3-{5-Chloro-6-[(1R)-1-(5-fluoropyridin-2-yl)ethoxy]-1,2-benzoxazol-3-yl}propanoic Acid

ID: ALA4099913

PubChem CID: 121415041

Max Phase: Preclinical

Molecular Formula: C17H14ClFN2O4

Molecular Weight: 364.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](Oc1cc2onc(CCC(=O)O)c2cc1Cl)c1ccc(F)cn1

Standard InChI:  InChI=1S/C17H14ClFN2O4/c1-9(13-3-2-10(19)8-20-13)24-16-7-15-11(6-12(16)18)14(21-25-15)4-5-17(22)23/h2-3,6-9H,4-5H2,1H3,(H,22,23)/t9-/m1/s1

Standard InChI Key:  MPAKYDUYCIKGTK-SECBINFHSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.9775   -9.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7564   -8.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9587   -8.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4007  -10.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7753   -9.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6875   -6.5734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1765   -7.2371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7000   -7.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9119   -7.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9015   -6.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1967   -8.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4797   -7.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4735   -6.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1845   -6.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7564   -6.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0455   -6.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0516   -7.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3284   -6.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3181   -5.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6010   -5.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8901   -5.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8962   -6.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6134   -6.8730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1730   -5.2320    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7688   -8.0925    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 14  2  0
  9 11  2  0
 16 17  1  6
 15 16  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 21 24  1  0
 16 18  1  0
 13 15  1  0
 12 25  1  0
  3  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099913

   ---

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: 364.76

Molecular Weight (Monoisotopic): 364.0626

AlogP: 4.17

#Rotatable Bonds: 6

Polar Surface Area: 85.45

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.98

CX Basic pKa: 1.24

CX LogP: 3.06

CX LogD: -0.11

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -1.02

References

1. Walker AL, Ancellin N, Beaufils B, Bergeal M, Binnie M, Bouillot A, Clapham D, Denis A, Haslam CP, Holmes DS, Hutchinson JP, Liddle J, McBride A, Mirguet O, Mowat CG, Rowland P, Tiberghien N, Trottet L, Uings I, Webster SP, Zheng X, Mole DJ..  (2017)  Development of a Series of Kynurenine 3-Monooxygenase Inhibitors Leading to a Clinical Candidate for the Treatment of Acute Pancreatitis.,  60  (8): [PMID:28398044] [10.1021/acs.jmedchem.7b00055]

Source

Source(1):

• Scientific Literature