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

ID: ALA5288836

Max Phase: Preclinical

Molecular Formula: C27H29N3O4

Molecular Weight: 459.55

Names and Identifiers

Canonical SMILES:  O=C1c2cc(N3CCOCC3)c(Cc3ccccc3)nc2C(C2CCCO2)N1Cc1ccco1

Standard InChI:  InChI=1S/C27H29N3O4/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/h1-4,6-8,12,17,24,26H,5,9-11,13-16,18H2

Standard InChI Key:  NTRBETSWYBDVAH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
    0.6780    0.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926    0.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    1.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    1.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349    0.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337    1.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196    1.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067    1.0279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8216    0.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0774   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603   -0.6815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8616   -1.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793   -1.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5947   -1.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399    1.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2024    2.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131    3.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5264    2.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563    1.8306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727    2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022    1.8533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8161    1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252    1.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264    2.6761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8123    3.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    2.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1071   -0.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -1.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086   -2.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8230   -1.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8184   -1.0265    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  1  0
 13 14  1  0
 14 10  1  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:

   

   ALA5288836

   ---

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: 459.55

Molecular Weight (Monoisotopic): 459.2158

AlogP: 3.98

#Rotatable Bonds: 6

Polar Surface Area: 68.04

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: 2.66

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.56

Np Likeness Score: -0.97

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