3-(benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)-1-benzylpiperidin-2-one

ID: ALA2271052

PubChem CID: 76330580

Max Phase: Preclinical

Molecular Formula: C20H21NO4

Molecular Weight: 339.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(C(O)c2ccc3c(c2)OCO3)CCCN1Cc1ccccc1

Standard InChI:  InChI=1S/C20H21NO4/c22-19(15-8-9-17-18(11-15)25-13-24-17)16-7-4-10-21(20(16)23)12-14-5-2-1-3-6-14/h1-3,5-6,8-9,11,16,19,22H,4,7,10,12-13H2

Standard InChI Key:  NIYKVGNJZHJFHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   28.3980  -20.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3969  -21.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1049  -21.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8146  -21.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8118  -20.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1032  -20.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5179  -20.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2272  -20.5653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2277  -21.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9328  -21.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6414  -21.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6403  -20.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9306  -20.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9266  -19.3321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3479  -20.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0557  -20.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3476  -19.3336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0519  -21.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7557  -21.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7590  -20.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4703  -20.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4653  -21.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2401  -21.6317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7242  -20.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2483  -20.3108    0.0000 O   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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 16 18  2  0
 16 20  1  0
 18 19  1  0
 19 22  2  0
 21 20  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271052

   3-[1,3-Benzodioxol-5-yl(hydroxy)methyl]-1-benzylpiperidin-2-one

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: 339.39

Molecular Weight (Monoisotopic): 339.1471

AlogP: 2.89

#Rotatable Bonds: 4

Polar Surface Area: 59.00

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.94

CX Basic pKa: ┄

CX LogP: 2.48

CX LogD: 2.48

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.93

Np Likeness Score: -0.11

References

1. TSUKADA H, YAMADA N, HASHIMOTO K, TANIGUCHI E, KUWANO E.  (2001)  Inhibitory Activity of N-Substituted-2-piperidones with a 1, 4-Benzodioxan Ring on Germination of Barnyardgrass,  26  (2): [10.1584/jpestics.26.143]

Source

Source(1):

• Scientific Literature