(S)-2-(3-(3-(tert-butyl)-4-((4-(trifluoromethyl)benzyl)oxy)phenyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboximidamide hydrochloride

ID: ALA4570134

PubChem CID: 155564368

Max Phase: Preclinical

Molecular Formula: C25H29ClF3N5O2

Molecular Weight: 487.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(-c2noc([C@@H]3CCCN3C(=N)N)n2)ccc1OCc1ccc(C(F)(F)F)cc1.Cl

Standard InChI:  InChI=1S/C25H28F3N5O2.ClH/c1-24(2,3)18-13-16(21-31-22(35-32-21)19-5-4-12-33(19)23(29)30)8-11-20(18)34-14-15-6-9-17(10-7-15)25(26,27)28;/h6-11,13,19H,4-5,12,14H2,1-3H3,(H3,29,30);1H/t19-;/m0./s1

Standard InChI Key:  AGZNVEMVNPCKSX-FYZYNONXSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
   14.9667   -3.8073    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9904   -5.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048   -8.5476    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9380   -7.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7507   -3.0737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7748   -5.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1841   -5.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3552   -3.3805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2237   -8.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7325   -4.4306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4043   -5.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5104   -6.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091   -7.7292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.5389   -4.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3685   -7.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242   -8.9663    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.2234   -5.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6571   -8.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0736   -4.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6517   -5.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2252   -6.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6533   -6.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5116   -5.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3667   -6.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1415   -3.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7956   -6.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9391   -6.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9540   -4.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9416   -6.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9388   -5.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3187   -4.4357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815   -6.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2250   -7.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5172   -8.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9326   -8.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2190   -8.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 21 29  2  0
 29 30  1  0
 12 21  1  0
 26 32  1  0
  2 19  1  0
 23 12  2  0
 25  8  1  0
 15 24  1  0
 11 28  2  0
 10 20  2  0
 28 14  1  0
  9 13  1  0
  7  2  1  0
 20 11  1  0
  4 18  1  0
  6 28  1  1
 19 31  1  0
  4  9  1  0
 17 23  1  0
 12 26  1  0
 31 25  1  0
 18 15  2  0
 30 17  2  0
  9 16  1  0
 22 27  1  0
 32 24  1  0
 24 22  2  0
 30 20  1  0
 14 10  1  0
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  9  3  1  0
 25  5  2  0
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 21 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
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: 487.53

Molecular Weight (Monoisotopic): 487.2195

AlogP: 5.66

#Rotatable Bonds: 5

Polar Surface Area: 101.26

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.10

CX LogP: 6.37

CX LogD: 3.91

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: -1.18

References

1. Sibley CD, Morris EA, Kharel Y, Brown AM, Huang T, Bevan DR, Lynch KR, Santos WL..  (2020)  Discovery of a Small Side Cavity in Sphingosine Kinase 2 that Enhances Inhibitor Potency and Selectivity.,  63  (3): [PMID:31895563] [10.1021/acs.jmedchem.9b01508]

Source

Source(1):

• Scientific Literature