N-(3-chloro-4-methylphenyl)-3-(2-chlorophenyl)-N,5-dimethylisoxazole-4-carboxamide

ID: ALA576138

Chembl Id: CHEMBL576138

Cas Number: 1197300-25-6

PubChem CID: 44605617

Max Phase: Preclinical

Molecular Formula: C19H16Cl2N2O2

Molecular Weight: 375.26

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

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

Associated Targets(Human)

GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U2OS (164939 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Gpbar1 G-protein coupled bile acid receptor 1 (5 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Melanophore (216 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatocyte (2621 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Canis familiaris (36305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 375.26Molecular Weight (Monoisotopic): 374.0589AlogP: 5.54#Rotatable Bonds: 3
Polar Surface Area: 46.34Molecular Species: NEUTRALHBA: 3HBD:
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 5.25CX LogD: 5.25
Aromatic Rings: 3Heavy Atoms: 25QED Weighted: 0.60Np 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.,  (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