3-(1,3-Benzodioxol-5-yl)-N-(4-pyridylmethyl)pyrazolo[1,5-a]pyrimidin-5-amine

ID: ALA4547553

PubChem CID: 24866033

Max Phase: Preclinical

Molecular Formula: C19H15N5O2

Molecular Weight: 345.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1cc(CNc2ccn3ncc(-c4ccc5c(c4)OCO5)c3n2)ccn1

Standard InChI:  InChI=1S/C19H15N5O2/c1-2-16-17(26-12-25-16)9-14(1)15-11-22-24-8-5-18(23-19(15)24)21-10-13-3-6-20-7-4-13/h1-9,11H,10,12H2,(H,21,23)

Standard InChI Key:  DJMJVMXMRFYVLC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.7193   -4.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4273   -5.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4255   -3.7183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1341   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1344   -4.9422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9131   -5.1950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3941   -4.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9126   -3.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1633   -3.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9639   -2.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8661   -1.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6175   -2.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0126   -3.7188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3050   -4.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5972   -3.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6006   -2.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8936   -2.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1851   -2.9018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1879   -3.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8954   -4.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6690   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2166   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9598   -1.8104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8716   -1.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0739   -0.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
 10 11  2  0
 11 23  1  0
 22 12  1  0
 12 13  2  0
 13 10  1  0
  9 10  1  0
  1 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547553

   3-(1,3-benzodioxol-5-yl)-N-(pyridin-4-ylmethyl)pyrazolo[1,5-a]pyrimidin-5-amine

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: 345.36

Molecular Weight (Monoisotopic): 345.1226

AlogP: 3.13

#Rotatable Bonds: 4

Polar Surface Area: 73.57

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.02

CX LogP: 2.50

CX LogD: 2.50

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.61

Np Likeness Score: -1.23

References

1. Newton R, Waszkowycz B, Seewooruthun C, Burschowsky D, Richards M, Hitchin S, Begum H, Watson A, French E, Hamilton N, Jones S, Lin LY, Waddell I, Echalier A, Bayliss R, Jordan AM, Ogilvie D..  (2020)  Discovery and Optimization of wt-RET/KDR-Selective Inhibitors of RETV804M Kinase.,  11  (4): [PMID:32292556] [10.1021/acsmedchemlett.9b00615]

Source

Source(1):

• Scientific Literature