21-amino-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: ALA212154

PubChem CID: 11845228

Max Phase: Preclinical

Molecular Formula: C20H22BrN3O4

Molecular Weight: 448.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H22BrN3O4/c21-14-9-13-5-7-23-19(26)6-8-24-18(25)4-2-12-1-3-16(15(22)10-12)28-17(11-13)20(14)27/h1,3,9-11,27H,2,4-8,22H2,(H,23,26)(H,24,25)

Standard InChI Key:  GGXMZDGJOAHEGN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.7777  -17.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7766  -18.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4909  -18.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068  -18.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2041  -17.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4892  -16.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9220  -18.5051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6357  -18.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3472  -18.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0606  -18.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0597  -17.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3395  -16.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6291  -17.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3353  -16.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6186  -15.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6144  -14.7953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8978  -14.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8936  -13.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1854  -14.8027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4689  -14.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565  -14.8101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7607  -15.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484  -16.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774  -16.0439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0527  -16.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3469  -19.3293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7755  -18.5030    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.4907  -19.3321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA212154

   20-Amino-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: 448.32

Molecular Weight (Monoisotopic): 447.0794

AlogP: 2.64

#Rotatable Bonds: ┄

Polar Surface Area: 113.68

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.10

CX Basic pKa: 2.78

CX LogP: 1.78

CX LogD: 1.31

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 1.18

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