ID: ALA211564

Max Phase: Preclinical

Molecular Formula: C27H33Cl2F3N4O2

Molecular Weight: 573.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)C[C@H](NC(=O)CN)c1cc(C(F)(F)F)ccc1N1CCN(C(=O)CCc2ccc(Cl)cc2Cl)CC1

Standard InChI:  InChI=1S/C27H33Cl2F3N4O2/c1-17(2)13-23(34-25(37)16-33)21-14-19(27(30,31)32)5-7-24(21)35-9-11-36(12-10-35)26(38)8-4-18-3-6-20(28)15-22(18)29/h3,5-7,14-15,17,23H,4,8-13,16,33H2,1-2H3,(H,34,37)/t23-/m0/s1

Standard InChI Key:  JKCHNCUBXBYAJL-QHCPKHFHSA-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: 573.49

Molecular Weight (Monoisotopic): 572.1933

AlogP: 5.46

#Rotatable Bonds: 9

Polar Surface Area: 78.67

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.29

CX Basic pKa: 8.14

CX LogP: 5.21

CX LogD: 4.40

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.42

Np Likeness Score: -1.30

References

1. Jiang W, Tucci FC, Chen CW, Arellano M, Tran JA, White NS, Marinkovic D, Pontillo J, Fleck BA, Wen J, Saunders J, Madan A, Foster AC, Chen C..  (2006)  Arylpropionylpiperazines as antagonists of the human melanocortin-4 receptor.,  16  (17): [PMID:16777413] [10.1016/j.bmcl.2006.05.088]

2. Tran JA, Jiang W, Tucci FC, Fleck BA, Wen J, Sai Y, Madan A, Chen TK, Markison S, Foster AC, Hoare SR, Marks D, Harman J, Chen CW, Arellano M, Marinkovic D, Bozigian H, Saunders J, Chen C..  (2007)  Design, synthesis, in vitro, and in vivo characterization of phenylpiperazines and pyridinylpiperazines as potent and selective antagonists of the melanocortin-4 receptor.,  50  (25): [PMID:17994683] [10.1021/jm701137s]

Source

Source(1):

• Scientific Literature