US9212182, 672

ID: ALA3979498

Chembl Id: CHEMBL3979498

PubChem CID: 117749324

Max Phase: Preclinical

Molecular Formula: C27H19F3N4O4S

Molecular Weight: 552.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2cccc(C(F)(F)F)c2)ccc1-n1c(=O)ccc2cc(S(=O)(=O)Nc3ncccn3)ccc21

Standard InChI:  InChI=1S/C27H19F3N4O4S/c1-38-24-16-18(17-4-2-5-20(14-17)27(28,29)30)6-9-23(24)34-22-10-8-21(15-19(22)7-11-25(34)35)39(36,37)33-26-31-12-3-13-32-26/h2-16H,1H3,(H,31,32,33)

Standard InChI Key:  HSOCYPPAQYZHMJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3979498

   1-[2-methoxy-4-[3-(trifluoromethyl)phenyl]phenyl]-2-oxo-N-pyrimidin-2-ylquinoline-6-sulfonamide

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: 552.53

Molecular Weight (Monoisotopic): 552.1079

AlogP: 5.28

#Rotatable Bonds: 6

Polar Surface Area: 103.18

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.86

CX Basic pKa: ┄

CX LogP: 4.73

CX LogD: 4.23

Aromatic Rings: 5

Heavy Atoms: 39

QED Weighted: 0.31

Np Likeness Score: -1.46

References

1.  (2015)  Bicyclic sulfonamide compounds as sodium channel inhibitors, 

2. Graceffa RF, Boezio AA, Able J, Altmann S, Berry LM, Boezio C, Butler JR, Chu-Moyer M, Cooke M, DiMauro EF, Dineen TA, Feric Bojic E, Foti RS, Fremeau RT, Guzman-Perez A, Gao H, Gunaydin H, Huang H, Huang L, Ilch C, Jarosh M, Kornecook T, Kreiman CR, La DS, Ligutti J, Milgram BC, Lin MJ, Marx IE, Nguyen HN, Peterson EA, Rescourio G, Roberts J, Schenkel L, Shimanovich R, Sparling BA, Stellwagen J, Taborn K, Vaida KR, Wang J, Yeoman J, Yu V, Zhu D, Moyer BD, Weiss MM..  (2017)  Sulfonamides as Selective NaV1.7 Inhibitors: Optimizing Potency, Pharmacokinetics, and Metabolic Properties to Obtain Atropisomeric Quinolinone (AM-0466) that Affords Robust in Vivo Activity.,  60  (14): [PMID:28324649] [10.1021/acs.jmedchem.6b01850]

3. Schenkel LB, DiMauro EF, Nguyen HN, Chakka N, Du B, Foti RS, Guzman-Perez A, Jarosh M, La DS, Ligutti J, Milgram BC, Moyer BD, Peterson EA, Roberts J, Yu VL, Weiss MM..  (2017)  Discovery of a biarylamide series of potent, state-dependent NaV1.7 inhibitors.,  27  (16): [PMID:28684121] [10.1016/j.bmcl.2017.06.054]

Source

Source(2):

• Scientific Literature
• BindingDB Database