ID: ALA2325622

Max Phase: Preclinical

Molecular Formula: C21H17ClF2N6O3S2

Molecular Weight: 538.99

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN1CC(n2nccc2-c2cc(Cl)ccc2Oc2cc(F)c(S(=O)(=O)Nc3ncns3)cc2F)C1

Standard InChI:  InChI=1S/C21H17ClF2N6O3S2/c1-29-9-13(10-29)30-17(4-5-26-30)14-6-12(22)2-3-18(14)33-19-7-16(24)20(8-15(19)23)35(31,32)28-21-25-11-27-34-21/h2-8,11,13H,9-10H2,1H3,(H,25,27,28)

Standard InChI Key:  QESPTBXFDDSHIF-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: 538.99

Molecular Weight (Monoisotopic): 538.0460

AlogP: 4.41

#Rotatable Bonds: 7

Polar Surface Area: 102.24

Molecular Species: ACID

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.34

CX Basic pKa: 7.08

CX LogP: 2.99

CX LogD: 2.96

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -1.65

References

1. Norinder U, Ek ME..  (2013)  QSAR investigation of NaV1.7 active compounds using the SVM/Signature approach and the Bioclipse Modeling platform.,  23  (1): [PMID:23177785] [10.1016/j.bmcl.2012.10.102]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

3. Swain NA, Batchelor D, Beaudoin S, Bechle BM, Bradley PA, Brown AD, Brown B, Butcher KJ, Butt RP, Chapman ML, Denton S, Ellis D, Galan SRG, Gaulier SM, Greener BS, de Groot MJ, Glossop MS, Gurrell IK, Hannam J, Johnson MS, Lin Z, Markworth CJ, Marron BE, Millan DS, Nakagawa S, Pike A, Printzenhoff D, Rawson DJ, Ransley SJ, Reister SM, Sasaki K, Storer RI, Stupple PA, West CW..  (2017)  Discovery of Clinical Candidate 4-[2-(5-Amino-1H-pyrazol-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-N-1,3-thiazol-4-ylbenzenesulfonamide (PF-05089771): Design and Optimization of Diaryl Ether Aryl Sulfonamides as Selective Inhibitors of NaV1.7.,  60  (16): [PMID:28682065] [10.1021/acs.jmedchem.7b00598]

4. Shinozuka T, Kobayashi H, Suzuki S, Tanaka K, Karanjule N, Hayashi N, Tsuda T, Tokumaru E, Inoue M, Ueda K, Kimoto H, Domon Y, Takahashi S, Kubota K, Yokoyama T, Shimizugawa A, Koishi R, Fujiwara C, Asano D, Sakakura T, Takasuna K, Abe Y, Watanabe T, Kitano Y..  (2020)  Discovery of DS-1971a, a Potent, Selective Na_V1.7 Inhibitor.,  63  (18): [PMID:32392056] [10.1021/acs.jmedchem.0c00259]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data