21-azido-4-hydroxy-5-bromo-2-oxa-10,14-diaza-tricyclo-[16.2.2.10,0]tricosa-1(21),3(23),4,6,18(22),19-hexaene-11,15-dione

ID: ALA209427

PubChem CID: 11845946

Max Phase: Preclinical

Molecular Formula: C20H20BrN5O4

Molecular Weight: 474.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=Nc1cc2ccc1Oc1cc(cc(Br)c1O)CCNC(=O)CCNC(=O)CC2

Standard InChI:  InChI=1S/C20H20BrN5O4/c21-14-9-13-5-7-23-19(28)6-8-24-18(27)4-2-12-1-3-16(15(10-12)25-26-22)30-17(11-13)20(14)29/h1,3,9-11,29H,2,4-8H2,(H,23,28)(H,24,27)

Standard InChI Key:  YQWNAKYARKZIHD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    9.2893   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2882   -3.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -3.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7184   -3.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7157   -2.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0009   -2.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4335   -3.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1474   -3.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8588   -3.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5721   -3.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5712   -2.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8511   -2.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1407   -2.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8468   -1.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1303   -0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1260    0.0262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4094    0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4051    1.2600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6971    0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9805    0.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2681    0.0115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2724   -0.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5600   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9890   -1.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5643   -2.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8584   -4.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2871   -3.6814    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.0024   -4.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9958   -5.3333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -6.1583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  4  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
 17 18  2  0
  8  9  2  0
 17 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  2  0
 22 23  1  0
  5  6  2  0
 22 24  2  0
  1 25  1  0
 11 12  1  0
 23 25  1  0
  6  1  1  0
  9 26  1  0
 12 13  2  0
 10 27  1  0
 13  8  1  0
  3 28  1  0
 28 29  2  0
  1  2  2  0
 29 30  2  0
M  CHG  2  29   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA209427

   20-Azido-5-bromo-4-hydroxy-2-oxa-10,14-diazatricyclo[16.2.2.13,7]tricosa-1(20),3,5,7(23),18,21-hexaene-11,15-dione

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: 474.32

Molecular Weight (Monoisotopic): 473.0699

AlogP: 4.00

#Rotatable Bonds: 1

Polar Surface Area: 136.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.09

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: 1.06

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