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

ID: ALA1078018

PubChem CID: 46882020

Max Phase: Preclinical

Molecular Formula: C17H27N5

Molecular Weight: 301.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CC[C@@H](N)C2)c2c(n1)C1(CCCCC1)CCC2

Standard InChI:  InChI=1S/C17H27N5/c18-12-6-10-22(11-12)15-13-5-4-9-17(7-2-1-3-8-17)14(13)20-16(19)21-15/h12H,1-11,18H2,(H2,19,20,21)/t12-/m1/s1

Standard InChI Key:  QASWJHPAQLSMRO-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    4.2250  -20.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208  -19.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5082  -19.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7952  -19.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7994  -20.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5166  -20.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9396  -19.0024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3700  -19.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668  -18.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6512  -18.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484  -17.7643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0854  -20.2396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6506  -20.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9388  -19.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232  -21.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9350  -21.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6518  -21.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1759  -21.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9832  -21.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3942  -20.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8408  -19.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3204  -21.9847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 10 11  1  0
  4  5  1  0
  8 12  1  0
 13 14  1  0
  5  6  1  0
  7 14  2  0
  1  2  1  0
 13  8  2  0
 13 17  1  0
 14  1  1  0
  1 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
  1  6  1  0
  8  9  1  0
  2  3  1  0
  9 10  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 12  1  0
 10  7  1  0
 19 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1078018

   4-[(3R)-3-aminopyrrolidin-1-yl]spiro[6,7-dihydro-5H-quinazoline-8,1'-cyclohexane]-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: 301.44

Molecular Weight (Monoisotopic): 301.2266

AlogP: 2.13

#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: 3.05

CX LogD: 0.54

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -0.36

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