ID: ALA359618

Max Phase: Preclinical

Molecular Formula: C18H22N2O3S2

Molecular Weight: 378.52

Molecule Type: Small molecule

Representations

Canonical SMILES:  CS(=O)(=O)c1ccc(C(CC2CCCC2)C(=O)Nc2nccs2)cc1

Standard InChI:  InChI=1S/C18H22N2O3S2/c1-25(22,23)15-8-6-14(7-9-15)16(12-13-4-2-3-5-13)17(21)20-18-19-10-11-24-18/h6-11,13,16H,2-5,12H2,1H3,(H,19,20,21)

Standard InChI Key:  NEQSWPCDHDQINX-UHFFFAOYSA-N

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

Properties

Molecular Weight: 378.52

Molecular Weight (Monoisotopic): 378.1072

AlogP: 3.85

#Rotatable Bonds: 6

Polar Surface Area: 76.13

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.89

CX Basic pKa:

CX LogP: 3.37

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -1.36

References

1. Castelhano AL, Dong H, Fyfe MC, Gardner LS, Kamikozawa Y, Kurabayashi S, Nawano M, Ohashi R, Procter MJ, Qiu L, Rasamison CM, Schofield KL, Shah VK, Ueta K, Williams GM, Witter D, Yasuda K..  (2005)  Glucokinase-activating ureas.,  15  (5): [PMID:15713416] [10.1016/j.bmcl.2004.12.083]

2. Haynes NE, Corbett WL, Bizzarro FT, Guertin KR, Hilliard DW, Holland GW, Kester RF, Mahaney PE, Qi L, Spence CL, Tengi J, Dvorozniak MT, Railkar A, Matschinsky FM, Grippo JF, Grimsby J, Sarabu R..  (2010)  Discovery, structure-activity relationships, pharmacokinetics, and efficacy of glucokinase activator (2R)-3-cyclopentyl-2-(4-methanesulfonylphenyl)-N-thiazol-2-yl-propionamide (RO0281675).,  53  (9): [PMID:20405948] [10.1021/jm100039a]

3. Sarabu R, Bizzarro FT, Corbett WL, Dvorozniak MT, Geng W, Grippo JF, Haynes NE, Hutchings S, Garofalo L, Guertin KR, Hilliard DW, Kabat M, Kester RF, Ka W, Liang Z, Mahaney PE, Marcus L, Matschinsky FM, Moore D, Racha J, Radinov R, Ren Y, Qi L, Pignatello M, Spence CL, Steele T, Tengi J, Grimsby J..  (2012)  Discovery of piragliatin--first glucokinase activator studied in type 2 diabetic patients.,  55  (16): [PMID:22809456] [10.1021/jm3008689]

4. Li Y, Tian K, Qin A, Zhang L, Huo L, Lei L, Shen Z, Song H, Feng Z..  (2014)  Discovery of novel urea derivatives as dual-target hypoglycemic agents that activate glucokinase and PPARγ.,  76  [PMID:24583379] [10.1016/j.ejmech.2014.02.024]

Source

Source(1):

• Scientific Literature