(+/-)-tert-Butyl {5-[({trans-4-[4-cyano-3-(trifluoromethyl)-phenyl]-2,5-dimethylpiperazin-1-yl}carbonyl)amino]pyridin-2-yl}-carbamate

ID: ALA201488

Chembl Id: CHEMBL201488

PubChem CID: 11706261

Max Phase: Preclinical

Molecular Formula: C25H29F3N6O3

Molecular Weight: 518.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CN(c2ccc(C#N)c(C(F)(F)F)c2)[C@@H](C)CN1C(=O)Nc1ccc(NC(=O)OC(C)(C)C)nc1

Standard InChI:  InChI=1S/C25H29F3N6O3/c1-15-14-34(16(2)13-33(15)19-8-6-17(11-29)20(10-19)25(26,27)28)22(35)31-18-7-9-21(30-12-18)32-23(36)37-24(3,4)5/h6-10,12,15-16H,13-14H2,1-5H3,(H,31,35)(H,30,32,36)/t15-,16+/m0/s1

Standard InChI Key:  UIGYJVXIWABWNG-JKSUJKDBSA-N

Alternative Forms

1. Parent:

   

   ALA201488

   tert-butyl N-[5-[[(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethylpiperazine-1-carbonyl]amino]pyridin-2-yl]carbamate

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: 518.54

Molecular Weight (Monoisotopic): 518.2253

AlogP: 5.45

#Rotatable Bonds: 3

Polar Surface Area: 110.59

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.60

CX Basic pKa: 2.74

CX LogP: 4.92

CX LogD: 4.92

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.56

Np Likeness Score: -1.71

References

1. Kinoyama I, Taniguchi N, Toyoshima A, Nozawa E, Kamikubo T, Imamura M, Matsuhisa A, Samizu K, Kawanimani E, Niimi T, Hamada N, Koutoku H, Furutani T, Kudoh M, Okada M, Ohta M, Tsukamoto S..  (2006)  (+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3- yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist.,  49  (2): [PMID:16420057] [10.1021/jm050293c]

Source

Source(1):

• Scientific Literature