trans-4-(4-{6-[(2S)-2-{[2-(4-Cyanophenyl)ethyl]carbamoyl}azetidin-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl}phenyl)cyclohexane-1-carboxylic Acid

ID: ALA3234871

Chembl Id: CHEMBL3234871

Cas Number: 1595145-44-0

PubChem CID: 90654600

Max Phase: Preclinical

Molecular Formula: C31H30F3N5O3

Molecular Weight: 577.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(CCNC(=O)[C@@H]2CCN2c2cc(-c3ccc([C@H]4CC[C@H](C(=O)O)CC4)cc3)nc(C(F)(F)F)n2)cc1

Standard InChI:  InChI=1S/C31H30F3N5O3/c32-31(33,34)30-37-25(23-9-5-21(6-10-23)22-7-11-24(12-8-22)29(41)42)17-27(38-30)39-16-14-26(39)28(40)36-15-13-19-1-3-20(18-35)4-2-19/h1-6,9-10,17,22,24,26H,7-8,11-16H2,(H,36,40)(H,41,42)/t22-,24-,26-/m0/s1

Standard InChI Key:  DDAWTSCZLAACFR-GVUKDKGQSA-N

Alternative Forms

1. Parent:

   

   ALA3234871

   4-[4-[6-[(2S)-2-[2-(4-cyanophenyl)ethylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl]phenyl]cyclohexane-1-carboxylic acid

2. Alternative Forms:

   

   ALA3234871

   4-[4-[6-[(2S)-2-[2-(4-cyanophenyl)ethylcarbamoyl]azetidin-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl]phenyl]cyclohexane-1-carboxylic acid;(2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol

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: 577.61

Molecular Weight (Monoisotopic): 577.2301

AlogP: 5.33

#Rotatable Bonds: 8

Polar Surface Area: 119.21

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.81

CX Basic pKa: 1.95

CX LogP: 6.67

CX LogD: 4.12

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.37

Np Likeness Score: -1.01

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