3'-Deoxy-7-deazaadinosine

ID: ALA2023963

PubChem CID: 97454

Max Phase: Preclinical

Molecular Formula: C11H14N4O3

Molecular Weight: 250.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1ccn2[C@@H]1O[C@H](CO)C[C@H]1O

Standard InChI:  InChI=1S/C11H14N4O3/c12-9-7-1-2-15(10(7)14-5-13-9)11-8(17)3-6(4-16)18-11/h1-2,5-6,8,11,16-17H,3-4H2,(H2,12,13,14)/t6-,8+,11+/m0/s1

Standard InChI Key:  GAKDEQRUZQIUER-FMTFEUNWSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    6.3960   -6.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9820   -6.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7656   -6.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0149   -7.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8410   -7.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3197   -7.9316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0990   -6.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4359   -5.9889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8845   -6.2300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5513   -6.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2216   -6.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9687   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3863   -4.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2124   -4.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9779   -4.0209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1518   -4.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7377   -4.7277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1462   -5.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  3  8  1  0
  7  9  1  1
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 12 18  2  0
  9 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2023963

   7-(3-Deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo(2,3-d)pyrimidin-4-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: 250.26

Molecular Weight (Monoisotopic): 250.1066

AlogP: -0.35

#Rotatable Bonds: 2

Polar Surface Area: 106.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.53

CX Basic pKa: 6.51

CX LogP: -0.59

CX LogD: -0.64

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.67

Np Likeness Score: 1.14

References

1. Mayhoub AS..  (2012)  Hepatitis C RNA-dependent RNA polymerase inhibitors: a review of structure-activity and resistance relationships; different scaffolds and mutations.,  20  (10): [PMID:22516671] [10.1016/j.bmc.2012.03.049]

2. 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]

3. Bouton J, Furquim d'Almeida A, Maes L, Caljon G, Van Calenbergh S, Hulpia F..  (2021)  Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.,  216  [PMID:33667845] [10.1016/j.ejmech.2021.113290]

4. Lin C, Jaén Batista DDG, Mazzeti AL, Donola Girão R, de Oliveira GM, Karalic I, Hulpia F, Soeiro MNC, Maes L, Caljon G, Van Calenbergh S..  (2022)  N⁶-modification of 7-Deazapurine nucleoside analogues as Anti-Trypanosoma cruzi and anti-Leishmania agents: Structure-activity relationship exploration and In vivo evaluation.,  231  [PMID:35144125] [10.1016/j.ejmech.2022.114165]

Source

Source(1):

• Scientific Literature