1-(2-Chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)-N-(isoxazol-3-yl)-3-methyl-4-oxo-3,4-dihydrophthalazine-6-sulfonamide

ID: ALA4097970

PubChem CID: 117741784

Max Phase: Preclinical

Molecular Formula: C25H18ClFN4O5S

Molecular Weight: 540.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2cccc(F)c2)c(Cl)cc1-c1nn(C)c(=O)c2cc(S(=O)(=O)Nc3ccon3)ccc12

Standard InChI:  InChI=1S/C25H18ClFN4O5S/c1-31-25(32)19-11-16(37(33,34)30-23-8-9-36-29-23)6-7-17(19)24(28-31)20-12-21(26)18(13-22(20)35-2)14-4-3-5-15(27)10-14/h3-13H,1-2H3,(H,29,30)

Standard InChI Key:  HIEJKXMLHXPHRC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   29.3463   -6.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8221   -6.1560    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.0090   -6.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1026   -4.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8148   -5.3385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5362   -6.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5400   -7.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9436   -6.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2317   -6.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9554   -7.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2525   -7.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2576   -8.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9640   -8.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6670   -8.5715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6635   -7.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3680   -7.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0775   -7.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7816   -7.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.0599   -6.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3588   -6.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4797   -6.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0813   -8.5661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3754   -8.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1874   -6.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8909   -6.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8840   -5.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1677   -4.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4671   -5.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1574   -4.0569    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.0508   -5.2975    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.0109   -4.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2097   -3.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8090   -4.6789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3627   -5.2799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9680   -9.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5519   -8.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  2  1  0
  2  6  1  0
  6  7  2  0
  7 11  1  0
 10  8  1  0
  8  9  2  0
  9  6  1  0
 10 11  2  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 17 23  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 22  1  0
 28 30  1  0
 20 31  1  0
  4 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 35  4  2  0
 13 36  1  0
 12 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097970

   US9776995, Example 21

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: 540.96

Molecular Weight (Monoisotopic): 540.0670

AlogP: 4.86

#Rotatable Bonds: 6

Polar Surface Area: 116.32

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.73

CX Basic pKa: ┄

CX LogP: 4.64

CX LogD: 3.77

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: -1.58

References

1. Weiss MM, Dineen TA, Marx IE, Altmann S, Boezio A, Bregman H, Chu-Moyer M, DiMauro EF, Feric Bojic E, Foti RS, Gao H, Graceffa R, Gunaydin H, Guzman-Perez A, Huang H, Huang L, Jarosh M, Kornecook T, Kreiman CR, Ligutti J, La DS, Lin MJ, Liu D, Moyer BD, Nguyen HN, Peterson EA, Rose PE, Taborn K, Youngblood BD, Yu V, Fremeau RT..  (2017)  Sulfonamides as Selective NaV1.7 Inhibitors: Optimizing Potency and Pharmacokinetics While Mitigating Metabolic Liabilities.,  60  (14): [PMID:28287723] [10.1021/acs.jmedchem.6b01851]

Source

Source(1):

• Scientific Literature