1-(4-(5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)ethanone

ID: ALA4214539

PubChem CID: 141404226

Max Phase: Preclinical

Molecular Formula: C18H17BrClN5O

Molecular Weight: 434.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Cl)cc1)N1CCN(c2ncnc3[nH]cc(Br)c23)CC1

Standard InChI:  InChI=1S/C18H17BrClN5O/c19-14-10-21-17-16(14)18(23-11-22-17)25-7-5-24(6-8-25)15(26)9-12-1-3-13(20)4-2-12/h1-4,10-11H,5-9H2,(H,21,22,23)

Standard InChI Key:  NCCGYJLNZVCYJX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   17.9520  -11.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2447  -11.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5350  -11.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6611  -11.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6603  -12.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3654  -13.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0824  -12.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0819  -11.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3697  -11.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2461  -12.6856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9558  -13.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9572  -13.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2449  -14.3238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5393  -13.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5379  -13.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9575  -16.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2451  -16.7791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5395  -16.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5381  -15.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2463  -15.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9560  -15.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7660  -16.6227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7656  -15.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2858  -15.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5105  -14.5230    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.7994  -13.1031    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  2  0
  1  4  1  0
  2  1  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 23 24  2  0
 22 24  1  0
 18 22  1  0
 19 23  1  0
 13 20  1  0
  2 10  1  0
 23 25  1  0
  7 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4214539

   ---

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: 434.72

Molecular Weight (Monoisotopic): 433.0305

AlogP: 3.27

#Rotatable Bonds: 3

Polar Surface Area: 65.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: 5.67

CX LogP: 3.50

CX LogD: 3.49

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.36

References

1. Liu Y, Yin Y, Zhang Z, Li CJ, Zhang H, Zhang D, Jiang C, Nomie K, Zhang L, Wang ML, Zhao G..  (2017)  Structural optimization elaborates novel potent Akt inhibitors with promising anticancer activity.,  138  [PMID:28704757] [10.1016/j.ejmech.2017.06.067]

2. Zhang D, Tong D, Yang D, Sun J, Zhang F, Zhao G..  (2018)  Design, synthesis and biological evaluation of AKT inhibitors bearing a piperidin-4-yl appendant.,  9  (8): [PMID:30151089] [10.1039/C8MD00197A]

Source

Source(1):

• Scientific Literature