9-(4-Aminobutyl)-6-(benzyloxy)-9H-purin-2-amine

ID: ALA5207999

PubChem CID: 168296835

Max Phase: Preclinical

Molecular Formula: C16H20N6O

Molecular Weight: 312.38

Names and Identifiers

Canonical SMILES:  NCCCCn1cnc2c(OCc3ccccc3)nc(N)nc21

Standard InChI:  InChI=1S/C16H20N6O/c17-8-4-5-9-22-11-19-13-14(22)20-16(18)21-15(13)23-10-12-6-2-1-3-7-12/h1-3,6-7,11H,4-5,8-10,17H2,(H2,18,20,21)

Standard InChI Key:  UURWATJCKKWXKH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -0.2023   -0.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -0.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3904   -0.8736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092   -1.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -1.2467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -0.0535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8176    0.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023    0.8649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607    0.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5585    0.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1427    0.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9290    1.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5119    2.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100    2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    1.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439    0.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6629   -0.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3783   -0.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -0.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -0.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5243   -0.4664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0230   -2.2582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  1  7  1  0
  7  8  1  0
  9  8  2  0
  2  9  1  0
  3 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 12 17  1  0
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  5 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5207999

   ---

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: 312.38

Molecular Weight (Monoisotopic): 312.1699

AlogP: 1.73

#Rotatable Bonds: 7

Polar Surface Area: 104.87

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.20

CX LogP: 1.72

CX LogD: -0.88

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -0.83

References

1. Franco Pinto J, Fillion A, Duchambon P, Bombard S, Granzhan A..  (2022)  Acridine-O⁶-benzylguanine hybrids: Synthesis, DNA binding, MGMT inhibition and antiproliferative activity.,  227  [PMID:34731767] [10.1016/j.ejmech.2021.113909]

Source

Source(1):

• Scientific Literature