S-(N-4chlorophenyl-N-hydroxycarbamoyl)glutathione

ID: ALA131578

Chembl Id: CHEMBL131578

PubChem CID: 10322772

Max Phase: Preclinical

Molecular Formula: C17H21ClN4O8S

Molecular Weight: 476.90

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](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)/t11-,12-/m0/s1

Standard InChI Key:  AJDQQFLYKZABLT-RYUDHWBXSA-N

Alternative Forms

Associated Targets(Human)

GLO1 Tchem Glyoxalase I (402 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

HAGH Hydroxyacylglutathione hydrolase, mitochondrial (3 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 476.90Molecular Weight (Monoisotopic): 476.0769AlogP: 0.27#Rotatable Bonds: 11
Polar Surface Area: 199.36Molecular Species: ZWITTERIONHBA: 8HBD: 6
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 7#RO5 Violations (Lipinski): 2
CX Acidic pKa: 1.72CX Basic pKa: 9.35CX LogP: -2.96CX LogD: -6.29
Aromatic Rings: 1Heavy Atoms: 31QED Weighted: 0.19Np Likeness Score: -0.05

References

1. Kalsi A, Kavarana MJ, Lu T, Whalen DL, Hamilton DS, Creighton DJ..  (2000)  Role of hydrophobic interactions in binding S-(N-aryl/alkyl-N-hydroxycarbamoyl)glutathiones to the active site of the antitumor target enzyme glyoxalase I.,  43  (21): [PMID:11052803] [10.1021/jm000160l]
2. Holewinski RJ, Creighton DJ..  (2014)  Inhibition by active site directed covalent modification of human glyoxalase I.,  22  (13): [PMID:24856185] [10.1016/j.bmc.2014.04.055]
3. Sang Y, Shi Q, Mo M, Ni C, Li Z, Liu B, Deng Q, Creighton DJ, Zheng ZB..  (2015)  Novel bivalent inhibitors with sub-nanomolar affinities towards human glyoxalase I.,  25  (21): [PMID:26320622] [10.1016/j.bmcl.2015.08.055]
4. Jin T, Zhao L, Wang HP, Huang ML, Yue Y, Lu C, Zheng ZB..  (2020)  Recent advances in the discovery and development of glyoxalase I inhibitors.,  28  (4): [PMID:31879183] [10.1016/j.bmc.2019.115243]

Source