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

ID: ALA3914655

PubChem CID: 134143225

Max Phase: Preclinical

Molecular Formula: C19H14BrNO4

Molecular Weight: 400.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCn1cc(/C=C2\Oc3cc(O)cc(O)c3C2=O)c2cc(Br)ccc21

Standard InChI:  InChI=1S/C19H14BrNO4/c1-2-21-9-10(13-6-11(20)3-4-14(13)21)5-17-19(24)18-15(23)7-12(22)8-16(18)25-17/h3-9,22-23H,2H2,1H3/b17-5-

Standard InChI Key:  VBCKGYSXAORVOF-ZWSORDCHSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    1.5195  -20.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5184  -21.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332  -22.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314  -20.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470  -20.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518  -21.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438  -21.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284  -21.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358  -20.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8049  -20.5062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323  -22.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0033  -22.7815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0534  -21.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5407  -20.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9595  -19.3846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2906  -19.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6247  -19.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3650  -20.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9118  -21.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7182  -21.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9751  -20.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267  -19.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9626  -18.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2681  -21.7157    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.2497  -18.1442    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
M  END

Alternative Forms

1. Parent:

   

   ALA3914655

   ---

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: 400.23

Molecular Weight (Monoisotopic): 399.0106

AlogP: 4.45

#Rotatable Bonds: 2

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: 4.69

CX LogD: 4.52

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: -0.26

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