(S)-8-Chloro-2-(1-((2,6-diamino-5-chloropyrimidin-4-yl)-amino)ethyl)-6-fluoro-3-(1H-pyrazol-3-yl)quinazolin-4(3H)-one

ID: ALA4082978

Cas Number: 1842380-77-1

PubChem CID: 118575663

Max Phase: Preclinical

Molecular Formula: C17H14Cl2FN9O

Molecular Weight: 450.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Nc1nc(N)nc(N)c1Cl)c1nc2c(Cl)cc(F)cc2c(=O)n1-c1cc[nH]n1

Standard InChI:  InChI=1S/C17H14Cl2FN9O/c1-6(24-14-11(19)13(21)26-17(22)27-14)15-25-12-8(4-7(20)5-9(12)18)16(30)29(15)10-2-3-23-28-10/h2-6H,1H3,(H,23,28)(H5,21,22,24,26,27)/t6-/m0/s1

Standard InChI Key:  SAWISWWSHNTVLW-LURJTMIESA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   22.6406  -10.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6394  -11.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3475  -12.0212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3457  -10.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0543  -10.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0531  -11.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7632  -12.0256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4790  -11.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4802  -10.7911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7656  -10.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7656   -9.5580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1856  -12.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1833  -12.8441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8944  -11.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8898  -13.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2994  -14.0746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2991  -13.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5928  -12.8464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5896  -14.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8863  -14.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1872  -10.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5874  -15.2985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9270  -10.7166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4744  -10.1136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0701   -9.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2728   -9.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1774  -14.4799    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.0065  -12.8441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3472  -12.8384    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.9328  -10.3842    0.0000 F   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
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  6
 12 14  1  0
 13 15  1  0
 15 20  2  0
 19 16  2  0
 16 17  1  0
 17 18  2  0
 18 15  1  0
 19 20  1  0
  9 21  1  0
 19 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 20 27  1  0
 17 28  1  0
  3 29  1  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4082978

   PI3K-IN-6

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: 450.26

Molecular Weight (Monoisotopic): 449.0682

AlogP: 2.68

#Rotatable Bonds: 4

Polar Surface Area: 153.42

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.14

CX Basic pKa: 6.16

CX LogP: 2.91

CX LogD: 2.90

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -1.52

References

1. Perreault S, Chandrasekhar J, Cui ZH, Evarts J, Hao J, Kaplan JA, Kashishian A, Keegan KS, Kenney T, Koditek D, Lad L, Lepist EI, McGrath ME, Patel L, Phillips B, Therrien J, Treiberg J, Yahiaoui A, Phillips G..  (2017)  Discovery of a Phosphoinositide 3-Kinase (PI3K) β/δ Inhibitor for the Treatment of Phosphatase and Tensin Homolog (PTEN) Deficient Tumors: Building PI3Kβ Potency in a PI3Kδ-Selective Template by Targeting Nonconserved Asp856.,  60  (4): [PMID:28106991] [10.1021/acs.jmedchem.6b01821]

Source

Source(1):

• Scientific Literature