5-bromo-4-hydroxy-20-nitro-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: ALA376941

PubChem CID: 11845764

Max Phase: Preclinical

Molecular Formula: C20H20BrN3O6

Molecular Weight: 478.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCNC(=O)CCc2ccc(c([N+](=O)[O-])c2)Oc2cc(cc(Br)c2O)CCN1

Standard InChI:  InChI=1S/C20H20BrN3O6/c21-14-9-13-5-7-22-19(26)6-8-23-18(25)4-2-12-1-3-16(15(10-12)24(28)29)30-17(11-13)20(14)27/h1,3,9-11,27H,2,4-8H2,(H,22,26)(H,23,25)

Standard InChI Key:  SXUIRPYMJKUCAW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -2.6477  -16.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6487  -17.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9344  -17.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2186  -17.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212  -16.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9361  -15.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5034  -17.6295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2104  -17.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219  -17.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352  -17.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6344  -16.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9142  -15.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038  -16.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9100  -15.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1933  -14.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891  -13.9197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275  -13.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317  -12.6859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399  -13.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9564  -13.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6689  -13.9345    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646  -14.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769  -15.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480  -15.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3727  -16.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215  -18.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3502  -17.6274    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9325  -18.4611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2181  -18.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471  -18.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  1  2  2  0
 12 14  1  0
 28 29  2  0
 28 30  1  0
  3 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA376941

   5-Bromo-4-hydroxy-20-nitro-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: 478.30

Molecular Weight (Monoisotopic): 477.0535

AlogP: 2.97

#Rotatable Bonds: 1

Polar Surface Area: 130.80

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.06

CX Basic pKa: ┄

CX LogP: 2.55

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: 0.84

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