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

ID: ALA378025

PubChem CID: 11845227

Max Phase: Preclinical

Molecular Formula: C17H15BrINO3

Molecular Weight: 488.12

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H15BrINO3/c18-12-7-11-5-6-20-16(21)4-2-10-1-3-14(13(19)8-10)23-15(9-11)17(12)22/h1,3,7-9,22H,2,4-6H2,(H,20,21)

Standard InChI Key:  BSGKEDZPZSXTTA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.5286   -7.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6433   -8.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4073   -9.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0754   -8.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9733   -7.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1966   -7.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5685   -9.8074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1966   -6.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8861   -6.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6462   -6.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2274   -5.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3581   -9.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7678  -10.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5912  -10.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0087   -9.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5852   -9.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7461   -9.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9905   -8.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9385   -7.3454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7866   -7.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0018   -9.2484    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   14.3572  -11.3255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0012  -11.3258    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  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
  2 21  1  0
  2  3  1  0
 13 22  1  0
  3  4  2  0
 14 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA378025

   5-Bromo-4-hydroxy-16-iodo-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: 488.12

Molecular Weight (Monoisotopic): 486.9280

AlogP: 4.16

#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: 4.41

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: 1.25

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