1-(6-Oxo-1,2,3,4,6,10b-hexahydropyrido[2,1-a]isoindol-10-yl)-3-(pyrazin-2-yl)urea

ID: ALA2180863

PubChem CID: 67283829

Max Phase: Preclinical

Molecular Formula: C17H17N5O2

Molecular Weight: 323.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cnccn1)Nc1cccc2c1C1CCCCN1C2=O

Standard InChI:  InChI=1S/C17H17N5O2/c23-16-11-4-3-5-12(15(11)13-6-1-2-9-22(13)16)20-17(24)21-14-10-18-7-8-19-14/h3-5,7-8,10,13H,1-2,6,9H2,(H2,19,20,21,24)

Standard InChI Key:  KIHCZOJSOYPCCE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    7.6251   -7.3642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8001   -7.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3876   -6.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3876   -8.0787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5626   -8.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501   -7.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501   -8.7932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251   -7.3642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125   -8.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251   -8.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4146   -7.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1683   -6.9273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0820   -6.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2751   -5.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8626   -5.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0376   -5.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6251   -5.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0376   -6.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8626   -6.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3283   -8.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9958   -8.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7495   -8.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8357   -7.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6951   -5.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  6  1  0
  5  7  2  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  7 10  1  0
  4  5  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 11 19  1  0
 14 19  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 11 20  1  0
 12 23  1  0
 13 24  2  0
  1 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2180863

   1-(6-oxo-2,3,4,10b-tetrahydro-1H-pyrido[2,1-a]isoindol-10-yl)-3-pyrazin-2-ylurea

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: 323.36

Molecular Weight (Monoisotopic): 323.1382

AlogP: 2.80

#Rotatable Bonds: 2

Polar Surface Area: 87.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.38

CX Basic pKa: 0.02

CX LogP: 1.24

CX LogD: 1.24

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: -1.12

References

1. Boulahjar R, Ouach A, Matteo C, Bourg S, Ravache M, le Guével R, Marionneau S, Oullier T, Lozach O, Meijer L, Guguen-Guillouzo C, Lazar S, Akssira M, Troin Y, Guillaumet G, Routier S..  (2012)  Novel tetrahydropyrido[1,2-a]isoindolone derivatives (valmerins): potent cyclin-dependent kinase/glycogen synthase kinase 3 inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts.,  55  (22): [PMID:23083119] [10.1021/jm3008536]

2. Ouach A, Boulahjar R, Vala C, Bourg S, Bonnet P, Guguen-Guillouzo C, Ravache M, Le Guevel R, Lozach O, Lazar S, Troin Y, Meijer L, Ruchaud S, Akssira M, Guillaumet G, Routier S..  (2016)  Novel optimization of valmerins (tetrahydropyrido[1,2-a]isoindolones) as potent dual CDK5/GSK3 inhibitors.,  115  [PMID:27019296] [10.1016/j.ejmech.2016.02.072]

Source

Source(1):

• Scientific Literature