4-Amino-N1-(beta-D-ribofuranosyl)-pyrrolo[2,3-b]pyridine

ID: ALA4436060

Cas Number: 83683-90-3

PubChem CID: 128557

Max Phase: Preclinical

Molecular Formula: C12H15N3O4

Molecular Weight: 265.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ccnc2c1ccn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C12H15N3O4/c13-7-1-3-14-11-6(7)2-4-15(11)12-10(18)9(17)8(5-16)19-12/h1-4,8-10,12,16-18H,5H2,(H2,13,14)/t8-,9-,10-,12-/m1/s1

Standard InChI Key:  ICSYNCVSXUEZDG-DNRKLUKYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    5.5181   -3.0459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381   -3.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1743   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8388   -3.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5788   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -4.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7616   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0777   -2.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -3.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5817   -3.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2610   -4.3212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6684   -4.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0039   -4.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9816   -4.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2379   -2.8849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1903   -4.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332   -3.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -3.4627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  1  1  0
  4  3  2  0
  5  7  2  0
  6  2  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  8  1  0
 11  4  1  0
 12  3  1  0
 13 14  1  0
 14 12  2  0
  6 15  1  6
 16 11  1  0
  9 17  1  6
 10 18  1  1
  4  5  1  0
  9 10  1  0
 13 11  2  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4436060

   1-Deazatubercidin

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: 265.27

Molecular Weight (Monoisotopic): 265.1063

AlogP: -0.77

#Rotatable Bonds: 2

Polar Surface Area: 113.76

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: 7.74

CX LogP: -1.17

CX LogD: -1.60

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.57

Np Likeness Score: 1.02

References

1. Lin C, Hulpia F, da Silva CF, Batista DDGJ, Van Hecke K, Maes L, Caljon G, Soeiro MNC, Van Calenbergh S..  (2019)  Discovery of Pyrrolo[2,3-b]pyridine (1,7-Dideazapurine) Nucleoside Analogues as Anti-Trypanosoma cruzi Agents.,  62  (19): [PMID:31495177] [10.1021/acs.jmedchem.9b01275]

2. 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