2-benzyl-5,6,7,8-tetrahydro-2H-isoxazolo[4,5-d]azepin-3(4H)-one

ID: ALA2331807

PubChem CID: 14515725

Max Phase: Preclinical

Molecular Formula: C14H16N2O2

Molecular Weight: 244.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2c(on1Cc1ccccc1)CCNCC2

Standard InChI:  InChI=1S/C14H16N2O2/c17-14-12-6-8-15-9-7-13(12)18-16(14)10-11-4-2-1-3-5-11/h1-5,15H,6-10H2

Standard InChI Key:  BWAFYEDXZXBSIK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   17.6579   -0.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4530   -0.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2958   -1.4280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6451   -2.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4417   -2.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0862   -1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0856   -1.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8579   -2.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3359   -1.4480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8589   -0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1119   -0.0136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1531   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5612   -2.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1498   -2.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5572   -3.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3753   -3.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7842   -2.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3744   -2.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  1  0
  1  3  1  0
  3  4  1  0
  7  5  1  0
  4  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
 10 11  2  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2331807

   N-Bn-THAZ Fumarate

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: 244.29

Molecular Weight (Monoisotopic): 244.1212

AlogP: 1.18

#Rotatable Bonds: 2

Polar Surface Area: 47.17

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.62

CX LogP: 1.05

CX LogD: -1.13

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -0.19

References

1. Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, Stensbøl TB, Gloriam DE, Krogsgaard-Larsen P, Frølund B..  (2013)  Design, synthesis, and pharmacological characterization of N- and O-substituted 5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol analogues: novel 5-HT(2A)/5-HT(2C) receptor agonists with pro-cognitive properties.,  56  (3): [PMID:23301527] [10.1021/jm301656h]

Source

Source(1):

• Scientific Literature