1-(2-Chloro-7-((3S,5S)-3,5-dimethylmorpholino)pyrazolo[1,5-a]pyrimidin-6-yl)-3-(2-(trifluoromethyl)pyridin-4-yl)urea

ID: ALA4796225

PubChem CID: 146680905

Max Phase: Preclinical

Molecular Formula: C19H19ClF3N7O2

Molecular Weight: 469.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1COC[C@H](C)N1c1c(NC(=O)Nc2ccnc(C(F)(F)F)c2)cnc2cc(Cl)nn12

Standard InChI:  InChI=1S/C19H19ClF3N7O2/c1-10-8-32-9-11(2)29(10)17-13(7-25-16-6-15(20)28-30(16)17)27-18(31)26-12-3-4-24-14(5-12)19(21,22)23/h3-7,10-11H,8-9H2,1-2H3,(H2,24,26,27,31)/t10-,11-/m0/s1

Standard InChI Key:  BFPCFGGFGQMJQG-QWRGUYRKSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.4970   -4.8701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -4.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -3.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4970   -3.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -4.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -3.6439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0103   -3.3899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5272   -4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -4.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9112   -3.2419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6177   -3.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266   -3.2461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6153   -4.4698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7100   -4.0547    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0331   -3.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0293   -4.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7350   -4.8856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4449   -4.4790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4447   -3.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7384   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1521   -3.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8601   -3.6567    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.1517   -2.4314    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8575   -2.8354    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4989   -2.4186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2119   -2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2158   -1.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5109   -0.7804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8004   -1.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7948   -2.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9184   -2.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844   -2.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
  8 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  4 25  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 26 31  1  6
 30 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4796225

   ---

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: 469.86

Molecular Weight (Monoisotopic): 469.1241

AlogP: 4.05

#Rotatable Bonds: 3

Polar Surface Area: 96.68

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.74

CX Basic pKa: 1.87

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -1.59

References

1. Pissot Soldermann C,Simic O,Renatus M,Erbel P,Melkko S,Wartmann M,Bigaud M,Weiss A,McSheehy P,Endres R,Santos P,Blank J,Schuffenhauer A,Bold G,Buschmann N,Zoller T,Altmann E,Manley PW,Dix I,Buchdunger E,Scesa J,Quancard J,Schlapbach A,Bornancin F,Radimerski T,Régnier CH.  (2020)  Discovery of Potent, Highly Selective, and In Vivo Efficacious, Allosteric MALT1 Inhibitors by Iterative Scaffold Morphing.,  63  (23): [PMID:33252239] [10.1021/acs.jmedchem.0c01245]

2. Quancard J,Simic O,Pissot Soldermann C,Aichholz R,Blatter M,Renatus M,Erbel P,Melkko S,Endres R,Sorge M,Kieffer L,Wagner T,Beltz K,Mcsheehy P,Wartmann M,Régnier CH,Calzascia T,Radimerski T,Bigaud M,Weiss A,Bornancin F,Schlapbach A.  (2020)  Optimization of the In Vivo Potency of Pyrazolopyrimidine MALT1 Protease Inhibitors by Reducing Metabolism and Increasing Potency in Whole Blood.,  63  (23): [PMID:33216547] [10.1021/acs.jmedchem.0c01246]

Source

Source(1):

• Scientific Literature