1-(5,6-dihydroxy-1H-indol-3-yl)-3-(4-(4-fluorobenzyl)piperidin-1-yl)propan-1-one

ID: ALA4247561

PubChem CID: 145984075

Max Phase: Preclinical

Molecular Formula: C23H25FN2O3

Molecular Weight: 396.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCN1CCC(Cc2ccc(F)cc2)CC1)c1c[nH]c2cc(O)c(O)cc12

Standard InChI:  InChI=1S/C23H25FN2O3/c24-17-3-1-15(2-4-17)11-16-5-8-26(9-6-16)10-7-21(27)19-14-25-20-13-23(29)22(28)12-18(19)20/h1-4,12-14,16,25,28-29H,5-11H2

Standard InChI Key:  IXICVSDLXZDCTE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    3.5851   -6.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5840   -7.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -7.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903   -6.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9989   -6.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0037   -7.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -7.5019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2611   -6.8368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8773   -6.0300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8760   -7.6660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0239   -5.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8222   -5.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4735   -4.7947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0702   -4.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8685   -4.2709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4140   -4.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2092   -4.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4613   -3.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9118   -3.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101   -3.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2603   -3.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5112   -2.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3105   -2.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5615   -2.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0132   -1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2107   -1.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9634   -2.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2631   -0.6451    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
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
  2 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4247561

   ---

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: 396.46

Molecular Weight (Monoisotopic): 396.1849

AlogP: 4.25

#Rotatable Bonds: 6

Polar Surface Area: 76.56

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.20

CX Basic pKa: 11.78

CX LogP: 3.21

CX LogD: 2.73

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -0.49

References

1. Ferro S, Gitto R, Buemi MR, Karamanou S, Stevaert A, Naesens L, De Luca L..  (2018)  Identification of influenza PA-Nter endonuclease inhibitors using pharmacophore- and docking-based virtual screening.,  26  (15): [PMID:30082105] [10.1016/j.bmc.2018.07.046]

Source

Source(1):

• Scientific Literature