S-(N-phenyl-N-hydroxycarbamoyl)glutathione

ID: ALA128935

Chembl Id: CHEMBL128935

PubChem CID: 10411076

Max Phase: Preclinical

Molecular Formula: C17H22N4O8S

Molecular Weight: 442.45

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)N[C@@H](CSC(=O)N(O)c1ccccc1)C(=O)NCC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C17H22N4O8S/c18-11(16(26)27)6-7-13(22)20-12(15(25)19-8-14(23)24)9-30-17(28)21(29)10-4-2-1-3-5-10/h1-5,11-12,29H,6-9,18H2,(H,19,25)(H,20,22)(H,23,24)(H,26,27)/t11-,12-/m0/s1

Standard InChI Key:  GAALWJSKDIUONK-RYUDHWBXSA-N

Alternative Forms

Associated Targets(Human)

GLO1 Tchem Glyoxalase I (402 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: 442.45Molecular Weight (Monoisotopic): 442.1158AlogP: -0.39#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: 9.37CX LogP: -3.56CX LogD: -6.88
Aromatic Rings: 1Heavy Atoms: 30QED Weighted: 0.19Np Likeness Score: 0.11

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. Perez C, Barkley-Levenson AM, Dick BL, Glatt PF, Martinez Y, Siegel D, Momper JD, Palmer AA, Cohen SM..  (2019)  Metal-Binding Pharmacophore Library Yields the Discovery of a Glyoxalase 1 Inhibitor.,  62  (3): [PMID:30628789] [10.1021/acs.jmedchem.8b01868]
3. 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