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

ID: ALA233030

PubChem CID: 10090102

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-/m0/s1

Standard InChI Key:  WZGVPRAMPUCENN-IBGZPJMESA-N

Molfile:  

     RDKit          2D

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   10.7661   -5.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7633   -5.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0479   -4.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3349   -5.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3315   -5.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5465   -4.8058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0647   -5.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5519   -6.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4762   -4.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4731   -3.8105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1421   -3.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8901   -2.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0587   -2.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059   -3.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3012   -1.8303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1280   -1.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5381   -2.5495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3683   -2.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7803   -1.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3687   -1.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5396   -1.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6114   -1.8333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1249   -2.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8929   -2.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8583   -1.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0656   -1.1482    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  6
  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:

   

   ALA233030

   1-[4-[(3S)-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