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

ID: ALA1081681

PubChem CID: 44231734

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-/m0/s1

Standard InChI Key:  VYKIJFGQXTUGSK-NSHDSACASA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   -4.3592  -15.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5759  -14.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4036  -14.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6986  -15.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0531  -16.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6477  -14.4597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173  -15.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2205  -14.4554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361  -14.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389  -13.2217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020  -15.6968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367  -15.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6485  -15.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3640  -16.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6523  -16.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355  -16.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4115  -16.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043  -16.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1933  -15.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466  -15.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671  -17.4418    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  6
M  END

Alternative Forms

1. Parent:

   

   ALA1081681

   4-[(3S)-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