(E)-N-[7-hydroxy-4-(3-methyl-4-pyrazolo[1,5-a]pyrimidin-6-yloxy-anilino)quinazolin-6-yl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide

ID: ALA5190132

PubChem CID: 168283966

Max Phase: Preclinical

Molecular Formula: C29H28N8O3

Molecular Weight: 536.60

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2ncnc3cc(O)c(NC(=O)/C=C/[C@H]4CCCN4C)cc23)ccc1Oc1cnc2ccnn2c1

Standard InChI:  InChI=1S/C29H28N8O3/c1-18-12-19(5-7-26(18)40-21-15-30-27-9-10-33-37(27)16-21)34-29-22-13-24(25(38)14-23(22)31-17-32-29)35-28(39)8-6-20-4-3-11-36(20)2/h5-10,12-17,20,38H,3-4,11H2,1-2H3,(H,35,39)(H,31,32,34)/b8-6+/t20-/m1/s1

Standard InChI Key:  HGURWXVQNCHCIP-CPSHHHPTSA-N

Molfile:  

 
     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   -1.4374   -1.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -1.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -2.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7210   -2.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166   -1.2357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -2.4734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    0.0019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4163    0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4165    1.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294    1.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8442    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340    0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294    2.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5589    1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    1.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7028    1.2376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7028    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881   -0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1597   -0.8071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3160   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9803   -0.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1521   -0.8219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -1.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5813   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -2.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2960   -1.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1521   -2.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0106   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0968   -0.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9036    0.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3160   -0.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640   -1.1574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9776   -1.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  3  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  4 10  1  0
  7 11  1  0
 11 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
 14 18  1  0
 15 19  1  0
 19 20  1  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  1  0
 25 24  1  0
 20 25  2  0
 24 26  1  0
 23 27  2  0
 27 28  1  0
 28 26  2  0
  1 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 31 33  2  0
  6 34  1  0
 35 33  1  6
 36 35  1  0
 37 36  1  0
 38 37  1  0
 38 39  1  0
 39 35  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5190132

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 536.60

Molecular Weight (Monoisotopic): 536.2284

AlogP: 4.81

#Rotatable Bonds: 7

Polar Surface Area: 129.80

Molecular Species: BASE

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.77

CX Basic pKa: 8.75

CX LogP: 2.83

CX LogD: 2.80

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.20

Np Likeness Score: -0.92

References

1. Li D, Tu Y, Jin K, Duan L, Hong Y, Xu J, Chen N, Zhang Z, Zuo H, Gong W, Zhang J, Wang Q, Qian H, Wang X, Ke Y, Xia G..  (2022)  Discovery of SPH5030, a Selective, Potent, and Irreversible Tyrosine Kinase Inhibitor for HER2-Amplified and HER2-Mutant Cancer Treatment.,  65  (7.0): [PMID:35319895] [10.1021/acs.jmedchem.1c00710]

Source

Source(1):

• Scientific Literature