1-(4-(1-(benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-yloxy)phenyl)-1H-imidazole

ID: ALA388205

PubChem CID: 9863828

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(OC3CCN(Cc4ccc5c(c4)OCO5)C3)cc2)cn1

Standard InChI:  InChI=1S/C21H21N3O3/c1-6-20-21(26-15-25-20)11-16(1)12-23-9-7-19(13-23)27-18-4-2-17(3-5-18)24-10-8-22-14-24/h1-6,8,10-11,14,19H,7,9,12-13,15H2

Standard InChI Key:  WZGVPRAMPUCENN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.2130   -5.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2159   -5.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9355   -4.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6475   -5.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6525   -5.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4341   -4.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9189   -5.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4312   -6.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -4.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061   -3.8397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8371   -3.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -2.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204   -2.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1733   -3.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6780   -1.8594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8511   -1.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4410   -2.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108   -2.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1989   -1.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -1.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396   -1.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3678   -1.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1457   -2.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9138   -2.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8791   -1.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  3  4  2  0
 13 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  6  1  0
 20 21  1  0
  3 10  1  0
 21 22  2  0
 22 17  1  0
  5  6  2  0
 20 23  1  0
 23 24  1  0
 10 11  1  0
 11 12  1  0
  1  2  2  0
  5  1  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA388205

   1-[4-[1-(1,3-Benzodioxol-5-ylmethyl)pyrrolidin-3-yl]oxyphenyl]imidazole

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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 3.25

#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: 8.08

CX LogP: 2.89

CX LogD: 2.12

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -1.44

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