[(4-bromophenyl)-hydroxycarbamoyl]sulfanyl-1-(carboxymethylamino)-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: 521.35

Molecular Weight (Monoisotopic): 520.0263

AlogP: 0.38

#Rotatable Bonds: 11

Polar Surface Area: 199.36

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.72

CX Basic pKa: 9.36

CX LogP: -2.80

CX LogD: -6.12

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: 0.04

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