Cis-4-((4,5-Dihydroisoxazol-3-yl)oxy)-N,N-dimethyl-N-(4-(phenyldiazenyl)benzyl)but-2-yn-1-aminium Bromide

ID: ALA4536683

Max Phase: Preclinical

Molecular Formula: C22H25BrN4O2

Molecular Weight: 377.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[N+](C)(CC#CCOC1=NOCC1)Cc1ccc(/N=N\c2ccccc2)cc1.[Br-]

Standard InChI:  InChI=1S/C22H25N4O2.BrH/c1-26(2,15-6-7-16-27-22-14-17-28-25-22)18-19-10-12-21(13-11-19)24-23-20-8-4-3-5-9-20;/h3-5,8-13H,14-18H2,1-2H3;1H/q+1;/p-1/b24-23-;

Standard InChI Key:  IVNFEKIBQWIHFT-DCXSSQDFSA-M

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   13.1519  -23.9285    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.3311  -24.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0466  -25.0929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7620  -24.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4775  -25.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1915  -25.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9092  -25.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6225  -25.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6178  -24.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2746  -24.1778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0165  -23.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1909  -23.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9416  -24.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0466  -25.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3248  -25.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3290  -23.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0420  -23.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0402  -22.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3267  -22.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6177  -22.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6230  -23.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3234  -21.3903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0372  -20.9767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7543  -21.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7523  -22.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4686  -22.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1834  -22.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1774  -21.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4606  -20.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  1  0
  3 14  1  0
  3 15  1  0
 16  2  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  CHG  2   1  -1   3   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 377.47

Molecular Weight (Monoisotopic): 377.1972

AlogP: 4.43

#Rotatable Bonds: 6

Polar Surface Area: 55.54

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.76

CX LogP: 0.68

CX LogD: 0.68

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -0.34

References

1. Agnetta L, Bermudez M, Riefolo F, Matera C, Claro E, Messerer R, Littmann T, Wolber G, Holzgrabe U, Decker M..  (2019)  Fluorination of Photoswitchable Muscarinic Agonists Tunes Receptor Pharmacology and Photochromic Properties.,  62  (6): [PMID:30827105] [10.1021/acs.jmedchem.8b01822]

Source

Source(1):

• Scientific Literature