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

ID: ALA4643981

PubChem CID: 134372827

Max Phase: Preclinical

Molecular Formula: C24H14ClF2N7

Molecular Weight: 473.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nc2c(-c3nnc[nH]3)cc(-c3ccnc(Cl)c3)cc2n1-c1ccnc2c(F)ccc(F)c12

Standard InChI:  InChI=1S/C24H14ClF2N7/c1-12-32-22-15(24-30-11-31-33-24)8-14(13-4-6-28-20(25)10-13)9-19(22)34(12)18-5-7-29-23-17(27)3-2-16(26)21(18)23/h2-11H,1H3,(H,30,31,33)

Standard InChI Key:  QCSBWICWLKTERT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   11.4035   -3.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4024   -4.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1182   -4.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1164   -2.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8329   -3.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8337   -4.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5499   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2660   -4.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2613   -3.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5444   -2.9030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1139   -2.0824    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.1201   -5.3878    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5513   -5.3774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8835   -5.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1432   -6.6506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2209   -5.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9665   -6.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.3218   -7.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5775   -6.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0234   -5.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2637   -8.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4785   -8.3012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4786   -9.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2641   -9.3803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7509   -8.7115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0604   -5.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3803   -6.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9286   -6.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7307   -6.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9817   -5.7745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4246   -5.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6245   -5.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2828   -7.1659    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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  6  7  1  0
  7  8  2  0
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  3 12  1  0
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  7 13  1  0
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 20 21  2  0
 21 16  1  0
 22 23  1  0
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 24 25  2  0
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 26 22  2  0
 18 22  1  0
 14 27  1  0
 20 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 30 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4643981

   ---

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: 473.87

Molecular Weight (Monoisotopic): 473.0967

AlogP: 5.66

#Rotatable Bonds: 3

Polar Surface Area: 85.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.53

CX Basic pKa: 4.70

CX LogP: 3.91

CX LogD: 3.90

Aromatic Rings: 6

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: -1.10

References

1. 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