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

ID: ALA3945493

PubChem CID: 134146560

Max Phase: Preclinical

Molecular Formula: C22H21NO4

Molecular Weight: 363.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c(/C=C2\Oc3cc(O)cc(O)c3C2=O)c(C)c2ccccc21

Standard InChI:  InChI=1S/C22H21NO4/c1-3-4-9-23-16-8-6-5-7-15(16)13(2)17(23)12-20-22(26)21-18(25)10-14(24)11-19(21)27-20/h5-8,10-12,24-25H,3-4,9H2,1-2H3/b20-12-

Standard InChI Key:  AJFDIQBBWVOEGI-NDENLUEZSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   16.9532   -3.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9521   -4.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6601   -5.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6583   -3.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3670   -3.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3718   -4.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1562   -4.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6362   -4.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1484   -3.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2454   -3.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6592   -5.9129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4132   -5.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4534   -4.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9360   -3.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7545   -3.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6873   -2.8271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3510   -2.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0068   -2.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7511   -2.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8409   -1.6965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1803   -1.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4386   -1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9694   -2.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9487   -1.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2308   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5337   -1.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2330   -4.2707    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 15  2  0
 15 18  1  0
 17 16  1  0
 16 14  1  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
 16 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 15 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3945493

   ---

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: 363.41

Molecular Weight (Monoisotopic): 363.1471

AlogP: 4.78

#Rotatable Bonds: 4

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: 5.32

CX LogD: 5.15

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: 0.14

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