4'-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-2'-amine

ID: ALA1081682

PubChem CID: 46881969

Max Phase: Preclinical

Molecular Formula: C18H27N5

Molecular Weight: 313.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N2C[C@H]3CNC[C@H]3C2)c2c(n1)C1(CCCC1)CCC2

Standard InChI:  InChI=1S/C18H27N5/c19-17-21-15-14(4-3-7-18(15)5-1-2-6-18)16(22-17)23-10-12-8-20-9-13(12)11-23/h12-13,20H,1-11H2,(H2,19,21,22)/t12-,13+

Standard InChI Key:  XXLYCVCLLJFPNH-BETUJISGSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   13.2530  -15.9081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0363  -15.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2085  -15.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9135  -15.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5591  -16.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9646  -14.6732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3950  -15.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3918  -14.6689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6762  -14.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6734  -13.4351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1104  -15.9104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6756  -15.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9638  -15.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2482  -16.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9600  -17.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6768  -16.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2009  -16.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8658  -15.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4192  -16.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0129  -16.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5652  -17.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3131  -17.1690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2228  -16.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5958  -17.6083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8250  -15.4667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  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
 17 20  1  0
 19 18  1  0
 18 11  1  0
 19 20  1  0
  8  9  2  0
  9  6  1  0
  4  5  1  0
  9 10  1  0
  5  1  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
  7 11  1  0
 20 24  1  6
 12 13  1  0
 19 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1081682

   4-[(3aS,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-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: 313.45

Molecular Weight (Monoisotopic): 313.2266

AlogP: 1.86

#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: 11.12

CX LogP: 2.64

CX LogD: -0.65

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.83

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]

2. 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