2-amino-2-(hydroxymethyl)propane-1,3-diol 3-(5-chloro-6-cyclopropoxy-2-oxobenzo[d]oxazol-3(2H)-yl)propanoate

ID: ALA4096688

PubChem CID: 118174652

Max Phase: Preclinical

Molecular Formula: C17H23ClN2O8

Molecular Weight: 297.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CO)(CO)CO.O=C(O)CCn1c(=O)oc2cc(OC3CC3)c(Cl)cc21

Standard InChI:  InChI=1S/C13H12ClNO5.C4H11NO3/c14-8-5-9-11(6-10(8)19-7-1-2-7)20-13(18)15(9)4-3-12(16)17;5-4(1-6,2-7)3-8/h5-7H,1-4H2,(H,16,17);6-8H,1-3,5H2

Standard InChI Key:  RQMAHFJBTNTDNN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   33.1803   -3.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8881   -3.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5958   -3.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8881   -2.4048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.3036   -3.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4725   -3.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8820   -4.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5866   -4.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0385   -2.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0374   -2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7522   -3.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7503   -1.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4658   -2.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4707   -2.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2582   -3.1906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7402   -2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2504   -1.8532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5652   -2.5141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3224   -3.3562    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.5177   -3.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3258   -4.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5852   -4.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3934   -5.0906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0368   -5.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3238   -1.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6094   -2.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7875   -2.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2004   -2.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
  1  6  1  0
  2  7  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 16 18  2  0
 10 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
  9 25  1  0
 25 26  1  0
 27 26  1  0
 28 27  1  0
 26 28  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: 297.69

Molecular Weight (Monoisotopic): 297.0404

AlogP: 2.26

#Rotatable Bonds: 5

Polar Surface Area: 81.67

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.17

CX Basic pKa: ┄

CX LogP: 1.82

CX LogD: -1.63

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.92

Np Likeness Score: -0.69

References

1. Liddle J, Beaufils B, Binnie M, Bouillot A, Denis AA, Hann MM, Haslam CP, Holmes DS, Hutchinson JP, Kranz M, McBride A, Mirguet O, Mole DJ, Mowat CG, Pal S, Rowland P, Trottet L, Uings IJ, Walker AL, Webster SP..  (2017)  The discovery of potent and selective kynurenine 3-monooxygenase inhibitors for the treatment of acute pancreatitis.,  27  (9): [PMID:28336141] [10.1016/j.bmcl.2017.02.078]

2. 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