ID: ALA3912281

PubChem CID: 134132390

Max Phase: Preclinical

Molecular Formula: C23H22F3N7O3S

Molecular Weight: 533.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCCNS(=O)(=O)c2ncccc2CNc2nc(ncc2C(F)(F)F)Nc2ccc3c(c2)CCN13

Standard InChI:  InChI=1S/C23H22F3N7O3S/c24-23(25,26)17-13-29-22-31-16-5-6-18-14(11-16)7-10-33(18)19(34)4-2-9-30-37(35,36)21-15(3-1-8-27-21)12-28-20(17)32-22/h1,3,5-6,8,11,13,30H,2,4,7,9-10,12H2,(H2,28,29,31,32)

Standard InChI Key:  HIOYYLSBJMMPNZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  0  0  0  0  0  0999 V2000
   14.6682  -14.6352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2637  -13.9294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8547  -14.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1409  -10.2561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1397  -11.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8478  -11.4846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5575  -11.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5546  -10.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8460   -9.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2581   -9.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9006   -9.4671    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0574  -10.1418    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3912   -8.9978    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2658  -11.4827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2671  -12.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9754  -12.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9721  -13.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6796  -13.9293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3877  -13.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3838  -12.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6757  -12.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4304  -11.4851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0316  -12.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2151  -12.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0560  -13.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4511  -12.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2347  -13.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8132  -12.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0155  -13.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9438  -13.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6974  -14.2413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0335  -15.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1059  -14.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6993  -15.6530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5559  -14.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4835  -14.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2330  -13.7056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  8 10  1  0
  7 14  1  0
 14 15  1  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
  5 22  1  0
 22 23  1  0
 23 24  2  0
 24 28  1  0
 27 25  1  0
 25 26  2  0
 26 23  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 31 33  1  0
 33 34  2  0
 33 32  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 17  2  1  0
 37  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3912281

   ---

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: 533.54

Molecular Weight (Monoisotopic): 533.1457

AlogP: 3.21

#Rotatable Bonds: ┄

Polar Surface Area: 129.21

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.70

CX Basic pKa: 4.26

CX LogP: 2.41

CX LogD: 2.39

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.40

Np Likeness Score: -0.81

References

1. Farand J, Mai N, Chandrasekhar J, Newby ZE, Van Veldhuizen J, Loyer-Drew J, Venkataramani C, Guerrero J, Kwok A, Li N, Zherebina Y, Wilbert S, Zablocki J, Phillips G, Watkins WJ, Mourey R, Notte GT..  (2016)  Selectivity switch between FAK and Pyk2: Macrocyclization of FAK inhibitors improves Pyk2 potency.,  26  (24): [PMID:27876318] [10.1016/j.bmcl.2016.10.092]

Source

Source(1):

• Scientific Literature