(R)-3-(4-(1H-imidazol-1-yl)phenoxy)-1-(benzo[d][1,3]dioxol-5-ylmethyl)piperidine

ID: ALA232826

PubChem CID: 10384948

Max Phase: Preclinical

Molecular Formula: C22H23N3O3

Molecular Weight: 377.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(O[C@@H]3CCCN(Cc4ccc5c(c4)OCO5)C3)cc2)cn1

Standard InChI:  InChI=1S/C22H23N3O3/c1-2-20(28-19-6-4-18(5-7-19)25-11-9-23-15-25)14-24(10-1)13-17-3-8-21-22(12-17)27-16-26-21/h3-9,11-12,15,20H,1-2,10,13-14,16H2/t20-/m1/s1

Standard InChI Key:  HHOPJGKEAIIIDF-HXUWFJFHSA-N

Molfile:  

     RDKit          2D

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    3.1037   -0.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854    0.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -0.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6691   -0.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841    0.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895   -1.1185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137    0.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8106    1.2105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000    2.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5240    2.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2397    2.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9530    2.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9490    1.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6614    1.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780    1.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3778    2.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6648    2.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0918    1.1937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1745    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9812    0.2003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3948    0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8437    1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 12 16  1  0
 13 11  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
  6  7  1  0
 15 17  1  1
  7  8  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  6  1  0
 20 21  2  0
  3 10  1  0
 21 22  1  0
  5  6  2  0
 22 23  2  0
 23 18  1  0
 10 11  1  0
 21 24  1  0
 24 25  1  0
 12 13  1  0
  1  2  2  0
  5  1  1  0
  2  3  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA232826

   (3R)-3-[4-(imidazol-1-yl)phenoxy]-1-[(1,3-benzodioxol-5-yl)methy]piperidine

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: 377.44

Molecular Weight (Monoisotopic): 377.1739

AlogP: 3.64

#Rotatable Bonds: 5

Polar Surface Area: 48.75

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.05

CX LogP: 3.41

CX LogD: 2.66

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -1.33

References

1. Wei RG, Adler M, Davey D, Ho E, Mohan R, Polokoff M, Tseng JL, Whitlow M, Xu W, Yuan S, Phillips G..  (2007)  1-(1,3-Benzodioxol-5-ylmethyl)-3-[4-(1H-imidazol-1-yl)phenoxy]-piperidine analogs as potent and selective inhibitors of nitric oxide formation.,  17  (9): [PMID:17368901] [10.1016/j.bmcl.2007.02.053]

Source

Source(1):

• Scientific Literature