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

ID: ALA4548799

PubChem CID: 155548949

Max Phase: Preclinical

Molecular Formula: C21H20ClF4N5O2

Molecular Weight: 449.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cl.N=C(N)N1CCC[C@H]1c1nc(-c2ccc(OCc3ccc(C(F)(F)F)cc3)c(F)c2)no1

Standard InChI:  InChI=1S/C21H19F4N5O2.ClH/c22-15-10-13(18-28-19(32-29-18)16-2-1-9-30(16)20(26)27)5-8-17(15)31-11-12-3-6-14(7-4-12)21(23,24)25;/h3-8,10,16H,1-2,9,11H2,(H3,26,27);1H/t16-;/m0./s1

Standard InChI Key:  SPMABXSFRRPVSR-NTISSMGPSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   13.1411   -2.3814    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3327   -4.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3315   -5.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0396   -5.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7492   -5.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7464   -4.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0378   -4.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4526   -4.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1981   -4.4397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7426   -3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3314   -3.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5327   -3.2972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5557   -3.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9611   -4.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7598   -4.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8422   -3.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0944   -3.3023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9189   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5224   -1.9531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1400   -2.2570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6235   -5.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9161   -5.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2081   -5.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5014   -5.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7939   -5.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928   -6.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5052   -6.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2098   -6.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853   -6.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3774   -6.5647    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0858   -7.7901    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3732   -7.3754    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0394   -6.5691    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12  8  2  0
 13 10  1  1
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  3 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
  4 33  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: 449.41

Molecular Weight (Monoisotopic): 449.1475

AlogP: 4.50

#Rotatable Bonds: 5

Polar Surface Area: 101.26

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.15

CX LogP: 4.92

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -1.53

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