(Z)-2-[N-(3-Bromobenzyl)-5-methoxyindol-3-ylmethylene]-4,6-dihydroxybenzofuran-3(2H)-one

ID: ALA3964042

PubChem CID: 134150848

Max Phase: Preclinical

Molecular Formula: C25H18BrNO5

Molecular Weight: 492.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(/C=C1\Oc3cc(O)cc(O)c3C1=O)cn2Cc1cccc(Br)c1

Standard InChI:  InChI=1S/C25H18BrNO5/c1-31-18-5-6-20-19(11-18)15(13-27(20)12-14-3-2-4-16(26)7-14)8-23-25(30)24-21(29)9-17(28)10-22(24)32-23/h2-11,13,28-29H,12H2,1H3/b23-8-

Standard InChI Key:  SIMSFCJSWMVLNH-NYAPKIOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    2.2069  -14.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2058  -15.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205  -15.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187  -13.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341  -14.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6390  -15.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308  -15.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155  -14.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229  -14.0598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923  -13.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9196  -16.3901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6903  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404  -14.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2276  -14.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6463  -12.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9775  -13.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3115  -13.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0519  -14.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5985  -14.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4049  -14.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6617  -13.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1134  -13.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6495  -11.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9548  -15.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6970  -15.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366  -11.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9409  -10.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321  -10.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5137  -10.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5085  -11.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2219  -11.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7910  -11.9455    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  1 10  1  0
  3 11  1  0
  7 12  2  0
  8 13  2  0
 13 14  1  0
 14 18  1  0
 17 15  1  0
 15 16  1  0
 16 14  2  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 15 23  1  0
 20 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 26 31  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3964042

   ---

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: 492.33

Molecular Weight (Monoisotopic): 491.0368

AlogP: 5.49

#Rotatable Bonds: 4

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.70

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.73

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: -0.51

References

1. Baiceanu E, Nguyen KA, Gonzalez-Lobato L, Nasr R, Baubichon-Cortay H, Loghin F, Le Borgne M, Chow L, Boumendjel A, Peuchmaur M, Falson P..  (2016)  2-Indolylmethylenebenzofuranones as first effective inhibitors of ABCC2.,  122  [PMID:27393949] [10.1016/j.ejmech.2016.06.039]

2. Jedlitschky, G G and 5 more authors.  1997-10-01  ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2.  [PMID:9355767]

Source

Source(1):

• Scientific Literature