8,10-Dibromo-4-hydroxy-9-methoxy-1,6-dioxa-2-aza-spiro[4.6]undeca-2,7,9-triene-3-carboxylic acid {2-[4-(2-amino-1-hydroxy-ethyl)-2,6-dibromo-phenoxy]-ethyl}-amide

ID: ALA2367685

PubChem CID: 49766996

Max Phase: Preclinical

Molecular Formula: C20H21Br4N3O7

Molecular Weight: 735.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=C(Br)C[C@]2(OC=C1Br)ON=C(C(=O)NCCOc1c(Br)cc(C(O)CN)cc1Br)[C@@H]2O

Standard InChI:  InChI=1S/C20H21Br4N3O7/c1-31-16-12(23)6-20(33-8-13(16)24)18(29)15(27-34-20)19(30)26-2-3-32-17-10(21)4-9(5-11(17)22)14(28)7-25/h4-5,8,14,18,28-29H,2-3,6-7,25H2,1H3,(H,26,30)/t14?,18-,20-/m0/s1

Standard InChI Key:  UAXHDVNKHYRWNX-ZACQIXQRSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  1  0  0  0  0  0999 V2000
    2.9008   -0.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759   -2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8261   -1.8422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049   -1.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7380    0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131   -0.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6005   -0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7136   -1.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882    0.9378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -0.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300   -3.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3768   -4.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2268   -4.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1437   -3.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6272   -5.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7772   -4.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8520   -5.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1506   -3.2926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8002   -0.4543    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6880   -1.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -3.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674    1.7588    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.0753    1.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2566   -5.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2896   -2.9676    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.4433   -5.1432    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.7433   -3.5260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3396   -6.7436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0318   -5.3807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1148   -6.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3387   -3.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9639   -3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1628    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  8  1  0
  1  4  1  0
  5  7  2  0
  1  6  1  6
  7  6  1  0
  8  1  1  0
  9 13  2  0
  1 10  1  1
 11  2  1  0
 12 28  1  0
 13 10  1  0
 14 12  2  0
 15 12  1  0
 16 17  1  0
 17 15  2  0
 18 14  1  0
 19 11  2  0
 20  7  1  0
  4 21  1  6
 22 11  1  0
 23  9  1  0
 24  5  1  0
 25 16  1  0
 26 15  1  0
 27 14  1  0
 28 33  1  0
 29 31  1  0
 30 25  1  0
 31 25  1  0
 32 22  1  0
 33 32  1  0
 34 24  1  0
  2  3  2  0
  9  5  1  0
 18 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2367685

   (1S,5S)-N-[2-[4-(2-amino-1-hydroxy-ethyl)-2,6-dibromo-phenoxy]ethyl]-7,9-dibromo-1-hydroxy-8-methoxy-4,11-dioxa-3-azaspiro[4.6]undeca-2,7,9-triene-2-carboxamide

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: 735.02

Molecular Weight (Monoisotopic): 730.8113

AlogP: 3.05

#Rotatable Bonds: 8

Polar Surface Area: 144.86

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.52

CX Basic pKa: 9.12

CX LogP: 2.45

CX LogD: 0.75

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: 1.69

References

1. Nicholas GM, Eckman LL, Ray S, Hughes RO, Pfefferkorn JA, Barluenga S, Nicolaou KC, Bewley CA..  (2002)  Bromotyrosine-derived natural and synthetic products as inhibitors of mycothiol-S-conjugate amidase.,  12  (17): [PMID:12161164] [10.1016/s0960-894x(02)00385-2]

Source

Source(1):

• Scientific Literature