2-Acetylamino-3-[3-(2-acetylamino-2-carboxy-ethylsulfanylcarbonylamino)-phenylcarbamoylsulfanyl]-propionic acid

ID: ALA190827

Chembl Id: CHEMBL190827

PubChem CID: 44398845

Max Phase: Preclinical

Molecular Formula: C18H22N4O8S2

Molecular Weight: 486.53

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(=O)NC(CSC(=O)Nc1cccc(NC(=O)SCC(NC(C)=O)C(=O)O)c1)C(=O)O

Standard InChI:  InChI=1S/C18H22N4O8S2/c1-9(23)19-13(15(25)26)7-31-17(29)21-11-4-3-5-12(6-11)22-18(30)32-8-14(16(27)28)20-10(2)24/h3-6,13-14H,7-8H2,1-2H3,(H,19,23)(H,20,24)(H,21,29)(H,22,30)(H,25,26)(H,27,28)

Standard InChI Key:  JSFCUSVJNDMUFQ-UHFFFAOYSA-N

Associated Targets(non-human)

GLR1 Glutathione reductase (23 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: 486.53Molecular Weight (Monoisotopic): 486.0879AlogP: 1.40#Rotatable Bonds: 10
Polar Surface Area: 191.00Molecular Species: ACIDHBA: 8HBD: 6
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 6#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.00CX Basic pKa: CX LogP: 0.10CX LogD: -6.75
Aromatic Rings: 1Heavy Atoms: 32QED Weighted: 0.28Np Likeness Score: -0.31

References

1. Seefeldt T, Dwivedi C, Peitz G, Herman J, Carlson L, Zhang Z, Guan X..  (2005)  2-Acetylamino-3-[4-(2-acetylamino-2-carboxyethylsulfanylcarbonylamino)- phenylcarbamoylsulfanyl]propionic acid and its derivatives as a novel class of glutathione reductase inhibitors.,  48  (16): [PMID:16078841] [10.1021/jm050030i]

Source