3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(hydroxy)methyl)-1-phenylpiperidin-2-one

ID: ALA2271066

PubChem CID: 76315988

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)OCCO3)CCCN1c1ccccc1

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

Standard InChI Key:  RCTOVIDBDPFVSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   21.2290  -17.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2279  -18.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9359  -18.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9342  -17.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6428  -17.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6416  -18.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3478  -18.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0597  -18.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0609  -17.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3501  -17.2782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5212  -17.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5210  -16.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8136  -17.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1056  -17.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4001  -17.6897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3961  -18.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1037  -18.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8154  -18.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1067  -16.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6939  -17.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6999  -16.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9945  -16.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2844  -16.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2841  -17.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9901  -17.6863    0.0000 C   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
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14 19  2  0
 15 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271066

   3-[2,3-Dihydro-1,4-benzodioxin-6-yl(hydroxy)methyl]-1-phenylpiperidin-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: 2.93

#Rotatable Bonds: 3

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: 13.96

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.93

Np Likeness Score: -0.38

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