4'-(piperazin-1-yl)-1,3,6',7'-tetrahydro-5'H-spiro[indene-2,8'-quinazolin]-2'-amine

ID: ALA1078020

PubChem CID: 46882022

Max Phase: Preclinical

Molecular Formula: C20H25N5

Molecular Weight: 335.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CCNCC2)c2c(n1)C1(CCC2)Cc2ccccc2C1

Standard InChI:  InChI=1S/C20H25N5/c21-19-23-17-16(18(24-19)25-10-8-22-9-11-25)6-3-7-20(17)12-14-4-1-2-5-15(14)13-20/h1-2,4-5,22H,3,6-13H2,(H2,21,23,24)

Standard InChI Key:  UIDKYXICKBNCIW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   -2.8881  -26.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1046  -25.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5818  -26.5763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1766  -24.8887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7464  -25.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497  -24.8844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4651  -24.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680  -23.6509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313  -26.1256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4658  -26.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1773  -25.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8929  -26.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1812  -27.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646  -26.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2272  -26.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9304  -25.2851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498  -24.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2660  -24.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5602  -25.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0389  -26.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338  -26.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774  -27.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932  -26.9495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934  -26.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778  -25.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 16  1  0
  5  6  1  0
 10 14  1  0
 11  1  1  0
  1 12  1  0
 12 13  1  0
 13 14  1  0
 15  3  1  0
  6  7  2  0
 15 16  2  0
  7  4  1  0
 16 17  1  0
  3  1  1  0
 17 18  2  0
  7  8  1  0
 18 19  1  0
  1  2  1  0
 19 20  2  0
 20 15  1  0
  9 21  1  0
  5  9  1  0
 10 11  1  0
  4 11  2  0
 10  5  2  0
  9 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078020

   4'-piperazin-1-ylspiro[1,3-dihydroindene-2,8'-6,7-dihydro-5H-quinazoline]-2'-amine

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: 335.46

Molecular Weight (Monoisotopic): 335.2110

AlogP: 1.84

#Rotatable Bonds: 1

Polar Surface Area: 67.07

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 3.67

CX LogD: 2.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.40

References

1. Koenig JR, Liu H, Drizin I, Witte DG, Carr TL, Manelli AM, Milicic I, Strakhova MI, Miller TR, Esbenshade TA, Brioni JD, Cowart M..  (2010)  Rigidified 2-aminopyrimidines as histamine H4 receptor antagonists: effects of substitution about the rigidifying ring.,  20  (6): [PMID:20171098] [10.1016/j.bmcl.2010.01.131]

Source

Source(1):

• Scientific Literature