6-((3-((dimethylamino)methyl)benzyl)oxy)-9H-purin-2-amine

ID: ALA2171205

PubChem CID: 71449867

Max Phase: Preclinical

Molecular Formula: C15H18N6O

Molecular Weight: 298.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1cccc(COc2nc(N)nc3[nH]cnc23)c1

Standard InChI:  InChI=1S/C15H18N6O/c1-21(2)7-10-4-3-5-11(6-10)8-22-14-12-13(18-9-17-12)19-15(16)20-14/h3-6,9H,7-8H2,1-2H3,(H3,16,17,18,19,20)

Standard InChI Key:  SGMHYUAQYLJKMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   22.2678  -29.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7507  -30.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2638  -31.1868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4800  -30.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7643  -31.3399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0510  -30.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0535  -30.1003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7691  -29.6899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4824  -30.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3353  -31.3357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7716  -28.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0583  -28.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3426  -28.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6294  -28.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9137  -28.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9113  -29.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6245  -30.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3402  -29.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2005  -28.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4848  -28.8523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7715  -28.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4823  -29.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
  6 10  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
 20 21  1  0
 20 22  1  0
 19 20  1  0
 15 19  1  0
 11 12  1  0
  8 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2171205

   6-[[3-[(dimethylamino)methyl]phenyl]methoxy]-7H-purin-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: 298.35

Molecular Weight (Monoisotopic): 298.1542

AlogP: 1.58

#Rotatable Bonds: 5

Polar Surface Area: 92.95

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: 8.58

CX LogP: 1.17

CX LogD: 0.23

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: -1.03

References

1. Zhu R, Seow HA, Baumann RP, Ishiguro K, Penketh PG, Shyam K, Sartorelli AC..  (2012)  Design of a hypoxia-activated prodrug inhibitor of O6-alkylguanine-DNA alkyltransferase.,  22  (19): [PMID:22932317] [10.1016/j.bmcl.2012.08.008]

Source

Source(1):

• Scientific Literature