4-amino-3-iodo-1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidine

ID: ALA4441282

Cas Number: 144928-33-6

PubChem CID: 446940

Max Phase: Preclinical

Molecular Formula: C10H12IN5O4

Molecular Weight: 393.14

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(I)nn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C10H12IN5O4/c11-7-4-8(12)13-2-14-9(4)16(15-7)10-6(19)5(18)3(1-17)20-10/h2-3,5-6,10,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,10-/m1/s1

Standard InChI Key:  BZFGDXJGWSIYQP-BHBWVORQSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    9.4555   -1.3350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4608   -2.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1783   -2.5674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1837   -3.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4755   -3.8079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7580   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7485   -2.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9643   -2.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7034   -1.5458    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    7.4850   -2.9965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9753   -3.6620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7242   -4.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2145   -5.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0401   -5.1064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7353   -5.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9960   -6.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9510   -5.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2856   -6.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3794   -6.8409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9458   -4.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
  6 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  1
 18 19  1  0
 17 20  1  0
 12 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4441282

   4-Amino-3-iodo-1(beta-d-ribofuranosyl)pyrazolo[3,4-d]-pyrimidine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 393.14

Molecular Weight (Monoisotopic): 392.9934

AlogP: -1.38

#Rotatable Bonds: 2

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 3.16

CX LogP: -1.19

CX LogD: -1.19

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.46

Np Likeness Score: 0.56

References

1. Toti KS, Osborne D, Ciancetta A, Boison D, Jacobson KA..  (2016)  South (S)- and North (N)-Methanocarba-7-Deazaadenosine Analogues as Inhibitors of Human Adenosine Kinase.,  59  (14): [PMID:27410258] [10.1021/acs.jmedchem.6b00689]

2. Spurr SS, Bayle ED, Yu W, Li F, Tempel W, Vedadi M, Schapira M, Fish PV..  (2016)  New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms.,  26  (18): [PMID:27485386] [10.1016/j.bmcl.2016.07.041]

3. Bouton J, Ferreira de Almeida Fiuza L, Cardoso Santos C, Mazzarella MA, Soeiro MNC, Maes L, Karalic I, Caljon G, Van Calenbergh S..  (2021)  Revisiting Pyrazolo[3,4-d]pyrimidine Nucleosides as Anti-Trypanosoma cruzi and Antileishmanial Agents.,  64  (7.0): [PMID:33784107] [10.1021/acs.jmedchem.1c00135]

Source

Source(1):

• Scientific Literature