5-Butyl-2-((4-chloro-2,6-difluorobenzyl)amino)-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

ID: ALA3617085

PubChem CID: 122190023

Max Phase: Preclinical

Molecular Formula: C18H16ClF2N5O

Molecular Weight: 391.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1cc(=O)n2nc(NCc3c(F)cc(Cl)cc3F)c(C#N)c2[nH]1

Standard InChI:  InChI=1S/C18H16ClF2N5O/c1-2-3-4-11-7-16(27)26-18(24-11)12(8-22)17(25-26)23-9-13-14(20)5-10(19)6-15(13)21/h5-7,24H,2-4,9H2,1H3,(H,23,25)

Standard InChI Key:  DJMVKKGOGVHJBN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -1.0028    1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9991   -2.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783    2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    3.7690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2216    1.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -1.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3513   -1.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161   -2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6160   -2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3512   -1.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5865    0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0866    0.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5511   -1.1985    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5280   -3.5826    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2559    0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4749    1.0936    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  4 10  2  0
  2 11  1  0
  9 12  1  0
 12 13  3  0
 11 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 19 25  1  0
 15 26  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3617085

   ---

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: 391.81

Molecular Weight (Monoisotopic): 391.1011

AlogP: 3.78

#Rotatable Bonds: 6

Polar Surface Area: 85.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.99

CX Basic pKa: ┄

CX LogP: 4.26

CX LogD: 4.26

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.53

References

1. Bertrand SM, Ancellin N, Beaufils B, Bingham RP, Borthwick JA, Boullay AB, Boursier E, Carter PS, Chung CW, Churcher I, Dodic N, Fouchet MH, Fournier C, Francis PL, Gummer LA, Herry K, Hobbs A, Hobbs CI, Homes P, Jamieson C, Nicodeme E, Pickett SD, Reid IH, Simpson GL, Sloan LA, Smith SE, Somers DO, Spitzfaden C, Suckling CJ, Valko K, Washio Y, Young RJ..  (2015)  The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits.,  58  (18): [PMID:26090771] [10.1021/acs.jmedchem.5b00313]

2. Bertrand, Sophie M SM and 31 more authors.  2015-09-24  The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits.  [PMID:26090771]

Source

Source(1):

• Scientific Literature