(+/-)-5-[({trans-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethylpiperazin-1-yl}carbonyl)amino]pyridine-2-carboxylic acid

ID: ALA201314

Chembl Id: CHEMBL201314

PubChem CID: 11554146

Max Phase: Preclinical

Molecular Formula: C21H20F3N5O3

Molecular Weight: 447.42

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(C(=O)O)nc1

Standard InChI:  InChI=1S/C21H20F3N5O3/c1-12-11-29(20(32)27-15-4-6-18(19(30)31)26-9-15)13(2)10-28(12)16-5-3-14(8-25)17(7-16)21(22,23)24/h3-7,9,12-13H,10-11H2,1-2H3,(H,27,32)(H,30,31)/t12-,13+/m0/s1

Standard InChI Key:  JYDQXQCRXOXJBJ-QWHCGFSZSA-N

Alternative Forms

1. Parent:

   

   ALA201314

   5-[[(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethylpiperazine-1-carbonyl]amino]pyridine-2-carboxylic acid

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: 447.42

Molecular Weight (Monoisotopic): 447.1518

AlogP: 3.80

#Rotatable Bonds: 3

Polar Surface Area: 109.56

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.11

CX Basic pKa: 5.12

CX LogP: 2.24

CX LogD: 0.25

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.74

Np Likeness Score: -1.58

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