2-{[2-((S)-1-Hydroxymethylpropylamino)-9-isopropyl-9Hpurin-6-ylamino]-methyl}-6-methoxyphenol

ID: ALA2349190

PubChem CID: 71579157

Max Phase: Preclinical

Molecular Formula: C20H28N6O3

Molecular Weight: 400.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](CO)Nc1nc(NCc2cccc(OC)c2O)c2ncn(C(C)C)c2n1

Standard InChI:  InChI=1S/C20H28N6O3/c1-5-14(10-27)23-20-24-18(16-19(25-20)26(11-22-16)12(2)3)21-9-13-7-6-8-15(29-4)17(13)28/h6-8,11-12,14,27-28H,5,9-10H2,1-4H3,(H2,21,23,24,25)/t14-/m0/s1

Standard InChI Key:  RZRAYJQSPLLFCR-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   12.5543   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3418   -6.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5543   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8377   -6.9418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3418   -5.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1251   -5.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1251   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8377   -5.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8294   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8293   -4.4626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4043   -6.9418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6002   -7.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5501   -4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5419   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -6.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -6.5293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0418   -8.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4043   -7.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9793   -6.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8252   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2502   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -5.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9668   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2418   -2.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8168   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5293   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1158   -3.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1000   -1.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0953   -0.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  3  1  0
  6  7  2  0
  7  4  1  0
  8  3  2  0
  9  2  1  0
 10  8  1  0
 11  7  1  0
 12  2  1  0
 13 10  1  0
 14 13  1  0
 15 11  1  0
 16 19  1  0
 17 12  1  0
 18 12  1  0
 19 15  1  0
 20 14  2  0
 21 14  1  0
 15 22  1  6
 23 22  1  0
 24 21  2  0
 25 20  1  0
 26 24  1  0
  8  6  1  0
  9  5  2  0
 25 26  2  0
 20 27  1  0
 25 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2349190

   2-[[[2-[[(2S)-1-hydroxybutan-2-yl]amino]-9-propan-2-ylpurin-6-yl]amino]methyl]-6-methoxyphenol

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: 400.48

Molecular Weight (Monoisotopic): 400.2223

AlogP: 2.92

#Rotatable Bonds: 9

Polar Surface Area: 117.35

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.69

CX Basic pKa: 5.20

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -0.54

References

1. Zatloukal M, Jorda R, Gucký T, Řezníčková E, Voller J, Pospíšil T, Malínková V, Adamcová H, Kryštof V, Strnad M..  (2013)  Synthesis and in vitro biological evaluation of 2,6,9-trisubstituted purines targeting multiple cyclin-dependent kinases.,  61  [PMID:22770608] [10.1016/j.ejmech.2012.06.036]

2. Sharma S, Singh J, Ojha R, Singh H, Kaur M, Bedi PMS, Nepali K..  (2016)  Design strategies, structure activity relationship and mechanistic insights for purines as kinase inhibitors.,  112  [PMID:26907156] [10.1016/j.ejmech.2016.02.018]

Source

Source(1):

• Scientific Literature