5-(2-Guanidino-1-ethyl)thio-3-isopropyl-7-[4-(2-pyridyl)-benzyl]amino-1H-pyrazolo[4,3-d]pyrimidine

ID: ALA4524174

PubChem CID: 155520153

Max Phase: Preclinical

Molecular Formula: C23H27N9S

Molecular Weight: 461.60

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1n[nH]c2c(NCc3ccc(-c4ccccn4)cc3)nc(SCCNC(=N)N)nc12

Standard InChI:  InChI=1S/C23H27N9S/c1-14(2)18-19-20(32-31-18)21(30-23(29-19)33-12-11-27-22(24)25)28-13-15-6-8-16(9-7-15)17-5-3-4-10-26-17/h3-10,14H,11-13H2,1-2H3,(H,31,32)(H4,24,25,27)(H,28,29,30)

Standard InChI Key:  RSVQGELPHGKSOU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   31.1050   -4.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9290   -4.2525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3402   -3.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9286   -2.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1014   -2.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6940   -3.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1622   -3.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5744   -4.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3994   -4.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8133   -3.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3961   -2.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5725   -2.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6391   -3.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0527   -4.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8785   -4.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2878   -4.9680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1128   -4.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5258   -4.2513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2839   -3.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1032   -3.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3551   -2.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6916   -2.2770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.0297   -2.7596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.1401   -2.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7546   -3.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3106   -1.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5261   -5.6823    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.1137   -6.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2879   -6.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8754   -7.1137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0496   -7.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6371   -7.8296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6363   -6.3993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 20  1  0
 19 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4524174

   ---

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: 461.60

Molecular Weight (Monoisotopic): 461.2110

AlogP: 3.73

#Rotatable Bonds: 9

Polar Surface Area: 141.28

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.51

CX Basic pKa: 11.83

CX LogP: 2.72

CX LogD: 1.26

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.08

Np Likeness Score: -1.32

References

1. Jorda R, Havlíček L, Šturc A, Tušková D, Daumová L, Alam M, Škerlová J, Nekardová M, Peřina M, Pospíšil T, Široká J, Urbánek L, Pachl P, Řezáčová P, Strnad M, Klener P, Kryštof V..  (2019)  3,5,7-Substituted Pyrazolo[4,3- d]pyrimidine Inhibitors of Cyclin-Dependent Kinases and Their Evaluation in Lymphoma Models.,  62  (9): [PMID:30943029] [10.1021/acs.jmedchem.9b00189]

Source

Source(1):

• Scientific Literature