3-Benzo[1,3]dioxol-5-yl-4-[3-(2-bromoethoxy)-4,5-dimethoxybenzyl]-5-hydroxy-5-(4-methoxyphenyl)-5H-furan-2-one

ID: ALA594265

PubChem CID: 46228086

Max Phase: Preclinical

Molecular Formula: C29H27BrO9

Molecular Weight: 599.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2(O)OC(=O)C(c3ccc4c(c3)OCO4)=C2Cc2cc(OC)c(OC)c(OCCBr)c2)cc1

Standard InChI:  InChI=1S/C29H27BrO9/c1-33-20-7-5-19(6-8-20)29(32)21(12-17-13-24(34-2)27(35-3)25(14-17)36-11-10-30)26(28(31)39-29)18-4-9-22-23(15-18)38-16-37-22/h4-9,13-15,32H,10-12,16H2,1-3H3

Standard InChI Key:  GEKSWALNDXSWLV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
    9.4096   -2.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917   -2.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1879   -1.5863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4002   -1.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9232   -2.0063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1593   -3.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6100   -0.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6820   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6856   -0.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9682    0.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2481   -0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -0.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9679   -1.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5343    0.3242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5341    1.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9068   -1.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9171   -0.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6395    0.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6503    0.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9413    1.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2201    0.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2129    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9052   -2.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9114   -3.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6280   -4.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6115   -2.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3286   -2.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3390   -3.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1295   -3.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6077   -3.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1127   -2.5312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9506    2.1085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5102    1.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5177    2.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2417    2.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3693    1.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0775    0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7965    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5047    0.8253    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  2  0
 22 17  1  0
 10 11  2  0
  1  2  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
 25 28  2  0
  1  6  2  0
 27 26  2  0
 26 23  1  0
  2 23  1  0
 27 28  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
  4  7  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 14 15  1  0
 20 32  1  0
  2  3  2  0
 21 33  1  0
  3 16  1  0
 33 34  1  0
  4  8  1  0
 32 35  1  0
 16 17  1  0
 19 36  1  0
  3  4  1  0
 36 37  1  0
 17 18  2  0
 37 38  1  0
  8  9  2  0
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA594265

   3-Benzo[1,3]dioxol-5-yl-4-[3-(2-bromoethoxy)-4,5-dimethoxybenzyl]-5-hydroxy-5-(4-methoxyphenyl)-5H-furan-2-one

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: 599.43

Molecular Weight (Monoisotopic): 598.0838

AlogP: 4.61

#Rotatable Bonds: 10

Polar Surface Area: 101.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.56

CX Basic pKa: ┄

CX LogP: 5.46

CX LogD: 5.46

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.26

Np Likeness Score: 0.45

References

1. Höltke C, Law MP, Wagner S, Kopka K, Faust A, Breyholz HJ, Schober O, Bremer C, Riemann B, Schäfers M..  (2009)  PET-compatible endothelin receptor radioligands: synthesis and first in vitro and in vivo studies.,  17  (20): [PMID:19766010] [10.1016/j.bmc.2009.08.058]

Source

Source(1):

• Scientific Literature