3-(3-chlorophenoxy)-1-((1-methylpiperidin-4-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ID: ALA4090973

PubChem CID: 130431659

Max Phase: Preclinical

Molecular Formula: C18H21ClN6O

Molecular Weight: 372.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC(Cn2nc(Oc3cccc(Cl)c3)c3c(N)ncnc32)CC1

Standard InChI:  InChI=1S/C18H21ClN6O/c1-24-7-5-12(6-8-24)10-25-17-15(16(20)21-11-22-17)18(23-25)26-14-4-2-3-13(19)9-14/h2-4,9,11-12H,5-8,10H2,1H3,(H2,20,21,22)

Standard InChI Key:  OWAHNIJXSIARTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.2032   -6.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -4.9980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119   -5.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199   -6.2265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -4.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8267   -4.9944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315   -5.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6116   -6.0615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0889   -5.3964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6038   -4.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8686   -6.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157   -3.7720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518   -3.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501   -3.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971   -4.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9947   -4.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2434   -3.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6882   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8926   -3.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9334   -2.0496    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -7.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -7.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -7.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2642   -7.3362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0087   -6.5590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0639   -7.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  8 11  1  0
  5 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 11 21  1  0
 21 22  1  0
 21  1  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25  1  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090973

   ---

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: 372.86

Molecular Weight (Monoisotopic): 372.1465

AlogP: 3.20

#Rotatable Bonds: 4

Polar Surface Area: 82.09

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.19

CX LogP: 2.82

CX LogD: 1.03

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -1.32

References

1. Rutaganira FU, Barks J, Dhason MS, Wang Q, Lopez MS, Long S, Radke JB, Jones NG, Maddirala AR, Janetka JW, El Bakkouri M, Hui R, Shokat KM, Sibley LD..  (2017)  Inhibition of Calcium Dependent Protein Kinase 1 (CDPK1) by Pyrazolopyrimidine Analogs Decreases Establishment and Reoccurrence of Central Nervous System Disease by Toxoplasma gondii.,  60  (24): [PMID:28933846] [10.1021/acs.jmedchem.7b01192]

Source

Source(1):

• Scientific Literature