isopropyl 2-cyano-6-(3-fluorobenzoyl)-4,4-dimethyl-1,4,5,6-tetrahydropyrrolo[3,2-d]azepine-8-carboxylate

ID: ALA578970

Chembl Id: CHEMBL578970

PubChem CID: 42601492

Max Phase: Preclinical

Molecular Formula: C22H22FN3O3

Molecular Weight: 395.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)C1=CN(C(=O)c2cccc(F)c2)CC(C)(C)c2cc(C#N)[nH]c21

Standard InChI:  InChI=1S/C22H22FN3O3/c1-13(2)29-21(28)17-11-26(20(27)14-6-5-7-15(23)8-14)12-22(3,4)18-9-16(10-24)25-19(17)18/h5-9,11,13,25H,12H2,1-4H3

Standard InChI Key:  ZYFPATDFWJXJGF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA578970

   Isopropyl 2-cyano-6-(3-fluorobenzoyl)-4,4-dimethyl-1,4,5,6-tetrahydropyrrolo[3,2-d]azepine-8-carboxylate

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: 395.43

Molecular Weight (Monoisotopic): 395.1645

AlogP: 3.75

#Rotatable Bonds: 3

Polar Surface Area: 86.19

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.18

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.80

Np Likeness Score: -0.63

References

1. Mehlmann JF, Crawley ML, Lundquist JT, Unwalla RJ, Harnish DC, Evans MJ, Kim CY, Wrobel JE, Mahaney PE..  (2009)  Pyrrole[2,3-d]azepino compounds as agonists of the farnesoid X receptor (FXR).,  19  (18): [PMID:19683924] [10.1016/j.bmcl.2009.07.148]

2. Xu Y..  (2016)  Recent Progress on Bile Acid Receptor Modulators for Treatment of Metabolic Diseases.,  59  (14): [PMID:26878262] [10.1021/acs.jmedchem.5b00342]

Source

Source(1):

• Scientific Literature