2-((2-Chloro-6-fluorophenyl)amino)-N-(3-fluoro-5-(trifluoromethyl)phenyl)-1-methyl-7,8-dihydro-1H-[1,4]dioxino[2',3':3,4]benzo[1,2-d]imidazole-5-carboxamide

ID: ALA3897959

Chembl Id: CHEMBL3897959

Cas Number: 1469976-70-2

PubChem CID: 71766070

Max Phase: Preclinical

Molecular Formula: C24H16ClF5N4O3

Molecular Weight: 538.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(Nc2c(F)cccc2Cl)nc2cc(C(=O)Nc3cc(F)cc(C(F)(F)F)c3)c3c(c21)OCCO3

Standard InChI:  InChI=1S/C24H16ClF5N4O3/c1-34-19-17(32-23(34)33-18-15(25)3-2-4-16(18)27)10-14(20-21(19)37-6-5-36-20)22(35)31-13-8-11(24(28,29)30)7-12(26)9-13/h2-4,7-10H,5-6H2,1H3,(H,31,35)(H,32,33)

Standard InChI Key:  HOTSVKDMIYWWIY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3897959

   mPGES1-IN-3

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: 538.86

Molecular Weight (Monoisotopic): 538.0831

AlogP: 6.29

#Rotatable Bonds: 4

Polar Surface Area: 77.41

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.22

CX Basic pKa: 5.86

CX LogP: 5.98

CX LogD: 5.97

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.30

Np Likeness Score: -1.61

References

1. Muthukaman N, Deshmukh S, Sarode N, Tondlekar S, Tambe M, Pisal D, Shaikh M, Kattige VG, Honnegowda S, Karande V, Kulkarni A, Jadhav SB, Mahat MYA, Gudi GS, Khairatkar-Joshi N, Gharat LA..  (2016)  Discovery of 2-((2-chloro-6-fluorophenyl)amino)-N-(3-fluoro-5-(trifluoromethyl)phenyl)-1-methyl-7,8-dihydro-1H-[1,4]dioxino[2',3':3,4]benzo[1,2-d]imidazole-5-carboxamide as potent, selective and efficacious microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitor.,  26  (24): [PMID:27865703] [10.1016/j.bmcl.2016.10.079]

Source

Source(1):

• Scientific Literature