(+/-)-17-amino-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: ALA213687

PubChem CID: 11845060

Max Phase: Preclinical

Molecular Formula: C17H17BrN2O3

Molecular Weight: 377.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cc2ccc1Oc1cc(cc(Br)c1O)CCNC(=O)CC2

Standard InChI:  InChI=1S/C17H17BrN2O3/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,2,4-6,19H2,(H,20,21)

Standard InChI Key:  FRZBSKDYTIMNOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    1.8582    0.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9730   -0.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370   -0.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051   -0.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262    0.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -1.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262    1.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158    1.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9760    1.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5572    2.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6879   -1.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0976   -2.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9211   -2.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387   -1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151   -1.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759   -1.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3205   -0.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683    0.8065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1166    0.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3313   -1.0966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -3.1740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3312   -3.1742    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:

   

   ALA213687

   16-Amino-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: 377.24

Molecular Weight (Monoisotopic): 376.0423

AlogP: 3.13

#Rotatable Bonds: ┄

Polar Surface Area: 84.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.10

CX Basic pKa: 2.72

CX LogP: 2.65

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: 1.36

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