US8952169, 64

ID: ALA3657855

Chembl Id: CHEMBL3657855

Cas Number: 1494581-70-2

PubChem CID: 91809347

Max Phase: Preclinical

Molecular Formula: C24H31FN2O4S

Molecular Weight: 462.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NS(=O)(=O)N1CCC1)c1cc(C2CC2)c(OCC23CC4CC(CC(C4)C2)C3)cc1F

Standard InChI:  InChI=1S/C24H31FN2O4S/c25-21-10-22(31-14-24-11-15-6-16(12-24)8-17(7-15)13-24)19(18-2-3-18)9-20(21)23(28)26-32(29,30)27-4-1-5-27/h9-10,15-18H,1-8,11-14H2,(H,26,28)

Standard InChI Key:  PTCBNPULJWGSML-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3657855

   4-(1-adamantylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

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: 462.59

Molecular Weight (Monoisotopic): 462.1989

AlogP: 3.98

#Rotatable Bonds: 7

Polar Surface Area: 75.71

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.05

CX Basic pKa: ┄

CX LogP: 3.38

CX LogD: 2.44

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.67

Np Likeness Score: -0.85

References

1.  (2015)  N-substituted benzamides and methods of use thereof, 

2. McKerrall SJ, Sutherlin DP..  (2018)  Nav1.7 inhibitors for the treatment of chronic pain.,  28  (19): [PMID:30139550] [10.1016/j.bmcl.2018.08.007]

3. Mulcahy JV, Pajouhesh H, Beckley JT, Delwig A, Du Bois J, Hunter JC..  (2019)  Challenges and Opportunities for Therapeutics Targeting the Voltage-Gated Sodium Channel Isoform Na_V1.7.,  62  (19): [PMID:31012583] [10.1021/acs.jmedchem.8b01906]

4. Safina BS, McKerrall SJ, Sun S, Chen CA, Chowdhury S, Jia Q, Li J, Zenova AY, Andrez JC, Bankar G, Bergeron P, Chang JH, Chang E, Chen J, Dean R, Decker SM, DiPasquale A, Focken T, Hemeon I, Khakh K, Kim A, Kwan R, Lindgren A, Lin S, Maher J, Mezeyova J, Misner D, Nelkenbrecher K, Pang J, Reese R, Shields SD, Sojo L, Sheng T, Verschoof H, Waldbrook M, Wilson MS, Xie Z, Young C, Zabka TS, Hackos DH, Ortwine DF, White AD, Johnson JP, Robinette CL, Dehnhardt CM, Cohen CJ, Sutherlin DP..  (2021)  Discovery of Acyl-sulfonamide Na_v1.7 Inhibitors GDC-0276 and GDC-0310.,  64  (6.0): [PMID:33682420] [10.1021/acs.jmedchem.1c00049]

5. Karanjule N, Hayashi N, Suzuki S, Tsuda T, Tokumaru E, Tanaka K, Kimoto H, Domon Y, Takahashi S, Kubota K, Kitano Y, Yokoyama T, Koishi R, Fujiwara C, Inaba S, Asano D, Sakakura T, Takasuna K, Shinozuka T..  (2023)  N-Aryl Indoles as a Novel Class of Potent Na_V1.7 Inhibitors.,  14  (6): [PMID:37312847] [10.1021/acsmedchemlett.3c00079]

6. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

Source

Source(3):

• Scientific Literature
• BindingDB Database
• EUbOPEN Chemogenomic Library