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

ID: ALA1081680

PubChem CID: 44231733

Max Phase: Preclinical

Molecular Formula: C16H25N5

Molecular Weight: 287.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2CC[C@@H](N)C2)c2c(n1)C1(CCCC1)CCC2

Standard InChI:  InChI=1S/C16H25N5/c17-11-5-9-21(10-11)14-12-4-3-8-16(6-1-2-7-16)13(12)19-15(18)20-14/h11H,1-10,17H2,(H2,18,19,20)/t11-/m1/s1

Standard InChI Key:  VYKIJFGQXTUGSK-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   14.1437  -11.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9270  -10.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0993  -10.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8043  -11.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4499  -11.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8552   -9.8642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2856  -10.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2824   -9.8599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5668   -9.4512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5639   -8.6262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0009  -11.1013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5662  -11.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8545  -10.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1388  -11.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8506  -12.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5674  -11.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0914  -11.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8987  -12.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3096  -11.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7563  -10.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2359  -12.8463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  5  1  1  0
  7 11  1  0
 12 13  1  0
  1  2  1  0
  6 13  2  0
 12  7  2  0
  2  3  1  0
 12 16  1  0
 13  1  1  0
  1 14  1  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
  7  8  1  0
  3  4  1  0
  8  9  2  0
  9  6  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 11  1  0
  4  5  1  0
 18 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1081680

   4-[(3R)-3-aminopyrrolidin-1-yl]spiro[6,7-dihydro-5H-quinazoline-8,1'-cyclopentane]-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: 287.41

Molecular Weight (Monoisotopic): 287.2110

AlogP: 1.74

#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: 2.60

CX LogD: 0.09

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.82

Np Likeness Score: -0.37

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