Rac-N-(4-Amino-6-methylene-5-(4-phenoxyphenyl)-7,8-dihydro-6Hpyrimido[5,4-b]pyrrolizin-7-yl)acrylamide

ID: ALA4217006

PubChem CID: 139507347

Max Phase: Preclinical

Molecular Formula: C25H21N5O2

Molecular Weight: 423.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)NC1Cn2c(c(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1=C

Standard InChI:  InChI=1S/C25H21N5O2/c1-3-20(31)29-19-13-30-23(15(19)2)21(22-24(26)27-14-28-25(22)30)16-9-11-18(12-10-16)32-17-7-5-4-6-8-17/h3-12,14,19H,1-2,13H2,(H,29,31)(H2,26,27,28)

Standard InChI Key:  KJRVCMVPIKELBC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   15.8203  -20.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5513  -21.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2480  -20.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1477  -21.1007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7427  -19.8015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6890  -18.9246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1971  -19.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4152  -19.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4240  -18.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2112  -18.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7036  -17.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4851  -17.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4764  -18.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9052  -18.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1864  -19.0981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2039  -17.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9139  -17.8682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3209  -16.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4966  -16.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1138  -16.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5554  -15.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3797  -15.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7624  -16.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1727  -14.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6143  -13.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2317  -13.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6732  -12.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4975  -12.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8802  -13.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4386  -14.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7617  -18.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2127  -16.6233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
  6 13  1  0
 14 15  1  0
 16 17  1  0
 14 17  2  0
 12 16  2  0
 13 15  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 25 30  2  0
 24 25  1  0
 21 24  1  0
 11 18  1  0
  9 31  2  0
 16 32  1  0
  5  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217006

   ---

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: 423.48

Molecular Weight (Monoisotopic): 423.1695

AlogP: 4.17

#Rotatable Bonds: 5

Polar Surface Area: 95.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.41

CX LogP: 3.68

CX LogD: 3.64

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.47

Np Likeness Score: -0.09

References

1. Xue Y, Song P, Song Z, Wang A, Tong L, Geng M, Ding J, Liu Q, Sun L, Xie H, Zhang A..  (2018)  Discovery of 4,7-Diamino-5-(4-phenoxyphenyl)-6-methylene-pyrimido[5,4- b]pyrrolizines as Novel Bruton's Tyrosine Kinase Inhibitors.,  61  (10): [PMID:29715023] [10.1021/acs.jmedchem.8b00441]

Source

Source(1):

• Scientific Literature