6-(4-Phenylpiperazine-1-yl)-9-(beta-D-ribofuranosyl)-9H-purine

ID: ALA2042164

PubChem CID: 44776615

Max Phase: Preclinical

Molecular Formula: C20H24N6O4

Molecular Weight: 412.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](n2cnc3c(N4CCN(c5ccccc5)CC4)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C20H24N6O4/c27-10-14-16(28)17(29)20(30-14)26-12-23-15-18(21-11-22-19(15)26)25-8-6-24(7-9-25)13-4-2-1-3-5-13/h1-5,11-12,14,16-17,20,27-29H,6-10H2/t14-,16-,17-,20-/m1/s1

Standard InChI Key:  FVRJZHPJEJJPPT-WVSUBDOOSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   -3.9885   -3.1997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9897   -4.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750   -4.4398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -2.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -3.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5612   -4.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -4.2836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2825   -3.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -2.9390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2792   -1.9620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642   -1.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5647   -0.7268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2785   -0.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934   -0.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946   -1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -5.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4129   -5.6119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1417   -6.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3169   -6.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0784   -5.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -7.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4346   -6.9991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2987   -5.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8182   -7.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2767    0.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    0.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5594    1.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740    2.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9885    0.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  5  4  2  0
 16  7  1  1
 16 17  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  4  1  1  0
 18 21  1  1
  4 10  1  0
 21 22  1  0
 10 11  1  0
 20 23  1  6
  5  6  1  0
 19 24  1  6
  2  3  1  0
 25 26  2  0
  3  6  2  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 10 15  1  0
 28 29  1  0
 11 12  1  0
 29 30  2  0
 30 25  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2042164

   (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(4-phenylpiperazin-1-yl)-9H-purin-9-yl]tetrahydrofuran-3,4-diol

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: 412.45

Molecular Weight (Monoisotopic): 412.1859

AlogP: -0.24

#Rotatable Bonds: 4

Polar Surface Area: 120.00

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.69

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: 0.03

References

1. Tuncbilek M, Guven EB, Onder T, Cetin Atalay R..  (2012)  Synthesis of novel 6-(4-substituted piperazine-1-yl)-9-(β-D-ribofuranosyl)purine derivatives, which lead to senescence-induced cell death in liver cancer cells.,  55  (7): [PMID:22409771] [10.1021/jm3001532]

2. Crespo RA, Dang Q, Zhou NE, Guthrie LM, Snavely TC, Dong W, Loesch KA, Suzuki T, You L, Wang W, O'Malley T, Parish T, Olsen DB, Sacchettini JC..  (2019)  Structure-Guided Drug Design of 6-Substituted Adenosine Analogues as Potent Inhibitors of Mycobacterium tuberculosis Adenosine Kinase.,  62  (9): [PMID:31002508] [10.1021/acs.jmedchem.9b00020]

Source

Source(1):

• Scientific Literature