1-((S)-6,11-dihydrodibenzo[b,e]thiepin-11-yl)-5-hydroxy-3-((R)-1,1,1-trifluoropropan-2-yl)-2,3-dihydro-1H-pyrido[1,2-f][1,2,4]triazine-4,6-dione

ID: ALA4103104

Cas Number: 1370241-45-4

PubChem CID: 68097023

Max Phase: Preclinical

Molecular Formula: C24H20F3N3O3S

Molecular Weight: 487.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](N1CN([C@H]2c3ccccc3CSc3ccccc32)n2ccc(=O)c(O)c2C1=O)C(F)(F)F

Standard InChI:  InChI=1S/C24H20F3N3O3S/c1-14(24(25,26)27)28-13-30(29-11-10-18(31)22(32)21(29)23(28)33)20-16-7-3-2-6-15(16)12-34-19-9-5-4-8-17(19)20/h2-11,14,20,32H,12-13H2,1H3/t14-,20+/m1/s1

Standard InChI Key:  XEOTUHPFOHTFEX-VLIAUNLRSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   10.3771   -9.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5178  -10.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2901  -10.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0049   -8.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6693  -10.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9248   -9.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7771   -9.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3482   -8.4333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1449   -8.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6257   -9.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4464   -9.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0415  -10.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8161  -10.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9922   -9.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3958   -8.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6536  -11.1045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6169  -12.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3382  -12.3521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3575  -11.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9149  -12.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9329  -11.5058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2400  -11.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5248  -11.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5068  -12.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2040  -12.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7898  -12.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1870  -13.5329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5982  -13.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0406  -12.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0222  -13.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7615  -12.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4598  -12.8084    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.1729  -11.7965    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.1635  -11.6685    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  7  4  2  0
  4  1  1  0
  5 11  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  6  7  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 16 21  1  0
 16 19  1  0
 20 17  1  0
 17 18  1  0
 18 19  1  0
  5 16  1  6
 20 21  1  0
 20 25  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 17 28  2  0
 29 18  1  1
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103104

   1-[(11S)-6,11-dihydrodibenzo[b,e]thiepin-11-yl]-5-hydroxy-3-[(2R)-1,1,1-trifluoropropan-2-yl]-2,3-dihydro-1H-pyrido[2,1-f][1,2,4]triazine-4,6-dione

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: 487.50

Molecular Weight (Monoisotopic): 487.1177

AlogP: 4.25

#Rotatable Bonds: 2

Polar Surface Area: 65.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.43

CX Basic pKa: ┄

CX LogP: 3.88

CX LogD: 3.88

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.59

Np Likeness Score: -0.43

References

1. Ju H, Zhang J, Huang B, Kang D, Huang B, Liu X, Zhan P..  (2017)  Inhibitors of Influenza Virus Polymerase Acidic (PA) Endonuclease: Contemporary Developments and Perspectives.,  60  (9): [PMID:28118010] [10.1021/acs.jmedchem.6b01227]

2. Taoda Y,Miyagawa M,Akiyama T,Tomita K,Hasegawa Y,Yoshida R,Noshi T,Shishido T,Kawai M.  (2020)  Dihydrodibenzothiepine: Promising hydrophobic pharmacophore in the influenza cap-dependent endonuclease inhibitor.,  30  (22): [PMID:32927030] [10.1016/j.bmcl.2020.127547]

Source

Source(1):

• Scientific Literature