1-benzyl-3-(hydroxy(8-methoxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)piperidin-2-one

ID: ALA2271070

PubChem CID: 76326908

Max Phase: Preclinical

Molecular Formula: C22H25NO5

Molecular Weight: 383.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(O)C2CCCN(Cc3ccccc3)C2=O)cc2c1OCCO2

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

Standard InChI Key:  VUDXYLUTAZGKHJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   19.4877  -14.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2025  -14.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9188  -14.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9160  -13.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2007  -12.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6289  -12.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3448  -13.3692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3453  -14.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0572  -14.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7724  -14.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7713  -13.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0549  -12.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0508  -12.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4856  -12.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2001  -13.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4853  -12.1257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9102  -12.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9068  -14.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1989  -14.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6271  -13.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6231  -14.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3313  -14.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0481  -14.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0522  -13.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3394  -12.9505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9055  -15.4244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1904  -15.8357    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
 19 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271070

   1-Benzyl-3-[hydroxy-(5-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: 13.91

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.86

Np Likeness Score: -0.06

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