1-[3-Cyclopentyl-2(S)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-urea

ID: ALA1094749

PubChem CID: 46222021

Max Phase: Preclinical

Molecular Formula: C16H20Cl2N2O2

Molecular Weight: 343.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)NC(=O)[C@@H](CC1CCCC1)c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C16H20Cl2N2O2/c1-19-16(22)20-15(21)12(8-10-4-2-3-5-10)11-6-7-13(17)14(18)9-11/h6-7,9-10,12H,2-5,8H2,1H3,(H2,19,20,21,22)/t12-/m0/s1

Standard InChI Key:  IPFOWEUMNGCEDZ-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    0.3852   -6.9923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0928   -7.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838   -8.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114   -7.0066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224   -6.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334   -7.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3445   -8.2178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0431   -6.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341   -6.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616   -7.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707   -8.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -8.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989   -8.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899   -7.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713   -6.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174   -8.5891    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -9.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3154   -5.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2152   -4.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921   -4.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958   -5.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381   -6.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  6
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 13 16  1  0
 12 17  1  0
  8 10  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 18 22  1  0
  9 18  1  0
  1  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094749

   (2S)-3-cyclopentyl-2-(3,4-dichlorophenyl)-N-(methylcarbamoyl)propanamide

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: 343.25

Molecular Weight (Monoisotopic): 342.0902

AlogP: 4.11

#Rotatable Bonds: 4

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.88

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -0.74

References

1. 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]

Source

Source(1):

• Scientific Literature