(Z)-2-(N-Butyl-5-bromoindol-3-ylmethylene)-4,6-dihydroxybenzofuran-3(2H)-one

ID: ALA3948408

PubChem CID: 134147852

Max Phase: Preclinical

Molecular Formula: C21H18BrNO4

Molecular Weight: 428.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1cc(/C=C2\Oc3cc(O)cc(O)c3C2=O)c2cc(Br)ccc21

Standard InChI:  InChI=1S/C21H18BrNO4/c1-2-3-6-23-11-12(15-8-13(22)4-5-16(15)23)7-19-21(26)20-17(25)9-14(24)10-18(20)27-19/h4-5,7-11,24-25H,2-3,6H2,1H3/b19-7-

Standard InChI Key:  WWJJWRURBBYWDQ-GXHLCREISA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   12.5241  -21.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5230  -22.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2378  -22.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2359  -20.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9514  -21.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9563  -22.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7482  -22.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2328  -21.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7403  -20.9442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8095  -20.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2368  -23.2745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0077  -23.0720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0578  -21.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5451  -20.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9638  -19.6753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2949  -20.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6290  -20.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3693  -20.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9160  -21.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7225  -21.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9793  -20.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4309  -19.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9669  -18.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2723  -22.0062    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   16.2540  -18.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5379  -18.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8250  -18.4295    0.0000 C   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
 23 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3948408

   ---

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: 428.28

Molecular Weight (Monoisotopic): 427.0419

AlogP: 5.23

#Rotatable Bonds: 4

Polar Surface Area: 71.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.70

CX Basic pKa: ┄

CX LogP: 5.66

CX LogD: 5.48

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.56

Np Likeness Score: -0.35

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