(S)-4-amino-6-(1-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethylamino)-2-hydroxypyrimidine-5-carbonitrile

ID: ALA3805809

PubChem CID: 127050482

Max Phase: Preclinical

Molecular Formula: C21H16ClN7O2

Molecular Weight: 433.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Nc1nc(O)nc(N)c1C#N)c1nc2cccc(Cl)c2c(=O)n1-c1ccccc1

Standard InChI:  InChI=1S/C21H16ClN7O2/c1-11(25-18-13(10-23)17(24)27-21(31)28-18)19-26-15-9-5-8-14(22)16(15)20(30)29(19)12-6-3-2-4-7-12/h2-9,11H,1H3,(H4,24,25,27,28,31)/t11-/m0/s1

Standard InChI Key:  VMIIDRQAWRCLGX-NSHDSACASA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2093   -3.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5078   -3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9096    1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9075    2.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    0.7533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8008    3.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5044    3.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5096    1.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8113    0.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1077    1.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1025    3.0148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8166   -0.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8209   -1.9405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1490    0.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7966    4.9603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.6973    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  4 11  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  3 12  1  0
 18 19  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 23  1  0
 18 20  1  1
  2 18  1  0
 27 28  3  0
 24 27  1  0
 25 29  1  0
 21 30  1  0
  6 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3805809

   ---

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: 433.86

Molecular Weight (Monoisotopic): 433.1054

AlogP: 3.16

#Rotatable Bonds: 4

Polar Surface Area: 142.74

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: ┄

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -1.27

References

1. Patel L, Chandrasekhar J, Evarts J, Haran AC, Ip C, Kaplan JA, Kim M, Koditek D, Lad L, Lepist EI, McGrath ME, Novikov N, Perreault S, Puri KD, Somoza JR, Steiner BH, Stevens KL, Therrien J, Treiberg J, Villaseñor AG, Yeung A, Phillips G..  (2016)  2,4,6-Triaminopyrimidine as a Novel Hinge Binder in a Series of PI3Kδ Selective Inhibitors.,  59  (7): [PMID:26980109] [10.1021/acs.jmedchem.6b00213]

Source

Source(1):

• Scientific Literature