(S)-5-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)thiophene-2-carbonitrile

ID: ALA4294481

PubChem CID: 145993942

Max Phase: Preclinical

Molecular Formula: C18H11Cl2FN2OS

Molecular Weight: 393.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Oc1cncc(-c2ccc(C#N)s2)c1)c1c(Cl)ccc(F)c1Cl

Standard InChI:  InChI=1S/C18H11Cl2FN2OS/c1-10(17-14(19)3-4-15(21)18(17)20)24-12-6-11(8-23-9-12)16-5-2-13(7-22)25-16/h2-6,8-10H,1H3/t10-/m0/s1

Standard InChI Key:  AKJLHSCLNWWZQR-JTQLQIEISA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   13.5978  -14.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5967  -15.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3047  -16.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0144  -15.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0115  -14.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3029  -14.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3005  -13.5535    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7177  -14.3647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3045  -16.8253    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.7227  -16.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4298  -15.5964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1381  -16.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1348  -16.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8423  -17.2269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5503  -16.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5464  -15.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8383  -15.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7240  -16.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2508  -15.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9990  -15.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5427  -15.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1305  -14.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3321  -14.7660    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.4579  -13.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7864  -13.0953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  5  8  1  0
  3  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 18  1  1
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
 16 19  1  0
 24 25  3  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4294481

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 393.27

Molecular Weight (Monoisotopic): 391.9953

AlogP: 6.27

#Rotatable Bonds: 4

Polar Surface Area: 45.91

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.07

CX LogP: 5.50

CX LogD: 5.50

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.49

Np Likeness Score: -1.21

References

1. Lim JW, Kim SK, Choi SY, Kim DH, Gadhe CG, Lee HN, Kim HJ, Kim J, Cho SJ, Hwang H, Seong J, Jeong KS, Lee JY, Lim SM, Lee JW, Pae AN..  (2018)  Identification of crizotinib derivatives as potent SHIP2 inhibitors for the treatment of Alzheimer's disease.,  157  [PMID:30103190] [10.1016/j.ejmech.2018.07.071]

Source

Source(1):

• Scientific Literature