3-{5-Chloro-6-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-benzoxazol-3-yl}propanoic Acid tris(hydroxymethyl)aminomethane salt

ID: ALA4100868

PubChem CID: 137658639

Max Phase: Preclinical

Molecular Formula: C21H26ClN3O7

Molecular Weight: 346.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](Oc1cc2onc(CCC(=O)O)c2cc1Cl)c1ccccn1.NC(CO)(CO)CO

Standard InChI:  InChI=1S/C17H15ClN2O4.C4H11NO3/c1-10(13-4-2-3-7-19-13)23-16-9-15-11(8-12(16)18)14(20-24-15)5-6-17(21)22;5-4(1-6,2-7)3-8/h2-4,7-10H,5-6H2,1H3,(H,21,22);6-8H,1-3,5H2/t10-;/m1./s1

Standard InChI Key:  UGOODDFAPJBOMS-HNCPQSOCSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    6.4928   -6.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -7.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9054   -7.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0904   -7.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3813   -6.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722   -7.1120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3180   -7.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0802   -5.6937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8308   -7.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6163   -7.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8162   -6.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2495   -8.4169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0416   -5.3738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5599   -6.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0600   -6.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3424   -5.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3429   -4.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0570   -4.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6252   -4.5555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9153   -4.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9148   -5.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1978   -4.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1941   -3.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4806   -3.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7665   -3.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7702   -4.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4837   -4.9774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6325   -6.2055    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  2  4  1  0
  5  6  1  0
  2  5  1  0
  3  7  1  0
  1  8  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
  9 13  1  0
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 14 18  1  0
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 20 21  2  0
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 17 19  2  0
 24 25  1  6
 23 24  1  0
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 29 30  2  0
 30 31  1  0
 26 31  2  0
 24 26  1  0
 21 23  1  0
 20 32  1  0
 11 16  1  0
M  END

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: 346.77

Molecular Weight (Monoisotopic): 346.0720

AlogP: 4.03

#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: 4.16

CX Basic pKa: 3.51

CX LogP: 2.45

CX LogD: -0.25

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -1.11

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