1-(azetidin-3-ylmethyl)-3-(6-ethoxynaphthalen-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

ID: ALA4587540

PubChem CID: 155566556

Max Phase: Preclinical

Molecular Formula: C21H22N6O

Molecular Weight: 374.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccc2cc(-c3nn(CC4CNC4)c4ncnc(N)c34)ccc2c1

Standard InChI:  InChI=1S/C21H22N6O/c1-2-28-17-6-5-14-7-16(4-3-15(14)8-17)19-18-20(22)24-12-25-21(18)27(26-19)11-13-9-23-10-13/h3-8,12-13,23H,2,9-11H2,1H3,(H2,22,24,25)

Standard InChI Key:  JGBKZDBBHGWUNI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.9291  -10.0422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9216  -10.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6248  -11.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6173  -12.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950  -12.3609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6427  -13.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4312  -13.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1460  -12.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5486  -13.6742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8338  -14.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8846  -11.7045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4097  -11.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6713  -10.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1281   -9.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3855   -8.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1904   -8.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4520   -7.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2528   -7.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5144   -6.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3193   -6.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5395   -6.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8002   -8.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5386   -9.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7337   -9.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4721  -10.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9066  -12.5019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1992  -12.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2068  -11.2661    0.0000 N   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  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  7 10  1  0
  5 11  1  0
 11 12  2  0
  3 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  2  0
 16 24  1  0
 23 24  1  0
 24 25  2  0
 13 25  1  0
  4 26  2  0
 26 27  1  0
 27 28  2  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4587540

   ---

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: 374.45

Molecular Weight (Monoisotopic): 374.1855

AlogP: 2.85

#Rotatable Bonds: 5

Polar Surface Area: 90.88

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.43

CX LogP: 2.37

CX LogD: -0.45

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.93

References

1. Vidadala RS, Rivas KL, Ojo KK, Hulverson MA, Zambriski JA, Bruzual I, Schultz TL, Huang W, Zhang Z, Scheele S, DeRocher AE, Choi R, Barrett LK, Siddaramaiah LK, Hol WG, Fan E, Merritt EA, Parsons M, Freiberg G, Marsh K, Kempf DJ, Carruthers VB, Isoherranen N, Doggett JS, Van Voorhis WC, Maly DJ..  (2016)  Development of an Orally Available and Central Nervous System (CNS) Penetrant Toxoplasma gondii Calcium-Dependent Protein Kinase 1 (TgCDPK1) Inhibitor with Minimal Human Ether-a-go-go-Related Gene (hERG) Activity for the Treatment of Toxoplasmosis.,  59  (13): [PMID:27309760] [10.1021/acs.jmedchem.6b00760]

Source

Source(1):

• Scientific Literature