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

ID: ALA3928271

PubChem CID: 134140743

Max Phase: Preclinical

Molecular Formula: C24H22BrNO4

Molecular Weight: 468.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1/C(=C/c2cn(CC3CCCCC3)c3ccc(Br)cc23)Oc2cc(O)cc(O)c21

Standard InChI:  InChI=1S/C24H22BrNO4/c25-16-6-7-19-18(9-16)15(13-26(19)12-14-4-2-1-3-5-14)8-22-24(29)23-20(28)10-17(27)11-21(23)30-22/h6-11,13-14,27-28H,1-5,12H2/b22-8-

Standard InChI Key:  OLPWWAZBULMGSC-UYOCIXKTSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    2.1778  -27.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767  -28.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8915  -28.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8897  -27.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052  -27.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6101  -28.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4020  -28.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866  -27.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3940  -27.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4632  -27.1266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906  -29.6043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6615  -29.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7116  -27.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1988  -27.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6176  -26.0049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487  -26.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2828  -26.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0232  -27.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5699  -27.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3762  -27.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6332  -26.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0848  -26.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6207  -25.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9262  -28.3359    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.9078  -24.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9121  -23.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2032  -23.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4848  -23.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796  -24.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929  -25.1765    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
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3928271

   ---

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: 468.35

Molecular Weight (Monoisotopic): 467.0732

AlogP: 6.01

#Rotatable Bonds: 3

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: 6.45

CX LogD: 6.27

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -0.20

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