1-benzyl-3-(hydroxy(7-methoxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)piperidin-2-one

ID: ALA2271069

PubChem CID: 76330585

Max Phase: Preclinical

Molecular Formula: C22H25NO5

Molecular Weight: 383.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1C(O)C1CCCN(Cc3ccccc3)C1=O)OCCO2

Standard InChI:  InChI=1S/C22H25NO5/c1-26-18-13-20-19(27-10-11-28-20)12-17(18)21(24)16-8-5-9-23(22(16)25)14-15-6-3-2-4-7-15/h2-4,6-7,12-13,16,21,24H,5,8-11,14H2,1H3

Standard InChI Key:  CWBXTSZZIXFNRG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   29.0738  -14.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7818  -14.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4915  -14.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4886  -13.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7800  -13.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1948  -13.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9040  -13.4128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9045  -14.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6097  -14.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3183  -14.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3172  -13.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6075  -12.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6034  -12.1796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0247  -12.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7326  -13.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0244  -12.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4359  -12.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4326  -14.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7314  -14.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1462  -13.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1421  -14.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8436  -14.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5537  -14.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5578  -13.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8518  -12.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0228  -14.6310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0210  -15.4482    0.0000 C   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 20  2  0
 16 18  1  0
 19 22  2  0
 21 18  2  0
 19 20  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 20 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271069

   1-Benzyl-3-[hydroxy-(6-methoxy-2,3-dihydro-1,4-benzodioxin-7-yl)methyl]piperidin-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: 383.44

Molecular Weight (Monoisotopic): 383.1733

AlogP: 2.94

#Rotatable Bonds: 5

Polar Surface Area: 68.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.72

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.86

Np Likeness Score: -0.21

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