ID: ALA576138

Max Phase: Preclinical

Molecular Formula: C19H16Cl2N2O2

Molecular Weight: 375.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1ccc(N(C)C(=O)c2c(-c3ccccc3Cl)noc2C)cc1Cl

Standard InChI:  InChI=1S/C19H16Cl2N2O2/c1-11-8-9-13(10-16(11)21)23(3)19(24)17-12(2)25-22-18(17)14-6-4-5-7-15(14)20/h4-10H,1-3H3

Standard InChI Key:  WRRGABWWSIAMMJ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 375.26

Molecular Weight (Monoisotopic): 374.0589

AlogP: 5.54

#Rotatable Bonds: 3

Polar Surface Area: 46.34

Molecular Species: NEUTRAL

HBA: 3

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -1.85

References

1. Evans KA, Budzik BW, Ross SA, Wisnoski DD, Jin J, Rivero RA, Vimal M, Szewczyk GR, Jayawickreme C, Moncol DL, Rimele TJ, Armour SL, Weaver SP, Griffin RJ, Tadepalli SM, Jeune MR, Shearer TW, Chen ZB, Chen L, Anderson DL, Becherer JD, De Los Frailes M, Colilla FJ..  (2009)  Discovery of 3-aryl-4-isoxazolecarboxamides as TGR5 receptor agonists.,  52  (24): [PMID:19902954] [10.1021/jm901434t]

2. Budzik BW, Evans KA, Wisnoski DD, Jin J, Rivero RA, Szewczyk GR, Jayawickreme C, Moncol DL, Yu H..  (2010)  Synthesis and structure-activity relationships of a series of 3-aryl-4-isoxazolecarboxamides as a new class of TGR5 agonists.,  20  (4): [PMID:20097073] [10.1016/j.bmcl.2010.01.003]

3. Piotrowski DW, Futatsugi K, Warmus JS, Orr ST, Freeman-Cook KD, Londregan AT, Wei L, Jennings SM, Herr M, Coffey SB, Jiao W, Storer G, Hepworth D, Wang J, Lavergne SY, Chin JE, Hadcock JR, Brenner MB, Wolford AC, Janssen AM, Roush NS, Buxton J, Hinchey T, Kalgutkar AS, Sharma R, Flynn DA..  (2013)  Identification of Tetrahydropyrido[4,3-d]pyrimidine Amides as a New Class of Orally Bioavailable TGR5 Agonists.,  4  (1): [PMID:24900564] [10.1021/ml300277t]

4. Londregan AT, Piotrowski DW, Futatsugi K, Warmus JS, Boehm M, Carpino PA, Chin JE, Janssen AM, Roush NS, Buxton J, Hinchey T..  (2013)  Discovery of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as potent agonists of TGR5 via sequential combinatorial libraries.,  23  (5): [PMID:23337601] [10.1016/j.bmcl.2012.12.076]

Source

Source(1):

• Scientific Literature