5-Chloro-N-[[(4R)-2,5-dioxo-4-thiazol-2-yl-imidazolidin-4-yl]methyl]benzofuran-2-carboxamide

ID: ALA3358155

Chembl Id: CHEMBL3358155

PubChem CID: 86287515

Max Phase: Preclinical

Molecular Formula: C16H11ClN4O4S

Molecular Weight: 390.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)[C@](CNC(=O)c2cc3cc(Cl)ccc3o2)(c2nccs2)N1

Standard InChI:  InChI=1S/C16H11ClN4O4S/c17-9-1-2-10-8(5-9)6-11(25-10)12(22)19-7-16(14-18-3-4-26-14)13(23)20-15(24)21-16/h1-6H,7H2,(H,19,22)(H2,20,21,23,24)/t16-/m1/s1

Standard InChI Key:  LBVBVIKJOWWVJX-MRXNPFEDSA-N

Alternative Forms

1. Parent:

   

   ALA3358155

   5-Chloro-N-{[(4r)-2,5-Dioxo-4-(1,3-Thiazol-2-Yl)imidazolidin-4-Yl]methyl}-1-Benzofuran-2-Carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.81

Molecular Weight (Monoisotopic): 390.0190

AlogP: 2.01

#Rotatable Bonds: 4

Polar Surface Area: 113.33

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.44

CX Basic pKa: 1.83

CX LogP: 1.16

CX LogD: 1.12

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -1.32

References

1. Durham TB, Klimkowski VJ, Rito CJ, Marimuthu J, Toth JL, Liu C, Durbin JD, Stout SL, Adams L, Swearingen C, Lin C, Chambers MG, Thirunavukkarasu K, Wiley MR..  (2014)  Identification of potent and selective hydantoin inhibitors of aggrecanase-1 and aggrecanase-2 that are efficacious in both chemical and surgical models of osteoarthritis.,  57  (24): [PMID:25415648] [10.1021/jm501522n]

2. Wiley MR, Durham TB, Adams LA, Chambers MG, Lin C, Liu C, Marimuthu J, Mitchell PG, Mudra DR, Swearingen CA, Toth JL, Weller JM, Thirunavukkarasu K..  (2016)  Use of Osmotic Pumps to Establish the Pharmacokinetic-Pharmacodynamic Relationship and Define Desirable Human Performance Characteristics for Aggrecanase Inhibitors.,  59  (12): [PMID:27194201] [10.1021/acs.jmedchem.6b00398]

Source

Source(1):

• Scientific Literature