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

ID: ALA1079209

PubChem CID: 46882023

Max Phase: Preclinical

Molecular Formula: C20H25N5

Molecular Weight: 335.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CC[C@@H](N)C2)c2c(n1)C1(CCC2)Cc2ccccc2C1

Standard InChI:  InChI=1S/C20H25N5/c21-15-7-9-25(12-15)18-16-6-3-8-20(17(16)23-19(22)24-18)10-13-4-1-2-5-14(13)11-20/h1-2,4-5,15H,3,6-12,21H2,(H2,22,23,24)/t15-/m1/s1

Standard InChI Key:  UCCUGVOBSDLCCJ-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    5.9151  -25.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6984  -25.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212  -26.4220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6266  -24.7340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0569  -25.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0537  -24.7297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3382  -24.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3354  -23.4960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7723  -25.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376  -25.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258  -25.5618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9103  -26.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6220  -27.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3388  -26.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8628  -26.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6700  -26.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0810  -26.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5276  -25.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0072  -27.7161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5757  -25.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726  -25.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3531  -24.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5368  -24.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2426  -25.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7639  -26.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 21  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
  9 15  1  0
 20  3  1  0
  6  7  2  0
  7  4  1  0
  3  1  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  9  1  0
  7  8  1  0
 16 19  1  1
  1  2  1  0
  5  9  1  0
 20 21  2  0
 10 11  1  0
 21 22  1  0
  4 11  2  0
 22 23  2  0
 23 24  1  0
 10  5  2  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1079209

   4'-[(3R)-3-aminopyrrolidin-1-yl]spiro[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: 335.45

Molecular Weight (Monoisotopic): 335.2110

AlogP: 1.97

#Rotatable Bonds: 1

Polar Surface Area: 81.06

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.83

CX LogP: 3.36

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.39

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