US8604061, 369

ID: ALA3684915

PubChem CID: 59323783

Max Phase: Preclinical

Molecular Formula: C12H13ClN2O

Molecular Weight: 236.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC1=N[C@@H](c2ccc(Cl)cc2C2CC2)CO1

Standard InChI:  InChI=1S/C12H13ClN2O/c13-8-3-4-9(10(5-8)7-1-2-7)11-6-16-12(14)15-11/h3-5,7,11H,1-2,6H2,(H2,14,15)/t11-/m1/s1

Standard InChI Key:  OHEHXHSMXPWYQM-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 16 18  0  0  1  0  0  0  0  0999 V2000
    6.1467   -1.8743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481   -4.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519   -4.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  4  7  1  6
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13  7  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3684915

   (4S)-4-(4-chloro-2-cyclopropylphenyl)-4,5-dihydro-1,3-oxazol-2-amine

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: 236.70

Molecular Weight (Monoisotopic): 236.0716

AlogP: 2.60

#Rotatable Bonds: 2

Polar Surface Area: 47.61

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.74

CX LogP: 2.85

CX LogD: 2.76

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.86

Np Likeness Score: 0.01

References

1.  (2013)  2-aminooxazolines as TAAR1 ligands, 

2. Galley G, Beurier A, Décoret G, Goergler A, Hutter R, Mohr S, Pähler A, Schmid P, Türck D, Unger R, Zbinden KG, Hoener MC, Norcross RD..  (2016)  Discovery and Characterization of 2-Aminooxazolines as Highly Potent, Selective, and Orally Active TAAR1 Agonists.,  7  (2): [PMID:26985297] [10.1021/acsmedchemlett.5b00449]

Source

Source(2):

• Scientific Literature
• BindingDB Database