(R)-N-(4-Cyanophenethyl)-1-(6-(piperazin-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)piperidine-3-carboxamide

ID: ALA3234569

Chembl Id: CHEMBL3234569

PubChem CID: 90654588

Max Phase: Preclinical

Molecular Formula: C24H28F3N7O

Molecular Weight: 487.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(CCNC(=O)[C@@H]2CCCN(c3cc(N4CCNCC4)nc(C(F)(F)F)n3)C2)cc1

Standard InChI:  InChI=1S/C24H28F3N7O/c25-24(26,27)23-31-20(33-12-9-29-10-13-33)14-21(32-23)34-11-1-2-19(16-34)22(35)30-8-7-17-3-5-18(15-28)6-4-17/h3-6,14,19,29H,1-2,7-13,16H2,(H,30,35)/t19-/m1/s1

Standard InChI Key:  UKDXGNZPPKPUKO-LJQANCHMSA-N

Alternative Forms

1. Parent:

   

   ALA3234569

   (3R)-N-[2-(4-cyanophenyl)ethyl]-1-[6-piperazin-1-yl-2-(trifluoromethyl)pyrimidin-4-yl]piperidine-3-carboxamide

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: 487.53

Molecular Weight (Monoisotopic): 487.2307

AlogP: 2.35

#Rotatable Bonds: 6

Polar Surface Area: 97.18

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.75

CX LogP: 4.20

CX LogD: 2.83

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.65

Np Likeness Score: -1.70

References

1. Phillips DP, Gao W, Yang Y, Zhang G, Lerario IK, Lau TL, Jiang J, Wang X, Nguyen DG, Bhat BG, Trotter C, Sullivan H, Welzel G, Landry J, Chen Y, Joseph SB, Li C, Gordon WP, Richmond W, Johnson K, Bretz A, Bursulaya B, Pan S, McNamara P, Seidel HM..  (2014)  Discovery of trifluoromethyl(pyrimidin-2-yl)azetidine-2-carboxamides as potent, orally bioavailable TGR5 (GPBAR1) agonists: structure-activity relationships, lead optimization, and chronic in vivo efficacy.,  57  (8): [PMID:24666203] [10.1021/jm401731q]

Source

Source(1):

• Scientific Literature