(S)-2-(6-(1-(8-fluoro-6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)quinolin-3-yloxy)ethanol

ID: ALA3414933

PubChem CID: 118732968

Max Phase: Preclinical

Molecular Formula: C23H20FN5O3

Molecular Weight: 433.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cc(F)c3nnc([C@@H](C)c4ccc5ncc(OCCO)cc5c4)n3c2)on1

Standard InChI:  InChI=1S/C23H20FN5O3/c1-13-7-21(32-28-13)17-10-19(24)23-27-26-22(29(23)12-17)14(2)15-3-4-20-16(8-15)9-18(11-25-20)31-6-5-30/h3-4,7-12,14,30H,5-6H2,1-2H3/t14-/m0/s1

Standard InChI Key:  XMYBKLSKESPOAJ-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -8.9787   -6.9311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0904   -5.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0298   -0.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3945   -4.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5577   -1.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4027   -6.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5007   -3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8272    0.3569    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9722   -4.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4975   -1.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5545   -0.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7986    1.0405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0118   -2.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3774   -7.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3319    0.7136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141   -2.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5325   -0.8904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 25  1  0
  4  1  1  0
 11  8  1  0
  2 21  2  0
  9 24  1  0
  3 13  1  0
 13 10  2  0
 26 17  2  0
 12 18  1  0
 17 14  1  0
 21 26  1  0
  6 20  1  0
  9 20  1  0
  6 16  1  0
 19  6  2  0
 14  3  2  0
  5 13  1  0
 15  2  1  0
  7  9  1  0
 24 12  2  0
 27  7  2  0
 10 22  1  0
 22 15  2  0
  7  5  1  0
  8 18  2  0
 12 19  1  0
 20 23  2  0
  1 11  2  0
 14 15  1  0
 23 27  1  0
 18  4  1  0
  5 28  1  6
 26 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3414933

   ---

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: 433.44

Molecular Weight (Monoisotopic): 433.1550

AlogP: 3.90

#Rotatable Bonds: 6

Polar Surface Area: 98.57

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.90

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -1.45

References

1. Peterson EA, Teffera Y, Albrecht BK, Bauer D, Bellon SF, Boezio A, Boezio C, Broome MA, Choquette D, Copeland KW, Dussault I, Lewis R, Lin MH, Lohman J, Liu J, Potashman M, Rex K, Shimanovich R, Whittington DA, Vaida KR, Harmange JC..  (2015)  Discovery of potent and selective 8-fluorotriazolopyridine c-Met inhibitors.,  58  (5): [PMID:25699405] [10.1021/jm501913a]

Source

Source(1):

• Scientific Literature