(rac)-4-(1-(5,8-Difluoroquinolin-4-yl)-2-methyl-4-(4H-1,2,4-triazol-3-yl)-1H-benzo[d]imidazol-6-yl)-3-fluoropyridin-2-amine

ID: ALA4470860

PubChem CID: 134372959

Max Phase: Preclinical

Molecular Formula: C24H15F3N8

Molecular Weight: 472.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc2c(-c3nnc[nH]3)cc(-c3ccnc(N)c3F)cc2n1-c1ccnc2c(F)ccc(F)c12

Standard InChI:  InChI=1S/C24H15F3N8/c1-11-33-21-14(24-31-10-32-34-24)8-12(13-4-6-30-23(28)20(13)27)9-18(21)35(11)17-5-7-29-22-16(26)3-2-15(25)19(17)22/h2-10H,1H3,(H2,28,30)(H,31,32,34)

Standard InChI Key:  SBVBUGSOYHJGGD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 40  0  0  0  0  0  0  0  0999 V2000
    6.4968  -15.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2139  -15.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2110  -14.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4951  -14.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7814  -15.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7781  -14.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924  -14.3760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5101  -15.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9979  -15.7108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5016  -16.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8336  -17.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0886  -17.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9143  -17.9624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1695  -17.1771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351  -13.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201  -12.0258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299  -13.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6713  -12.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9215  -14.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6384  -14.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3514  -14.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3487  -13.3773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6271  -12.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9170  -13.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6407  -15.4444    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0678  -14.6144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -12.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2844  -12.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0872  -13.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6356  -12.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3756  -11.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735  -11.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3444  -13.9294    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137  -10.8009    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844  -15.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  1 10  1  0
 15 28  2  0
 27 16  2  0
 16 18  1  0
 17 15  1  0
  7 15  1  0
 17 18  2  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  3 19  1  0
 20 25  1  0
 21 26  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 29 33  1  0
 32 34  1  0
  8 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4470860

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.43

Molecular Weight (Monoisotopic): 472.1372

AlogP: 4.73

#Rotatable Bonds: 3

Polar Surface Area: 111.19

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.53

CX Basic pKa: 5.08

CX LogP: 2.99

CX LogD: 2.98

Aromatic Rings: 6

Heavy Atoms: 35

QED Weighted: 0.39

Np Likeness Score: -0.83

References

1. Chandrasekhar J, Dick R, Van Veldhuizen J, Koditek D, Lepist EI, McGrath ME, Patel L, Phillips G, Sedillo K, Somoza JR, Therrien J, Till NA, Treiberg J, Villaseñor AG, Zherebina Y, Perreault S..  (2018)  Atropisomerism by Design: Discovery of a Selective and Stable Phosphoinositide 3-Kinase (PI3K) β Inhibitor.,  61  (15): [PMID:30015489] [10.1021/acs.jmedchem.8b00797]

2. Chandrasekhar J, Dick R, Van Veldhuizen J, Koditek D, Lepist EI, McGrath ME, Patel L, Phillips G, Sedillo K, Somoza JR, Therrien J, Till NA, Treiberg J, Villaseñor AG, Zherebina Y, Perreault S..  (2018)  Atropisomerism by Design: Discovery of a Selective and Stable Phosphoinositide 3-Kinase (PI3K) β Inhibitor.,  61  (15): [PMID:30015489] [10.1021/acs.jmedchem.8b00797]

3. Chandrasekhar J, Dick R, Van Veldhuizen J, Koditek D, Lepist EI, McGrath ME, Patel L, Phillips G, Sedillo K, Somoza JR, Therrien J, Till NA, Treiberg J, Villaseñor AG, Zherebina Y, Perreault S..  (2018)  Atropisomerism by Design: Discovery of a Selective and Stable Phosphoinositide 3-Kinase (PI3K) β Inhibitor.,  61  (15): [PMID:30015489] [10.1021/acs.jmedchem.8b00797]

4. Perreault S, Arjmand F, Chandrasekhar J, Hao J, Keegan KS, Koditek D, Lepist EI, Matson CK, McGrath ME, Patel L, Sedillo K, Therrien J, Till NA, Tomkinson A, Treiberg J, Zherebina Y, Phillips G..  (2020)  Discovery of an Atropisomeric PI3Kβ Selective Inhibitor through Optimization of the Hinge Binding Motif.,  11  (6): [PMID:32551006] [10.1021/acsmedchemlett.0c00095]

5. Perreault S, Arjmand F, Chandrasekhar J, Hao J, Keegan KS, Koditek D, Lepist EI, Matson CK, McGrath ME, Patel L, Sedillo K, Therrien J, Till NA, Tomkinson A, Treiberg J, Zherebina Y, Phillips G..  (2020)  Discovery of an Atropisomeric PI3Kβ Selective Inhibitor through Optimization of the Hinge Binding Motif.,  11  (6): [PMID:32551006] [10.1021/acsmedchemlett.0c00095]

6. Perreault S, Arjmand F, Chandrasekhar J, Hao J, Keegan KS, Koditek D, Lepist EI, Matson CK, McGrath ME, Patel L, Sedillo K, Therrien J, Till NA, Tomkinson A, Treiberg J, Zherebina Y, Phillips G..  (2020)  Discovery of an Atropisomeric PI3Kβ Selective Inhibitor through Optimization of the Hinge Binding Motif.,  11  (6): [PMID:32551006] [10.1021/acsmedchemlett.0c00095]

Source

Source(1):

• Scientific Literature