Isavuconazonium

ID: ALA5289346

Max Phase: Preclinical

Molecular Formula: C35H39F2N8O5S+

Molecular Weight: 721.81

Names and Identifiers

Canonical SMILES:  CNCC(=O)OCc1cccnc1N(C)C(=O)OC(C)[n+]1cnn(C[C@](O)(c2cc(F)ccc2F)[C@@H](C)C2NC(c3ccc(C#N)cc3)CS2)c1

Standard InChI:  InChI=1S/C35H39F2N8O5S/c1-22(33-42-30(18-51-33)25-9-7-24(15-38)8-10-25)35(48,28-14-27(36)11-12-29(28)37)19-45-21-44(20-41-45)23(2)50-34(47)43(4)32-26(6-5-13-40-32)17-49-31(46)16-39-3/h5-14,20-23,30,33,39,42,48H,16-19H2,1-4H3/q+1/t22-,23?,30?,33?,35+/m0/s1

Standard InChI Key:  SNTMUKYILKWQLL-MKTVMHMXSA-N

Molfile:  

 
     RDKit          2D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -0.9584    0.7163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705   -0.5530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5464   -0.5530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2884    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    1.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    2.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689    3.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689    4.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    4.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8965    4.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6124    4.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3241    4.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3241    3.1885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399    4.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516    4.0126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4674    4.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    5.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689    5.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    5.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    4.4246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    2.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    3.1885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701    1.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7834   -1.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -1.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0220   -1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -2.6984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884   -2.7847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6167   -3.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3315   -4.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9449   -3.4525    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -4.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862   -3.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -4.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -4.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -5.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -4.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -0.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243   -0.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7523   -0.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7523   -0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0415    0.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243   -0.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    0.3869    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4674   -1.2685    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479   -1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2415   -5.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -5.6565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  3  4  1  0
  5  1  1  0
  4  5  2  0
  6  1  1  0
  7  6  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  2  0
 16 14  1  0
 17 16  1  0
 18 17  1  0
 19 11  2  0
 20 19  1  0
 20 21  2  0
 22 10  2  0
 21 22  1  0
 23  9  1  0
 24  8  2  0
 25  6  1  0
  3 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 30 29  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 34 31  1  0
 35 34  2  0
 36 35  1  0
 37 36  2  0
 38 37  1  0
 34 39  1  0
 39 38  2  0
 27 40  1  6
 27 41  1  0
 42 41  2  0
 43 42  1  0
 44 43  2  0
 45 44  1  0
 46 45  2  0
 41 46  1  0
 46 47  1  0
 43 48  1  0
 28 49  1  6
 50 37  1  0
 50 51  3  0
M  CHG  1   1   1
M  END

Alternative Forms

1. Parent:

   

   ALA5289346

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 721.81

Molecular Weight (Monoisotopic): 721.2727

AlogP: 3.70

#Rotatable Bonds: 13

Polar Surface Area: 158.51

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.82

CX Basic pKa: 7.51

CX LogP: -0.12

CX LogD: -0.51

Aromatic Rings: 4

Heavy Atoms: 51

QED Weighted: 0.14

Np Likeness Score: -0.80

References

1. Hall A, Chanteux H, Ménochet K, Ledecq M, Schulze MED..  (2021)  Designing Out PXR Activity on Drug Discovery Projects: A Review of Structure-Based Methods, Empirical and Computational Approaches.,  64  (10.0): [PMID:34003642] [10.1021/acs.jmedchem.0c02245]

Source

Source(1):

• Scientific Literature