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-ethyl)-2,6-dibromo-phenoxy]-ethyl}-amide

ID: ALA2367683

PubChem CID: 49766995

Max Phase: Preclinical

Molecular Formula: C20H21Br4N3O6

Molecular Weight: 719.02

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H21Br4N3O6/c1-30-16-13(23)8-20(32-9-14(16)24)18(28)15(27-33-20)19(29)26-4-5-31-17-11(21)6-10(2-3-25)7-12(17)22/h6-7,9,18,28H,2-5,8,25H2,1H3,(H,26,29)/t18-,20-/m0/s1

Standard InChI Key:  HXZJJMWWLXYLEN-ICSRJNTNSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
    3.6052   -0.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7803   -2.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5305   -1.6547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2134   -1.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4424    0.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8175   -0.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3049   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4180   -0.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1926    1.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387   -0.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -2.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0812   -3.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9553    0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9312   -4.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8522   -3.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4816   -4.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5564   -5.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8550   -3.1051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3316   -4.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5046   -0.2668    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.3924   -1.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679   -3.3635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759    1.9464    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7797    1.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9940   -2.7800    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.1518   -4.9556    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -3.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0440   -6.5561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9651   -5.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0431   -3.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8192   -6.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6683   -3.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672    2.0464    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 27  1  0
 13 10  1  0
 14 12  2  0
 15 12  1  0
 16 15  2  0
 17 14  1  0
 18 11  2  0
 19 16  1  0
 20  7  1  0
  4 21  1  6
 22 11  1  0
 23  9  1  0
 24  5  1  0
 25 15  1  0
 26 14  1  0
 27 32  1  0
 28 31  1  0
 29 19  1  0
 30 22  1  0
 31 29  1  0
 32 30  1  0
 33 24  1  0
  2  3  2  0
  9  5  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2367683

   (1S,5S)-N-[2-[4-(2-aminoethyl)-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: 719.02

Molecular Weight (Monoisotopic): 714.8164

AlogP: 3.56

#Rotatable Bonds: 8

Polar Surface Area: 124.63

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.54

CX Basic pKa: 9.77

CX LogP: 3.24

CX LogD: 1.08

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.35

Np Likeness Score: 1.64

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