2-(1-((3S,5R)-3,5-dimethylpiperazin-1-yl)butyl)-3-ethyl-4-oxo-3,4-dihydroquinazoline-6-carbonitrile

ID: ALA4872266

PubChem CID: 153574224

Max Phase: Preclinical

Molecular Formula: C21H29N5O

Molecular Weight: 367.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCC(c1nc2ccc(C#N)cc2c(=O)n1CC)N1C[C@@H](C)N[C@@H](C)C1

Standard InChI:  InChI=1S/C21H29N5O/c1-5-7-19(25-12-14(3)23-15(4)13-25)20-24-18-9-8-16(11-22)10-17(18)21(27)26(20)6-2/h8-10,14-15,19,23H,5-7,12-13H2,1-4H3/t14-,15+,19?

Standard InChI Key:  UTDLBPRFVYDPAP-RTHVDDQRSA-N

Molfile:  

 
     RDKit          2D

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   18.1997  -26.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1985  -27.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9066  -28.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9048  -26.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6134  -26.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6122  -27.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3223  -28.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0381  -27.6341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0393  -26.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3247  -26.3930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3200  -28.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7480  -26.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4547  -26.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7447  -28.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7500  -25.5848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4663  -25.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4703  -24.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7654  -23.9528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0549  -24.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0492  -25.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1634  -26.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8702  -26.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1805  -23.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3496  -23.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4536  -27.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4947  -28.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7867  -28.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  7 11  2  0
  9 12  1  0
 12 13  1  0
  8 14  1  0
 12 15  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 17 23  1  1
 19 24  1  1
 14 25  1  0
 26 27  3  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872266

   ---

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: 367.50

Molecular Weight (Monoisotopic): 367.2372

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 73.95

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.39

CX LogP: 2.93

CX LogD: 0.96

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.88

Np Likeness Score: -1.03

References

1. Fernández A, Díaz JL, García M, Rodríguez-Escrich S, Lorente A, Enrech R, Dordal A, Portillo-Salido E, Porras M, Fernández B, Reinoso RF, Vela JM, Almansa C..  (2021)  Piperazinyl Bicyclic Derivatives as Selective Ligands of the α2δ-1 Subunit of Voltage-Gated Calcium Channels.,  12  (11.0): [PMID:34795870] [10.1021/acsmedchemlett.1c00416]

Source

Source(1):

• Scientific Literature