2-Acetylamino-3-[4-(2-acetylamino-2-carboxy-ethylsulfanylcarbonylamino)-butylcarbamoylsulfanyl]-propionic acid

ID: ALA191549

Chembl Id: CHEMBL191549

PubChem CID: 44398879

Max Phase: Preclinical

Molecular Formula: C16H26N4O8S2

Molecular Weight: 466.54

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H26N4O8S2/c1-9(21)19-11(13(23)24)7-29-15(27)17-5-3-4-6-18-16(28)30-8-12(14(25)26)20-10(2)22/h11-12H,3-8H2,1-2H3,(H,17,27)(H,18,28)(H,19,21)(H,20,22)(H,23,24)(H,25,26)

Standard InChI Key:  WGHZTKSSESOAMV-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: 466.54Molecular Weight (Monoisotopic): 466.1192AlogP: -0.17#Rotatable Bonds: 13
Polar Surface Area: 191.00Molecular Species: ACIDHBA: 8HBD: 6
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 6#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.33CX Basic pKa: CX LogP: -1.56CX LogD: -8.22
Aromatic Rings: Heavy Atoms: 30QED Weighted: 0.20Np Likeness Score: -0.01

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