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

ID: ALA3974624

PubChem CID: 134154345

Max Phase: Preclinical

Molecular Formula: C25H25NO5

Molecular Weight: 419.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(/C=C1\Oc3cc(O)cc(O)c3C1=O)cn2CC1CCCCC1

Standard InChI:  InChI=1S/C25H25NO5/c1-30-18-7-8-20-19(12-18)16(14-26(20)13-15-5-3-2-4-6-15)9-23-25(29)24-21(28)10-17(27)11-22(24)31-23/h7-12,14-15,27-28H,2-6,13H2,1H3/b23-9-

Standard InChI Key:  RSUMRVJNHPFLEH-AQHIEDMUSA-N

Molfile:  

     RDKit          2D

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    1.9902   -5.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -6.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7038   -7.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020   -5.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174   -5.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4223   -6.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2141   -6.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6986   -6.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -5.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2756   -5.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029   -7.8359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736   -7.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5236   -6.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0108   -5.5051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296   -4.2368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7608   -4.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0948   -4.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8351   -5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3818   -6.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1881   -5.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4449   -5.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8966   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4327   -3.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7380   -6.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4802   -7.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199   -2.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7241   -2.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153   -1.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2918   -2.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050   -3.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  4  2  0
  4  1  1  0
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  6  7  1  0
  7  8  1  0
  8  9  1  0
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  1 10  1  0
  3 11  1  0
  7 12  2  0
  8 13  2  0
 13 14  1  0
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 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
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 31  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3974624

   ---

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: 419.48

Molecular Weight (Monoisotopic): 419.1733

AlogP: 5.26

#Rotatable Bonds: 4

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.70

CX Basic pKa: ┄

CX LogP: 5.52

CX LogD: 5.35

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.56

Np Likeness Score: -0.11

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