4'-((4aR,7aR)-tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)-6',7'-dihydro-5'H-spiro[cyclohexane-1,8'-quinazolin]-2'-amine

ID: ALA1078019

PubChem CID: 46882021

Max Phase: Preclinical

Molecular Formula: C20H31N5

Molecular Weight: 341.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2C[C@H]3CCCN[C@H]3C2)c2c(n1)C1(CCCCC1)CCC2

Standard InChI:  InChI=1S/C20H31N5/c21-19-23-17-15(7-4-10-20(17)8-2-1-3-9-20)18(24-19)25-12-14-6-5-11-22-16(14)13-25/h14,16,22H,1-13H2,(H2,21,23,24)/t14-,16+/m1/s1

Standard InChI Key:  ZLVKGQQLZNLETP-ZBFHGGJFSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
   12.2034  -20.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1992  -19.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4857  -19.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7717  -19.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7759  -20.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4941  -21.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9189  -19.4360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3512  -20.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3480  -19.4317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6314  -19.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6286  -18.1963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0675  -20.6748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6308  -20.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9181  -20.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2016  -21.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9143  -21.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6320  -21.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1581  -21.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8239  -20.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3780  -20.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9641  -21.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3712  -22.3740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1939  -22.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6079  -21.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1992  -20.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5452  -22.3749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7844  -20.2305    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  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
 18 21  1  0
 20 19  1  0
 19 12  1  0
 20 21  1  0
  2  3  1  0
  9 10  2  0
 10  7  1  0
  3  4  1  0
 10 11  1  0
  4  5  1  0
 20 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  8 12  1  0
 21 26  1  6
 13 14  1  0
 20 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1078019

   4-[(4aR,7aR)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-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: 341.50

Molecular Weight (Monoisotopic): 341.2579

AlogP: 2.79

#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: 9.57

CX LogP: 3.93

CX LogD: 1.64

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: 0.14

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