(+/-)-5,17-dibromo-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: ALA386905

PubChem CID: 11845762

Max Phase: Preclinical

Molecular Formula: C17H15Br2NO3

Molecular Weight: 441.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCc2ccc(c(Br)c2)Oc2cc(cc(Br)c2O)CCN1

Standard InChI:  InChI=1S/C17H15Br2NO3/c18-12-7-10-1-3-14(12)23-15-9-11(8-13(19)17(15)22)5-6-20-16(21)4-2-10/h1,3,7-9,22H,2,4-6H2,(H,20,21)

Standard InChI Key:  JGORQZKQHPVGIP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -4.5659  -14.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849  -15.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608  -15.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125  -14.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2990  -13.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259  -13.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5149  -13.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854  -12.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136  -12.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875  -12.2407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304  -11.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837  -12.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576  -12.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9810  -16.1141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6302  -16.0386    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8490  -13.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2639  -14.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561  -15.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0348  -15.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3768  -14.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334  -13.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3775  -15.8013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2029  -14.3700    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 10 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
  3 14  1  0
  6  7  1  0
  2 15  1  0
  3  4  2  0
 13 16  1  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
 21 16  1  0
 14 18  1  0
  2  3  1  0
 19 22  1  0
  9 11  2  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA386905

   5,16-Dibromo-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: 441.12

Molecular Weight (Monoisotopic): 438.9419

AlogP: 4.31

#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: 7.10

CX Basic pKa: ┄

CX LogP: 4.25

CX LogD: 3.77

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 1.58

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]

2. Zieminska E, Lazarewicz JW, Couladouros EA, Moutsos VI, Pitsinos EN..  (2008)  Open-chain half-bastadins mimic the effects of cyclic bastadins on calcium homeostasis in cultured neurons.,  18  (21): [PMID:18851910] [10.1016/j.bmcl.2008.09.080]

Source

Source(1):

• Scientific Literature