9-(5-Iodo-2-isopropyl-4-methoxybenzyl)-N6-methyl-9Hpurine-2,6-diamine

ID: ALA2402580

PubChem CID: 71740793

Max Phase: Preclinical

Molecular Formula: C17H21IN6O

Molecular Weight: 452.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(N)nc2c1ncn2Cc1cc(I)c(OC)cc1C(C)C

Standard InChI:  InChI=1S/C17H21IN6O/c1-9(2)11-6-13(25-4)12(18)5-10(11)7-24-8-21-14-15(20-3)22-17(19)23-16(14)24/h5-6,8-9H,7H2,1-4H3,(H3,19,20,22,23)

Standard InChI Key:  ALEQEKDBZYEVEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    9.5779   -9.2793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5767  -10.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2916  -10.5195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2897   -8.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0051   -9.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0054  -10.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7958  -10.3633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2843   -9.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7954   -9.0187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2873   -8.0415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8619  -10.5186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0510  -11.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8580  -11.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1106  -12.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9168  -12.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4697  -11.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2106  -10.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4050  -10.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5577  -12.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7510  -12.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8117  -13.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2769  -11.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5330  -12.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7603  -10.2581    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    9.5715   -7.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
  2 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 14 19  1  0
 19 20  1  0
 19 21  1  0
 16 22  1  0
 22 23  1  0
 17 24  1  0
 10 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2402580

   9-[(5-iodo-4-methoxy-2-propan-2-ylphenyl)methyl]-6-N-methylpurine-2,6-diamine

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: 452.30

Molecular Weight (Monoisotopic): 452.0822

AlogP: 3.24

#Rotatable Bonds: 5

Polar Surface Area: 90.88

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.47

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.67

References

1. Lambertucci C, Sundukova M, Kachare DD, Panmand DS, Dal Ben D, Buccioni M, Marucci G, Marchenkova A, Thomas A, Nistri A, Cristalli G, Volpini R..  (2013)  Evaluation of adenine as scaffold for the development of novel P2X3 receptor antagonists.,  65  [PMID:23688699] [10.1016/j.ejmech.2013.04.037]

Source

Source(1):

• Scientific Literature