1-(4-Benzylpiperidin-1-yl)-2-(5,6-dihydroxy-1H-indol-3-yl)ethane-1,2-dione

ID: ALA3103130

PubChem CID: 76328242

Max Phase: Preclinical

Molecular Formula: C22H22N2O4

Molecular Weight: 378.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(C(=O)N1CCC(Cc2ccccc2)CC1)c1c[nH]c2cc(O)c(O)cc12

Standard InChI:  InChI=1S/C22H22N2O4/c25-19-11-16-17(13-23-18(16)12-20(19)26)21(27)22(28)24-8-6-15(7-9-24)10-14-4-2-1-3-5-14/h1-5,11-13,15,23,25-26H,6-10H2

Standard InChI Key:  YCFGDBMCZVEZAB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   13.6984  -10.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4096  -10.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6989   -9.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1122  -10.2584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1108  -12.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8174  -11.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4508  -11.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1375  -11.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9278  -11.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5040  -12.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2939  -13.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5076  -13.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9274  -12.7168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8741  -13.6576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2943  -12.0782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9908  -10.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9944  -11.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2868  -11.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5796  -11.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5771  -10.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2847  -10.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8730  -11.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1619  -11.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4543  -11.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7482  -11.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7446  -10.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4522  -10.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1594  -10.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  2  4  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  5 13  1  0
  8 13  2  0
 11 14  1  0
 10 15  1  0
  2  7  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 16 21  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 19 22  1  0
  1 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103130

   1-(4-benzylpiperidin-1-yl)-2-(5,6-dihydroxy-1H-indol-3-yl)ethane-1,2-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: 378.43

Molecular Weight (Monoisotopic): 378.1580

AlogP: 3.24

#Rotatable Bonds: 4

Polar Surface Area: 93.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.44

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -0.23

References

1. Gitto R, De Luca L, Ferro S, Russo E, De Sarro G, Chisari M, Ciranna L, Alvarez-Builla J, Alajarin R, Buemi MR, Chimirri A..  (2014)  Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors.,  22  (3): [PMID:24411196] [10.1016/j.bmc.2013.12.040]

2. 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