4-([1,4'-Bipiperidin]-1'-yl)-2-chloro-7-(4-fluorobenzyl)-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA4476179

PubChem CID: 155538173

Max Phase: Preclinical

Molecular Formula: C23H27ClFN5

Molecular Weight: 427.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Fc1ccc(Cn2ccc3c(N4CCC(N5CCCCC5)CC4)nc(Cl)nc32)cc1

Standard InChI:  InChI=1S/C23H27ClFN5/c24-23-26-21(29-13-8-19(9-14-29)28-11-2-1-3-12-28)20-10-15-30(22(20)27-23)16-17-4-6-18(25)7-5-17/h4-7,10,15,19H,1-3,8-9,11-14,16H2

Standard InChI Key:  QIHGFSRFUIRMKU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.9724  -15.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9724  -14.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2671  -13.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2674  -16.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5579  -16.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.2618  -17.9942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   20.5506  -19.2142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5472  -20.0306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2539  -20.4427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9654  -19.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9687  -20.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7489  -20.2865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2277  -19.6218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7435  -18.9611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0045  -21.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8045  -21.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0582  -22.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8574  -22.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4027  -21.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1432  -20.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3446  -20.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2029  -21.7268    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.8377  -20.4362    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 15 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476179

   ---

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: 427.95

Molecular Weight (Monoisotopic): 427.1939

AlogP: 4.73

#Rotatable Bonds: 4

Polar Surface Area: 37.19

Molecular Species: BASE

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.78

CX LogP: 5.10

CX LogD: 2.74

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: -1.42

References

1. Frank A, Meza-Arriagada F, Salas CO, Espinosa-Bustos C, Stark H..  (2019)  Nature-inspired pyrrolo[2,3-d]pyrimidines targeting the histamine H₃ receptor.,  27  (14): [PMID:31176569] [10.1016/j.bmc.2019.05.042]

Source

Source(1):

• Scientific Literature