1-(5-bromo-4-(furan-3-yl)-6-methylpyrimidin-2-yl)-3-(3-(pyrrolidin-1-yl)propyl)guanidine

ID: ALA5221033

PubChem CID: 168298759

Max Phase: Preclinical

Molecular Formula: C17H23BrN6O

Molecular Weight: 407.32

Names and Identifiers

Canonical SMILES:  Cc1nc(NC(=N)NCCCN2CCCC2)nc(-c2ccoc2)c1Br

Standard InChI:  InChI=1S/C17H23BrN6O/c1-12-14(18)15(13-5-10-25-11-13)22-17(21-12)23-16(19)20-6-4-9-24-7-2-3-8-24/h5,10-11H,2-4,6-9H2,1H3,(H3,19,20,21,22,23)

Standard InChI Key:  SEGPMIUUMUZBBF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -4.4677   -1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8802   -1.0188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3281   -0.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5744   -0.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607   -1.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8595   -0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8595    0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1466    0.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1466    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4314    0.4952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1415   -0.7428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -0.7386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149   -0.7386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4298   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1446   -0.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5744   -0.7386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3280   -0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -1.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676   -1.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6606   -1.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5744    0.9096    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
  5  1  2  0
  6  4  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
 10  8  2  0
 11 10  1  0
 12 11  2  0
  6 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
  7 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5221033

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 407.32

Molecular Weight (Monoisotopic): 406.1117

AlogP: 3.23

#Rotatable Bonds: 6

Polar Surface Area: 90.07

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.49

CX LogP: 2.54

CX LogD: 0.18

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.39

Np Likeness Score: -0.91

References

1. Morrill C, Friesen WJ, Babu S, Baiazitov RY, Du W, Karloff DB, Lee CS, Moon YC, Ren H, Sierra J, Tomizawa Y, Vazirani P, Welch EM, Xue X, Zhuo J..  (2022)  Guanidino quinazolines and pyrimidines promote readthrough of premature termination codons in cells with native nonsense mutations.,  76  [PMID:36150638] [10.1016/j.bmcl.2022.128989]

Source

Source(1):

• Scientific Literature