2-(R)-Cyclohexyl-N-(2-{4-[5-(2,3-dichloro-phenyl)-2H-pyrazol-3-yl]-piperidin-1-yl}-2-oxo-ethyl)-2-guanidino-acetamide

ID: ALA106187

Chembl Id: CHEMBL106187

PubChem CID: 447945

Max Phase: Preclinical

Molecular Formula: C25H33Cl2N7O2

Molecular Weight: 534.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)N[C@@H](C(=O)NCC(=O)N1CCC(c2cc(-c3cccc(Cl)c3Cl)n[nH]2)CC1)C1CCCCC1

Standard InChI:  InChI=1S/C25H33Cl2N7O2/c26-18-8-4-7-17(22(18)27)20-13-19(32-33-20)15-9-11-34(12-10-15)21(35)14-30-24(36)23(31-25(28)29)16-5-2-1-3-6-16/h4,7-8,13,15-16,23H,1-3,5-6,9-12,14H2,(H,30,36)(H,32,33)(H4,28,29,31)/t23-/m1/s1

Standard InChI Key:  SSSXBBASYYVGCI-HSZRJFAPSA-N

Alternative Forms

1. Parent:

   

   ALA106187

   2-Cyclohexyl-N-(2-{4-[5-(2,3-dichloro-phenyl)-2H-pyrazol-3-YL]-piperidin-1-YL}-2-oxo-ethyl)-2-guanidino-acetamide

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: 534.49

Molecular Weight (Monoisotopic): 533.2073

AlogP: 3.64

#Rotatable Bonds: 7

Polar Surface Area: 139.99

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.85

CX Basic pKa: 11.42

CX LogP: 2.89

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: -1.24

References

1. Raimundo BC, Oslob JD, Braisted AC, Hyde J, McDowell RS, Randal M, Waal ND, Wilkinson J, Yu CH, Arkin MR..  (2004)  Integrating fragment assembly and biophysical methods in the chemical advancement of small-molecule antagonists of IL-2: an approach for inhibiting protein-protein interactions.,  47  (12): [PMID:15163192] [10.1021/jm049967u]

2. Waal ND, Yang W, Oslob JD, Arkin MR, Hyde J, Lu W, McDowell RS, Yu CH, Raimundo BC..  (2005)  Identification of nonpeptidic small-molecule inhibitors of interleukin-2.,  15  (4): [PMID:15686897] [10.1016/j.bmcl.2004.12.045]

3. Kalsoom S, Rashid U, Shaukat A, Abdalla OM, Hussain K, Khan W, Nazir S, Mesaik MA, Zaheer-ul-Haq, Ansari FL.  (2013)  In vitro and in silico exploration of IL-2 inhibition by small drug-like molecules,  22  (12): [10.1007/s00044-013-0564-x]

Source

Source(1):

• Scientific Literature