(+/-)-5-bromo-4-hydroxy-2-oxa-10-aza-tricyclo[12.2.2.10,0]nonadeca-1(17),3(19),4,6,14(18),15-hexaen-11-one

ID: ALA210076

PubChem CID: 11845763

Max Phase: Preclinical

Molecular Formula: C17H16BrNO3

Molecular Weight: 362.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCc2ccc(cc2)Oc2cc(cc(Br)c2O)CCN1

Standard InChI:  InChI=1S/C17H16BrNO3/c18-14-9-12-7-8-19-16(20)6-3-11-1-4-13(5-2-11)22-15(10-12)17(14)21/h1-2,4-5,9-10,21H,3,6-8H2,(H,19,20)

Standard InChI Key:  ZDPNXGGQOSNLLU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.8794   -8.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9941   -9.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7577  -10.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4256   -9.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3236   -8.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5471   -8.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9189  -10.8136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5471   -7.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2363   -7.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9963   -7.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5772   -6.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7083  -10.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1178  -11.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9410  -11.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3584  -10.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9349  -10.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0962  -10.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402   -9.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2884   -8.3524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1364   -8.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7073  -12.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3509  -12.3316    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 19  1  0
 10 11  2  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
 18 20  1  0
 19 20  1  0
  1  2  2  0
 13 21  1  0
  2  3  1  0
 14 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA210076

   5-Bromo-4-hydroxy-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-1(16),3,5,7(19),14,17-hexaen-11-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: 362.22

Molecular Weight (Monoisotopic): 361.0314

AlogP: 3.55

#Rotatable Bonds: ┄

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.11

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 3.02

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.75

Np Likeness Score: 2.02

References

1. Masuno MN, Pessah IN, Olmstead MM, Molinski TF..  (2006)  Simplified cyclic analogues of bastadin-5. Structure-activity relationships for modulation of the RyR1/FKBP12 Ca2+ channel complex.,  49  (15): [PMID:16854055] [10.1021/jm050708u]

Source

Source(1):

• Scientific Literature