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

ID: ALA2331788

PubChem CID: 71720623

Max Phase: Preclinical

Molecular Formula: C14H15IN2O2

Molecular Weight: 370.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1c2c(on1Cc1ccc(I)cc1)CCNCC2

Standard InChI:  InChI=1S/C14H15IN2O2/c15-11-3-1-10(2-4-11)9-17-14(18)12-5-7-16-8-6-13(12)19-17/h1-4,16H,5-9H2

Standard InChI Key:  FKXIIGYVOKUNNO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    6.4566   -2.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558   -2.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0945   -3.1944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4438   -3.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2445   -4.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8926   -3.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6690   -3.8754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1470   -3.2145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6700   -2.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9230   -1.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9683   -3.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3764   -3.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650   -4.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3724   -5.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1905   -5.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5994   -4.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1896   -3.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5996   -6.0438    0.0000 I   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
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2331788

   2-[(4-iodophenyl)methyl]-5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one

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: 370.19

Molecular Weight (Monoisotopic): 370.0178

AlogP: 1.78

#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: 1.98

CX LogD: -0.20

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: -0.57

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