2-((4-(1H-imidazol-1-yl)phenoxy)methyl)-1-(benzo[d][1,3]dioxol-5-ylmethyl)piperidine

ID: ALA233236

PubChem CID: 10069033

Max Phase: Preclinical

Molecular Formula: C23H25N3O3

Molecular Weight: 391.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(OCC3CCCCN3Cc3ccc4c(c3)OCO4)cc2)cn1

Standard InChI:  InChI=1S/C23H25N3O3/c1-2-11-25(14-18-4-9-22-23(13-18)29-17-28-22)20(3-1)15-27-21-7-5-19(6-8-21)26-12-10-24-16-26/h4-10,12-13,16,20H,1-3,11,14-15,17H2

Standard InChI Key:  OGIDTPKJWIUESB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.5576  -14.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5548  -14.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412  -13.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1300  -14.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267  -14.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3437  -13.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8630  -14.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3490  -15.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2659  -13.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2628  -12.7966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484  -11.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484  -12.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9771  -12.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9771  -11.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2628  -11.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6933  -12.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917  -13.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3996  -14.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3996  -14.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1109  -15.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8293  -14.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8320  -14.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1160  -13.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5419  -15.2850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6642  -16.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4732  -16.2388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8557  -15.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2843  -14.9229    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
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  6  7  1  0
 14 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  1  0
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  9  5  1  0
 19 20  2  0
  4  6  1  0
 20 21  1  0
  3 10  1  0
 21 22  2  0
  5  6  2  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
 24 19  1  0
 12 13  1  0
 22 25  1  0
 25 26  1  0
  1  2  2  0
  5  1  1  0
  2  3  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA233236

   2-((4-(1H-imidazol-1-yl)phenoxy)methyl)-1-(benzo[d][1,3]dioxol-5-ylmethyl)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: 391.47

Molecular Weight (Monoisotopic): 391.1896

AlogP: 4.03

#Rotatable Bonds: 6

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: 8.29

CX LogP: 3.86

CX LogD: 2.90

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -1.29

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