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

ID: ALA4211949

PubChem CID: 145967187

Max Phase: Preclinical

Molecular Formula: C25H21N5O2

Molecular Weight: 423.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)N[C@@H]1Cn2c(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)/t19-/m1/s1

Standard InChI Key:  KJRVCMVPIKELBC-LJQANCHMSA-N

Molfile:  

     RDKit          2D

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   16.2323  -23.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1058  -23.4423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4503  -20.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6862  -18.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0624  -17.1090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4762  -16.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0729  -15.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4868  -14.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3040  -14.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7073  -15.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7730  -20.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1258  -18.9281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 11 18  1  0
  9 31  2  0
 16 32  1  0
  8  5  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4211949

   ---

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