(R)-1-(3-(3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-(1-phenylethyl)urea

ID: ALA2089213

PubChem CID: 70691266

Max Phase: Preclinical

Molecular Formula: C20H20N8O

Molecular Weight: 388.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)Nc1cccc(Nc2ncc3c(N)n[nH]c3n2)c1)c1ccccc1

Standard InChI:  InChI=1S/C20H20N8O/c1-12(13-6-3-2-4-7-13)23-20(29)25-15-9-5-8-14(10-15)24-19-22-11-16-17(21)27-28-18(16)26-19/h2-12H,1H3,(H2,23,25,29)(H4,21,22,24,26,27,28)/t12-/m1/s1

Standard InChI Key:  BUVVCBTZYXTSHY-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

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   18.9016   -6.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6164   -7.4027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6146   -5.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3300   -6.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3348   -6.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1223   -7.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6042   -6.5646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1145   -5.8989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3648   -5.1128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1868   -7.4018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1861   -8.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4712   -8.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4702   -9.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1849   -9.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9021   -9.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8995   -8.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6177   -9.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3310   -9.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0466   -9.8655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3287   -8.6300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7599   -9.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4755   -9.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7577   -8.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4745  -10.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1892  -11.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9036  -10.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8986   -9.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1833   -9.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
 16 18  1  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 19 21  2  0
  9 10  1  0
 20 22  1  0
  5  6  1  0
 22 23  1  6
  2 11  1  0
 22 24  1  0
 23 25  2  0
 11 12  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 12 13  2  0
 27 28  1  0
  3  6  2  0
 28 29  2  0
 29 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2089213

   1-[3-[(3-amino-2H-pyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-[(1R)-1-phenylethyl]urea

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: 388.44

Molecular Weight (Monoisotopic): 388.1760

AlogP: 3.56

#Rotatable Bonds: 5

Polar Surface Area: 133.64

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.16

CX Basic pKa: 3.43

CX LogP: 2.89

CX LogD: 2.89

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -1.67

References

1. Yang LL, Li GB, Yan HX, Sun QZ, Ma S, Ji P, Wang ZR, Feng S, Zou J, Yang SY..  (2012)  Discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization.,  56  [PMID:22944772] [10.1016/j.ejmech.2012.08.007]

Source

Source(1):

• Scientific Literature