2-(tert-butylamino)-8-((R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-3-(((S)-4-methylmorpholin-2-yl)methyl)quinazolin-4(3H)-one

ID: ALA4476513

PubChem CID: 155538459

Max Phase: Preclinical

Molecular Formula: C25H32N6O3

Molecular Weight: 464.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1NC(=O)c2cc(-c3cccc4c(=O)n(C[C@@H]5CN(C)CCO5)c(NC(C)(C)C)nc34)[nH]c21

Standard InChI:  InChI=1S/C25H32N6O3/c1-14-20-18(22(32)26-14)11-19(27-20)16-7-6-8-17-21(16)28-24(29-25(2,3)4)31(23(17)33)13-15-12-30(5)9-10-34-15/h6-8,11,14-15,27H,9-10,12-13H2,1-5H3,(H,26,32)(H,28,29)/t14-,15+/m1/s1

Standard InChI Key:  BZUBDLKATGBRRF-CABCVRRESA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   15.8527   -9.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8527  -10.5244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5580  -10.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2632  -10.5244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5580   -9.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2609   -9.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9681   -9.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9735   -8.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2659   -8.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5617   -8.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6766   -9.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7566  -10.5302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4253   -9.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9681  -10.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5582  -10.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1038  -11.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8511  -10.9848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7671  -10.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9323  -12.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3755   -9.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1438   -9.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5580  -11.7461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2657  -12.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2657  -12.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9734  -11.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9700  -12.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1456  -10.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4373  -10.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4383   -9.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7341   -9.2986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0245   -9.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0238  -10.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7325  -10.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7360   -8.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
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 12 15  1  0
 14 13  1  0
 13 11  2  0
  7 11  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 16 19  1  6
 18 20  2  0
  1 21  2  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  2 27  1  0
 28 27  1  1
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 30 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476513

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 464.57

Molecular Weight (Monoisotopic): 464.2536

AlogP: 2.74

#Rotatable Bonds: 4

Polar Surface Area: 104.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.98

CX Basic pKa: 6.54

CX LogP: 1.72

CX LogD: 1.66

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: -0.54

References

1. Wang HL, Andrews KL, Booker SK, Canon J, Cee VJ, Chavez F, Chen Y, Eastwood H, Guerrero N, Herberich B, Hickman D, Lanman BA, Laszlo J, Lee MR, Lipford JR, Mattson B, Mohr C, Nguyen Y, Norman MH, Pettus LH, Powers D, Reed AB, Rex K, Sastri C, Tamayo N, Wang P, Winston JT, Wu B, Wu Q, Wu T, Wurz RP, Xu Y, Zhou Y, Tasker AS..  (2019)  Discovery of ( R)-8-(6-Methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4- b]pyrrol-2-yl)-3-(1-methylcyclopropyl)-2-((1-methylcyclopropyl)amino)quinazolin-4(3 H)-one, a Potent and Selective Pim-1/2 Kinase Inhibitor for Hematological Malignancies.,  62  (3): [PMID:30624936] [10.1021/acs.jmedchem.8b01733]

Source

Source(1):

• Scientific Literature