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2-[3-Cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-5-carboxylic acid methyl ester ID: ALA1094765
PubChem CID: 46221803
Max Phase: Preclinical
Molecular Formula: C19H20Cl2N2O3S
Molecular Weight: 427.35
Molecule Type: Small molecule
This compound is available for customization.
Associated Items:
Names and Identifiers Canonical SMILES: COC(=O)c1cnc(NC(=O)C(CC2CCCC2)c2ccc(Cl)c(Cl)c2)s1
Standard InChI: InChI=1S/C19H20Cl2N2O3S/c1-26-18(25)16-10-22-19(27-16)23-17(24)13(8-11-4-2-3-5-11)12-6-7-14(20)15(21)9-12/h6-7,9-11,13H,2-5,8H2,1H3,(H,22,23,24)
Standard InChI Key: GMIBWKKQKNUQRZ-UHFFFAOYSA-N
Molfile:
RDKit 2D
27 29 0 0 0 0 0 0 0 0999 V2000
0.9665 -8.7434 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
0.9133 -7.9161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.6829 -7.6169 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.2092 -8.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7666 -8.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0679 -9.7136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5551 -10.3619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8834 -9.8371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.2172 -7.4734 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.5150 -7.8561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5488 -8.6779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.2111 -7.4134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1750 -6.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9410 -7.7926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9770 -8.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7092 -9.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4053 -8.5579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.3692 -7.7326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.6371 -7.3498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1375 -8.9406 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
-2.7453 -9.8260 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
-0.4451 -6.2089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3216 -5.3934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4918 -5.2553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.8744 -5.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2966 -6.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3962 -9.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
2 3 2 0
3 4 1 0
4 5 2 0
1 5 1 0
6 7 2 0
6 8 1 0
5 6 1 0
10 11 2 0
10 12 1 0
12 13 1 0
14 15 1 0
15 16 2 0
16 17 1 0
17 18 2 0
18 19 1 0
14 19 2 0
17 20 1 0
16 21 1 0
12 14 1 0
9 10 1 0
22 23 1 0
23 24 1 0
24 25 1 0
25 26 1 0
22 26 1 0
13 22 1 0
2 9 1 0
8 27 1 0
M END Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 427.35Molecular Weight (Monoisotopic): 426.0572AlogP: 5.54#Rotatable Bonds: 6Polar Surface Area: 68.29Molecular Species: NEUTRALHBA: 5HBD: 1#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski): 1CX Acidic pKa: 7.74CX Basic pKa: ┄CX LogP: 5.88CX LogD: 5.72Aromatic Rings: 2Heavy Atoms: 27QED Weighted: 0.62Np Likeness Score: -1.13
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 ]