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

ID: ALA3921707

PubChem CID: 134139366

Max Phase: Preclinical

Molecular Formula: C18H12BrNO4

Molecular Weight: 386.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(/C=C2\Oc3cc(O)cc(O)c3C2=O)c2cc(Br)ccc21

Standard InChI:  InChI=1S/C18H12BrNO4/c1-20-8-9(12-5-10(19)2-3-13(12)20)4-16-18(23)17-14(22)6-11(21)7-15(17)24-16/h2-8,21-22H,1H3/b16-4-

Standard InChI Key:  PDOGVBARESRHII-XRVIQIRUSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   13.5994  -13.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5981  -13.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3130  -14.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3112  -12.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0266  -13.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0315  -13.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8234  -14.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3080  -13.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8155  -12.7523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8846  -12.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3120  -15.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0829  -14.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1331  -13.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6203  -12.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0390  -11.4833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3702  -11.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7042  -11.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4446  -12.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9913  -13.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7978  -13.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0546  -12.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5062  -11.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0422  -10.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3476  -13.8143    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
M  END

Alternative Forms

1. Parent:

   

   ALA3921707

   ---

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: 386.20

Molecular Weight (Monoisotopic): 384.9950

AlogP: 3.97

#Rotatable Bonds: 1

Polar Surface Area: 71.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.70

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 0.02

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