methyl 3-(4-(2-(3,5-difluoro-4-hydroxyphenylamino)-9H-purin-9-yl)phenyl)propanoate

ID: ALA4878141

PubChem CID: 164627102

Max Phase: Preclinical

Molecular Formula: C21H17F2N5O3

Molecular Weight: 425.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)CCc1ccc(-n2cnc3cnc(Nc4cc(F)c(O)c(F)c4)nc32)cc1

Standard InChI:  InChI=1S/C21H17F2N5O3/c1-31-18(29)7-4-12-2-5-14(6-3-12)28-11-25-17-10-24-21(27-20(17)28)26-13-8-15(22)19(30)16(23)9-13/h2-3,5-6,8-11,30H,4,7H2,1H3,(H,24,26,27)

Standard InChI Key:  DKBLAYGVRVTXEZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   21.2984  -21.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2972  -22.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0120  -22.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7284  -22.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7256  -21.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0102  -20.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0077  -20.0745    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.5838  -20.8999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5824  -22.5515    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.4436  -22.5505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1574  -22.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8691  -22.5487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.8615  -20.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1511  -21.3140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5785  -21.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5853  -22.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3835  -22.4021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8564  -21.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3640  -21.0413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6453  -23.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0973  -23.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3588  -24.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1681  -24.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7153  -24.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4509  -23.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4313  -25.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8858  -26.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1490  -26.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6034  -27.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9576  -27.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2208  -27.8744    0.0000 C   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
  6  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 16  1  0
 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 17 20  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878141

   ---

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: 425.40

Molecular Weight (Monoisotopic): 425.1299

AlogP: 3.65

#Rotatable Bonds: 6

Polar Surface Area: 102.16

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.28

CX Basic pKa: 1.09

CX LogP: 3.91

CX LogD: 3.86

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.36

Np Likeness Score: -0.94

References

1. Casalvieri KA, Matheson CJ, Warfield BM, Backos DS, Reigan P..  (2021)  N-Substituted pyrrolopyrimidines and purines as p90 ribosomal S6 protein kinase-2 (RSK2) inhibitors.,  41  [PMID:34034149] [10.1016/j.bmc.2021.116220]

Source

Source(1):

• Scientific Literature