3-(Naphth-1-yl)-2-thioxoimidazolidin-4-one

ID: ALA4210802

PubChem CID: 843351

Max Phase: Preclinical

Molecular Formula: C13H10N2OS

Molecular Weight: 242.30

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C1CNC(=S)N1c1cccc2ccccc12

Standard InChI:  InChI=1S/C13H10N2OS/c16-12-8-14-13(17)15(12)11-7-3-5-9-4-1-2-6-10(9)11/h1-7H,8H2,(H,14,17)

Standard InChI Key:  KGSGCXMWBVAYPH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
    2.6827   -9.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999   -9.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -8.3486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913   -7.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325   -8.3486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900   -7.0493    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9794   -9.7870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5280   -8.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0830   -7.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4716   -7.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970   -7.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9114   -8.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1341   -8.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9616   -9.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656   -9.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3447   -9.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5134   -8.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  2  0
  2  7  2  0
  8 13  2  0
 12  9  2  0
  9 10  1  0
 10 11  2  0
 11  8  1  0
  3  8  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
M  END

Alternative Forms

Associated Targets(Human)

PSMB2 Tclin Proteasome Macropain subunit (1025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PSMB1 Tclin Proteasome component C5 (935 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PSMB5 Tclin Proteasome Macropain subunit MB1 (2451 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: 242.30Molecular Weight (Monoisotopic): 242.0514AlogP: 2.06#Rotatable Bonds: 1
Polar Surface Area: 32.34Molecular Species: NEUTRALHBA: 2HBD: 1
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 11.38CX Basic pKa: CX LogP: 2.31CX LogD: 2.31
Aromatic Rings: 2Heavy Atoms: 17QED Weighted: 0.78Np Likeness Score: -0.87

References

1. Maccari R, Ettari R, Adornato I, Naß A, Wolber G, Bitto A, Mannino F, Aliquò F, Bruno G, Nicolò F, Previti S, Grasso S, Zappalà M, Ottanà R..  (2018)  Identification of 2-thioxoimidazolidin-4-one derivatives as novel noncovalent proteasome and immunoproteasome inhibitors.,  28  (3): [PMID:29292224] [10.1016/j.bmcl.2017.12.053]

Source