2-((2-(4-(1H-imidazol-1-yl)phenoxy)ethyl)(benzo[d][1,3]dioxol-5-ylmethyl)amino)acetic acid

ID: ALA232422

PubChem CID: 9977997

Max Phase: Preclinical

Molecular Formula: C21H21N3O5

Molecular Weight: 395.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CN(CCOc1ccc(-n2ccnc2)cc1)Cc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C21H21N3O5/c25-21(26)13-23(12-16-1-6-19-20(11-16)29-15-28-19)9-10-27-18-4-2-17(3-5-18)24-8-7-22-14-24/h1-8,11,14H,9-10,12-13,15H2,(H,25,26)

Standard InChI Key:  RBLLHXYSENQZRS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.7198   -6.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7169   -6.9360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0055   -7.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2928   -6.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5773   -7.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8647   -6.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8620   -6.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1556   -5.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4362   -6.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7251   -5.6983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059   -4.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7956   -4.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4154   -5.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9809   -6.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7172   -8.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7138   -9.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396   -8.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1375   -9.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4301   -9.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6048  -10.6261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4197  -10.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7519   -9.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0069   -4.8669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2894   -6.0965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  3  4  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  4  5  1  0
  3 18  1  0
  2  3  1  0
 18 19  1  0
  5  6  1  0
 19 20  2  0
  7 12  1  0
 20 21  1  0
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  8  9  1  0
 23 22  2  0
 22 19  1  0
 23 24  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  1  2  1  0
 10 13  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 23  1  0
 13 14  1  0
  1 28  1  0
  6  7  1  0
  1 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA232422

   2-[1,3-Benzodioxol-5-ylmethyl-[2-(4-imidazol-1-ylphenoxy)ethyl]amino]acetic acid

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: 395.42

Molecular Weight (Monoisotopic): 395.1481

AlogP: 2.57

#Rotatable Bonds: 9

Polar Surface Area: 86.05

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.80

CX Basic pKa: 7.16

CX LogP: 0.32

CX LogD: 0.14

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -1.52

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