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

ID: ALA386432

PubChem CID: 11845761

Max Phase: Preclinical

Molecular Formula: C17H15BrN2O5

Molecular Weight: 407.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCc2ccc(c([N+](=O)[O-])c2)Oc2cc(cc(Br)c2O)CCN1

Standard InChI:  InChI=1S/C17H15BrN2O5/c18-12-7-11-5-6-19-16(21)4-2-10-1-3-14(13(8-10)20(23)24)25-15(9-11)17(12)22/h1,3,7-9,22H,2,4-6H2,(H,19,21)

Standard InChI Key:  QXKBFCFPQCDZHM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -3.3515    0.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2366   -0.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4723   -0.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9059    0.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110   -1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831    2.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9932    2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327    2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6512    2.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209   -1.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2871   -1.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1306   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931   -0.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1328   -0.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1124    0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403    1.3760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916    1.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8812   -0.5242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7594   -1.3358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448   -0.2238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5218   -2.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1231   -2.6068    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  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  3  1  0
  3  4  2  0
 21 22  2  0
 21 23  1  0
  2 21  1  0
  4  5  1  0
 13 24  1  0
  5  6  2  0
 14 25  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA386432

   5-Bromo-4-hydroxy-16-nitro-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: 407.22

Molecular Weight (Monoisotopic): 406.0164

AlogP: 3.46

#Rotatable Bonds: 1

Polar Surface Area: 101.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.06

CX Basic pKa: ┄

CX LogP: 3.42

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: 0.94

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