Cis-N,N'-((Diazene-1,2-diylbis(3,5-difluoro-4,1-phenylene))bis-(methylene))bis(4-((4,5-dihydroisoxazol-3-yl)oxy)-N,N-dimethylbut-2-yn-1-aminium)Bromide

ID: ALA4514215

Max Phase: Preclinical

Molecular Formula: C32H36Br2F4N6O4

Molecular Weight: 644.67

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[N+](C)(CC#CCOC1=NOCC1)Cc1cc(F)c(/N=N\c2c(F)cc(C[N+](C)(C)CC#CCOC3=NOCC3)cc2F)c(F)c1.[Br-].[Br-]

Standard InChI:  InChI=1S/C32H36F4N6O4.2BrH/c1-41(2,11-5-7-13-43-29-9-15-45-39-29)21-23-17-25(33)31(26(34)18-23)37-38-32-27(35)19-24(20-28(32)36)22-42(3,4)12-6-8-14-44-30-10-16-46-40-30;;/h17-20H,9-16,21-22H2,1-4H3;2*1H/q+2;;/p-2/b38-37-;;

Standard InChI Key:  JGURFMYKGKJPFD-VJZPTIJGSA-L

Molfile:  

     RDKit          2D

 48 49  0  0  0  0  0  0  0  0999 V2000
   39.6316   -8.1375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   33.7100  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4286  -11.0081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1472  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8659  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5830  -11.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3040  -11.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0203  -11.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0156  -10.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6754  -10.0889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4160   -9.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5868   -9.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3364  -10.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4286  -11.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7037  -11.4165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7078   -9.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4240   -9.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4222   -8.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7055   -8.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9935   -8.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9988   -9.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7023   -7.2933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4150   -6.8780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2370   -6.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6488   -7.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4699   -7.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8790   -6.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4608   -6.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6411   -6.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7039   -6.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1127   -6.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.9377   -6.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3465   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7545   -4.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1633   -3.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9882   -3.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4045   -4.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0744   -5.4600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.6904   -6.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.4028   -5.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2268   -4.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6966   -5.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5202   -6.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1352   -8.1169    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.2764   -8.1311    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.2236   -5.4529    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.6411   -8.4124    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   35.4529   -9.7210    0.0000 Br  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
 27 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  3  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 37  1  0
 31 42  1  0
 31 43  1  0
 18 44  1  0
 20 45  1  0
 29 46  1  0
 25 47  1  0
M  CHG  4   1  -1   3   1  31   1  48  -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: 644.67

Molecular Weight (Monoisotopic): 644.2723

AlogP: 5.32

#Rotatable Bonds: 10

Polar Surface Area: 86.36

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.34

CX Basic pKa: 0.69

CX LogP: -2.46

CX LogD: -2.46

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.15

Np Likeness Score: -0.23

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