1-(2'-Bromo-3'-hydroxy-3'-methylbutyl)-6-bromo-7-methoxymukonal

ID: ALA1818863

PubChem CID: 54577839

Max Phase: Preclinical

Molecular Formula: C19H19Br2NO4

Molecular Weight: 485.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2[nH]c3c(CC(Br)C(C)(C)O)c(O)c(C=O)cc3c2cc1Br

Standard InChI:  InChI=1S/C19H19Br2NO4/c1-19(2,25)16(21)6-12-17-11(4-9(8-23)18(12)24)10-5-13(20)15(26-3)7-14(10)22-17/h4-5,7-8,16,22,24-25H,6H2,1-3H3

Standard InChI Key:  APDFFKOKRGUFJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    9.3634  -23.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6508  -23.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6498  -23.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7764  -20.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4931  -20.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0243  -21.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5865  -19.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1195  -20.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8378  -21.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4898  -21.7899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9455  -20.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1734  -21.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9714  -21.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5423  -20.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3098  -20.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5122  -19.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2453  -19.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5265  -18.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6806  -20.9422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7449  -22.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9330  -22.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8415  -23.2759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4016  -21.7221    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.3437  -21.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5742  -21.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8792  -19.5371    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  8  7  2  0
 13 14  2  0
  7  4  1  0
 14 15  1  0
  8  9  1  0
 15 16  2  0
 16 11  1  0
  2  1  1  0
  4 17  1  0
  4  5  2  0
 17 18  2  0
  3  2  1  0
  5 19  1  0
  9 10  1  0
  6 20  1  0
 10 12  1  0
 20 21  1  0
 21  2  1  0
 11  8  1  0
  2 22  1  0
  5  6  1  0
 21 23  1  0
  6  9  2  0
 14 24  1  0
 11 12  2  0
 24 25  1  0
 15 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1818863

   6-bromo-1-(2-bromo-3-hydroxy-3-methylbutyl)-2-hydroxy-7-methoxy-9H-carbazole-3-carbaldehyde

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: 485.17

Molecular Weight (Monoisotopic): 482.9681

AlogP: 4.69

#Rotatable Bonds: 5

Polar Surface Area: 82.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.19

CX Basic pKa: ┄

CX LogP: 4.89

CX LogD: 4.82

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: 0.96

References

1. Thongthoom T, Promsuwan P, Yenjai C..  (2011)  Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series.,  46  (9): [PMID:21641693] [10.1016/j.ejmech.2011.05.041]

Source

Source(1):

• Scientific Literature