2-benzyl-7-(furan-2-yl)-6-(furan-2-ylmethyl)-3-morpholino-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

ID: ALA5284092

Max Phase: Preclinical

Molecular Formula: C27H25N3O4

Molecular Weight: 455.51

Names and Identifiers

Canonical SMILES:  O=C1c2cc(N3CCOCC3)c(Cc3ccccc3)nc2C(c2ccco2)N1Cc1ccco1

Standard InChI:  InChI=1S/C27H25N3O4/c31-27-21-17-23(29-10-14-32-15-11-29)22(16-19-6-2-1-3-7-19)28-25(21)26(24-9-5-13-34-24)30(27)18-20-8-4-12-33-20/h1-9,12-13,17,26H,10-11,14-16,18H2

Standard InChI Key:  UDFJUGZZPADPPB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    0.6779   -0.2105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    1.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6761    1.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196    1.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3066    0.6164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8216   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0773   -0.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -1.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8614   -1.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -2.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5946   -1.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    0.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399    1.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2022    2.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    2.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5262    2.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561    1.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727    2.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021    1.4418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5251    1.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5262    2.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8122    2.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0970    2.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058   -0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071   -1.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1085   -2.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8228   -2.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183   -1.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  5  1  1  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  1  0
  7 21  2  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 22 27  1  0
 26 27  1  0
  2 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284092

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 455.51

Molecular Weight (Monoisotopic): 455.1845

AlogP: 4.44

#Rotatable Bonds: 6

Polar Surface Area: 71.95

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.17

CX Basic pKa: 2.30

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -1.13

References

1. Morales-Salazar I, Montes-Enríquez FP, Garduño-Albino CE, García-Sánchez MA, Ibarra IA, Rojas-Aguirre Y, García-Hernández ME, Sarmiento-Silva RE, Alcaraz-Estrada SL, Díaz-Cervantes E, González-Zamora E, Islas-Jácome A..  (2023)  Synthesis of bis-furyl-pyrrolo[3,4-b]pyridin-5-ones via Ugi-Zhu reaction and in vitro activity assays against human SARS-CoV-2 and in silico studies on its main proteins.,  14  (1.0): [PMID:36760742] [10.1039/d2md00350c]

Source

Source(1):

• Scientific Literature