(+/-)-5,15,17-tribromo-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: ALA380242

PubChem CID: 11845062

Max Phase: Preclinical

Molecular Formula: C17H14Br3NO3

Molecular Weight: 520.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCc2cc(Br)c(cc2Br)Oc2cc(cc(Br)c2O)CCN1

Standard InChI:  InChI=1S/C17H14Br3NO3/c18-11-8-14-12(19)7-10(11)1-2-16(22)21-4-3-9-5-13(20)17(23)15(6-9)24-14/h5-8,23H,1-4H2,(H,21,22)

Standard InChI Key:  FZPRZWMNCDTIIJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.8383   -8.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -9.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7175  -10.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859   -9.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838   -8.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -8.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8788  -10.8537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067   -7.6586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1965   -7.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9570   -7.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5385   -7.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6688  -10.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0787  -11.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9025  -11.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3202  -10.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965  -10.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0569  -10.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3020   -9.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2494   -8.3905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0980   -8.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112  -10.2944    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.7166   -8.2966    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6679  -12.3726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3127  -12.3729    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  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
  2 21  1  0
  2  3  1  0
  5 22  1  0
  3  4  2  0
 13 23  1  0
  4  5  1  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA380242

   5,15,17-Tribromo-4-hydroxy-2-oxa-10-azatricyclo[12.2.2.13,7]nonadeca-1(17),3,5,7(19),14(18),15-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: 520.01

Molecular Weight (Monoisotopic): 516.8524

AlogP: 5.08

#Rotatable Bonds: ┄

Polar Surface Area: 58.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.10

CX Basic pKa: ┄

CX LogP: 5.02

CX LogD: 4.54

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: 1.13

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