(S)-8-(3-chloro-4-fluorobenzyl)-2,3-dicyclopropyl-6-hydroxy-2,3,9,10-tetrahydroimidazo[5,1-a][2,6]naphthyridine-1,5,7(8H)-trione

ID: ALA4078272

PubChem CID: 117743977

Max Phase: Preclinical

Molecular Formula: C23H21ClFN3O4

Molecular Weight: 457.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2c(c3n(c(=O)c2O)[C@@H](C2CC2)N(C2CC2)C3=O)CCN1Cc1ccc(F)c(Cl)c1

Standard InChI:  InChI=1S/C23H21ClFN3O4/c24-15-9-11(1-6-16(15)25)10-26-8-7-14-17(21(26)30)19(29)23(32)28-18(14)22(31)27(13-4-5-13)20(28)12-2-3-12/h1,6,9,12-13,20,29H,2-5,7-8,10H2/t20-/m0/s1

Standard InChI Key:  STNHOJJHMDPOJN-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
    1.7898   -3.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887   -4.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -5.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2064   -4.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2035   -3.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4949   -3.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147   -5.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218   -4.6304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3246   -5.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3243   -3.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -3.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3220   -5.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0325   -3.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0273   -4.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7300   -5.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4383   -4.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7258   -5.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1446   -5.0504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7362   -3.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4390   -3.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0392   -3.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7073   -2.5338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9021   -2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3533   -2.0156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8391   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4475   -3.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6148   -3.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820   -3.4051    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806   -5.0411    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1136   -1.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8163   -1.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1072   -1.0091    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
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  8 11  1  0
  9 14  1  0
 13 10  1  0
 10 11  1  0
  9 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 20  1  0
 19 13  2  0
 15 17  1  0
 16 18  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 23 24  2  0
 21 25  1  6
 26 25  1  0
 27 26  1  0
 25 27  1  0
  1 28  1  0
  2 29  1  0
 22 30  1  0
 31 30  1  0
 32 31  1  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4078272

   (3S)-8-[(3-chloro-4-fluorophenyl)methyl]-2,3-dicyclopropyl-6-hydroxy-9,10-dihydro-3H-imidazo[5,1-a][2,6]naphthyridine-1,5,7-trione

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: 457.89

Molecular Weight (Monoisotopic): 457.1205

AlogP: 3.07

#Rotatable Bonds: 4

Polar Surface Area: 82.85

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.08

CX Basic pKa: 0.26

CX LogP: 1.86

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.76

Np Likeness Score: -0.80

References

1. Schreier JD, Embrey MW, Raheem IT, Barbe G, Campeau LC, Dubost D, McCabe Dunn J, Grobler J, Hartingh TJ, Hazuda DJ, Klein D, Miller MD, Moore KP, Nguyen N, Pajkovic N, Powell DA, Rada V, Sanders JM, Sisko J, Steele TG, Wai J, Walji A, Xu M, Coleman PJ..  (2017)  Discovery and optimization of 2-pyridinone aminal integrase strand transfer inhibitors for the treatment of HIV.,  27  (9): [PMID:28285916] [10.1016/j.bmcl.2017.02.039]

Source

Source(1):

• Scientific Literature