8-chloro-4-(tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)benzofuro[3,2-d]pyrimidine

ID: ALA1090520

PubChem CID: 46885129

Max Phase: Preclinical

Molecular Formula: C17H17ClN4O

Molecular Weight: 328.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc2oc3c(N4CC5CCCNC5C4)ncnc3c2c1

Standard InChI:  InChI=1S/C17H17ClN4O/c18-11-3-4-14-12(6-11)15-16(23-14)17(21-9-20-15)22-7-10-2-1-5-19-13(10)8-22/h3-4,6,9-10,13,19H,1-2,5,7-8H2

Standard InChI Key:  LAGRKYBBNRXFND-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
    0.3192   -6.2242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6952   -5.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6963   -6.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -6.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9837   -4.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -5.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638   -6.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725   -6.3260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4804   -4.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9904   -5.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1688   -5.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -4.8009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3310   -4.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1509   -4.2268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4093   -4.8349    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -7.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -6.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4062   -7.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7428   -7.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321   -8.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5839   -8.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2474   -8.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -7.3278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 11 12  2  0
 12 13  1  0
  3  4  1  0
 13 14  2  0
 14  9  1  0
 11  1  1  0
  4  7  2  0
  2 15  1  0
  1 16  1  0
  7  8  1  0
  8 10  1  0
 16 19  1  0
 18 17  1  0
 17  1  1  0
 18 19  1  0
  9  6  1  0
  2  3  2  0
  6  5  2  0
  9 10  2  0
  5  2  1  0
 10 11  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090520

   8-chloro-4-(tetrahydro-1H-pyrrolo[3,4-b]pyridin-6(2H,7H,7aH)-yl)benzofuro[3,2-d]pyrimidine

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: 328.80

Molecular Weight (Monoisotopic): 328.1091

AlogP: 3.22

#Rotatable Bonds: 1

Polar Surface Area: 54.19

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.47

CX LogP: 2.95

CX LogD: 0.91

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -0.53

References

1. Cramp S, Dyke HJ, Higgs C, Clark DE, Gill M, Savy P, Jennings N, Price S, Lockey PM, Norman D, Porres S, Wilson F, Jones A, Ramsden N, Mangano R, Leggate D, Andersson M, Hale R..  (2010)  Identification and hit-to-lead exploration of a novel series of histamine H4 receptor inverse agonists.,  20  (8): [PMID:20299215] [10.1016/j.bmcl.2010.02.097]

Source

Source(1):

• Scientific Literature