5-(5-((hexyl(methyl)amino)methyl)thiophen-3-yl)-6-isopropyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

ID: ALA4556977

PubChem CID: 155556847

Max Phase: Preclinical

Molecular Formula: C22H29N5OS

Molecular Weight: 411.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCN(C)Cc1cc(-c2[nH]c3c(C#N)cnn3c(=O)c2C(C)C)cs1

Standard InChI:  InChI=1S/C22H29N5OS/c1-5-6-7-8-9-26(4)13-18-10-16(14-29-18)20-19(15(2)3)22(28)27-21(25-20)17(11-23)12-24-27/h10,12,14-15,25H,5-9,13H2,1-4H3

Standard InChI Key:  MSRPYQLIKRKXDL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   18.6012  -15.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3432  -16.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0119  -16.7967    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.6806  -16.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1750  -15.5243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8881  -15.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8881  -14.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1750  -13.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4618  -15.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4573  -14.2880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6707  -14.0385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1873  -14.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6780  -15.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6048  -13.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3150  -14.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6072  -13.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1761  -13.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4333  -16.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1797  -16.9424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3906  -16.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1070  -16.3140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8217  -16.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1086  -15.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5339  -16.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2486  -16.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9650  -16.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6797  -16.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3960  -16.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
 11  9  1  0
 10  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  2  0
  7  2  1  0
 19 20  3  0
 14 19  1  0
  5 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556977

   ---

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: 411.58

Molecular Weight (Monoisotopic): 411.2093

AlogP: 4.76

#Rotatable Bonds: 9

Polar Surface Area: 77.19

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.54

CX Basic pKa: 8.79

CX LogP: 4.32

CX LogD: 3.04

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -1.31

References

1. Miyake Y, Itoh Y, Hatanaka A, Suzuma Y, Suzuki M, Kodama H, Arai Y, Suzuki T..  (2019)  Identification of novel lysine demethylase 5-selective inhibitors by inhibitor-based fragment merging strategy.,  27  (6): [PMID:30745098] [10.1016/j.bmc.2019.02.006]

Source

Source(1):

• Scientific Literature