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

ID: ALA388417

PubChem CID: 10406405

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cn(-c2ccc(O[C@@H]3CCN(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/t19-/m1/s1

Standard InChI Key:  WZGVPRAMPUCENN-LJQANCHMSA-N

Molfile:  

     RDKit          2D

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    2.6245   -5.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6216   -4.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -4.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932   -5.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1899   -4.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4049   -4.6808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0770   -5.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -6.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345   -4.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3314   -3.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0004   -3.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7484   -2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -3.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1595   -1.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6386   -1.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2270   -0.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980   -0.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4697   -1.7083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9832   -2.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7513   -2.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7166   -1.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9239   -1.0232    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  1
  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
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  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:

   

   ALA388417

   1-[4-[(3R)-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