S-D-Lactoylglutathione

ID: ALA1160348

PubChem CID: 44308724

Max Phase: Preclinical

Molecular Formula: C8H13NO6S

Molecular Weight: 251.26

Molecule Type: Small molecule

Names and Identifiers

Synonyms: S-D-Lactoylglutathione | CHEMBL1160348

Canonical SMILES:  C[C@@H](O)C(=O)SCC(C(=O)O)C(N)C(=O)O

Standard InChI:  InChI=1S/C8H13NO6S/c1-3(10)8(15)16-2-4(6(11)12)5(9)7(13)14/h3-5,10H,2,9H2,1H3,(H,11,12)(H,13,14)/t3-,4?,5?/m1/s1

Standard InChI Key:  DWPTUFGRYYIXHG-JYMNUSQCSA-N

Molfile:  

     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
    4.5042   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -5.6250    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
    3.7917   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -3.1500    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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -5.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042   -6.8625    0.0000 O   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
    3.0750   -6.8625    0.0000 O   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
    5.9292   -2.7375    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
    6.5167   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -3.1500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  7  1  0
  6  1  1  0
  7  6  1  0
  8  2  1  0
  9  3  1  0
 10  4  1  0
 11  3  2  0
 12  4  2  0
 13  5  2  0
 14  5  1  0
 15 14  1  0
 14 16  1  6
 14 17  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1160348

   2-amino-3-[[(2R)-2-hydroxypropanoyl]sulfanylmethyl]butanedioic 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: 251.26

Molecular Weight (Monoisotopic): 251.0464

AlogP: -1.26

#Rotatable Bonds: 6

Polar Surface Area: 137.92

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.63

CX Basic pKa: 9.64

CX LogP: -3.40

CX LogD: -5.86

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.46

Np Likeness Score: 0.57

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]

Source

Source(1):

• Scientific Literature