US8604061, 82 (S,R)

ID: ALA3684920

PubChem CID: 59323844

Max Phase: Preclinical

Molecular Formula: C12H16N2O

Molecular Weight: 204.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](C[C@H]1COC(N)=N1)c1ccccc1

Standard InChI:  InChI=1S/C12H16N2O/c1-9(10-5-3-2-4-6-10)7-11-8-15-12(13)14-11/h2-6,9,11H,7-8H2,1H3,(H2,13,14)/t9-,11+/m1/s1

Standard InChI Key:  AGHKCLYLZRRYHN-KOLCDFICSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  1  0  0  0  0  0999 V2000
    2.5958   -2.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -1.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5513   -0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5512   -2.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7967   -3.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306   -2.9878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2811   -4.4026    0.0000 N   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
   -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
  2  1  1  1
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  7  9  1  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3684920

   (4S)-4-[(2R)-2-phenylpropyl]-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: 204.27

Molecular Weight (Monoisotopic): 204.1263

AlogP: 1.89

#Rotatable Bonds: 3

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: 7.40

CX LogP: 2.48

CX LogD: 2.19

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.82

Np Likeness Score: 0.22

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