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

ID: ALA232825

PubChem CID: 10068163

Max Phase: Preclinical

Molecular Formula: C22H23N3O3

Molecular Weight: 377.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(OC3CCCN(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

Standard InChI Key:  HHOPJGKEAIIIDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.5895    0.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3090    0.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0210   -0.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0260    0.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8077    0.4297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2925   -0.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8047   -0.9040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8765    0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8796    1.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    2.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1676    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1676    2.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8796    3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    3.0687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7427    1.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0303    1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3136    1.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139    2.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269    3.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5998    1.4062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5172    0.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895    0.4128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    1.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520    1.7405    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
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 14 15  1  0
 15 16  1  0
  6  7  1  0
 15 17  1  0
  7  8  1  0
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  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
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 27 28  2  0
 28 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA232825

   3-(4-(1H-imidazol-1-yl)phenoxy)-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: 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