6-(3-chloro-4-fluorobenzyl)-4-hydroxy-2-isopropyl-N,N-dimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

ID: ALA1237000

Cas Number: 865298-83-5

PubChem CID: 54680316

Max Phase: Preclinical

Molecular Formula: C21H23ClFN3O4

Molecular Weight: 435.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)n1c(C(=O)N(C)C)c2c(c(O)c1=O)C(=O)N(Cc1ccc(F)c(Cl)c1)CC2

Standard InChI:  InChI=1S/C21H23ClFN3O4/c1-11(2)26-17(20(29)24(3)4)13-7-8-25(19(28)16(13)18(27)21(26)30)10-12-5-6-15(23)14(22)9-12/h5-6,9,11,27H,7-8,10H2,1-4H3

Standard InChI Key:  HFCJYZIWLQSWGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.2418    0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274    2.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    2.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    3.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8129    2.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -1.1389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274   -0.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984   -1.1389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -3.6139    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -2.7889    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739   -2.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4739   -1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450    0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984    2.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -2.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595   -1.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -2.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984   -0.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    0.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8129    0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274    1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3840    2.5736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450    0.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8129    0.9236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0
  2 27  1  0
  3 28  1  0
  4 28  1  0
 17  5  2  0
 18  6  2  0
 26  7  2  0
 22  8  1  0
 19  9  1  0
 21 10  1  0
 11 12  2  0
 11 19  1  0
 12 20  1  0
 13 20  2  0
 13 21  1  0
 14 15  1  0
 14 23  1  0
 15 29  1  0
 16 20  1  0
 16 29  1  0
 17 25  1  0
 17 28  1  0
 18 24  1  0
 18 29  1  0
 19 21  2  0
 22 24  2  0
 22 26  1  0
 23 24  1  0
 23 25  2  0
 25 30  1  0
 26 30  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1237000

   6-(3-Chloro-4-Fluorobenzyl)-4-Hydroxy-N,N-Dimethyl-2-(1-Methylethyl)-3,5-Dioxo-2,3,5,6,7,8-Hexahydro-2,6-Naphthyridine-1-Carboxamide

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: 435.88

Molecular Weight (Monoisotopic): 435.1361

AlogP: 2.83

#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: 8.23

CX Basic pKa: 0.08

CX LogP: 1.35

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.80

Np Likeness Score: -1.39

References

1. Raheem IT, Walji AM, Klein D, Sanders JM, Powell DA, Abeywickrema P, Barbe G, Bennet A, Childers K, Christensen M, Clas SD, Dubost D, Embrey M, Grobler J, Hafey MJ, Hartingh TJ, Hazuda DJ, Kuethe JT, McCabe Dunn J, Miller MD, Moore KP, Nolting A, Pajkovic N, Patel S, Peng Z, Rada V, Rearden P, Schreier JD, Sisko J, Steele TG, Truchon JF, Wai J, Xu M, Coleman PJ..  (2015)  Discovery of 2-Pyridinone Aminals: A Prodrug Strategy to Advance a Second Generation of HIV-1 Integrase Strand Transfer Inhibitors.,  58  (20): [PMID:26397965] [10.1021/acs.jmedchem.5b01037]

2. Wang Y, Gu SX, He Q, Fan R..  (2021)  Advances in the development of HIV integrase strand transfer inhibitors.,  225  [PMID:34425310] [10.1016/j.ejmech.2021.113787]

Source

Source(1):

• Scientific Literature