(3-(4-Fluorophenyl)-6,11-dihydro-5H-indolizino [8,7-b]indole-1,2-diyl)dimethanol

ID: ALA4060557

PubChem CID: 137635411

Max Phase: Preclinical

Molecular Formula: C22H19FN2O2

Molecular Weight: 362.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCc1c(CO)c2n(c1-c1ccc(F)cc1)CCc1c-2[nH]c2ccccc12

Standard InChI:  InChI=1S/C22H19FN2O2/c23-14-7-5-13(6-8-14)21-17(11-26)18(12-27)22-20-16(9-10-25(21)22)15-3-1-2-4-19(15)24-20/h1-8,24,26-27H,9-12H2

Standard InChI Key:  GFOXTTCHDJYDOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    9.4984   -9.5408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9771   -8.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4996   -8.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7214   -8.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0181   -8.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3073   -8.4641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3040   -9.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0114   -9.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222   -9.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3962   -9.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1069   -8.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9395   -8.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1253   -8.0487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6478   -7.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8330   -7.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7920   -8.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4857   -7.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2383   -6.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7845   -6.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5863   -6.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8337   -7.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2875   -7.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1325   -5.7151    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.3088  -10.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9701  -10.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8529   -9.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5140   -8.7952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  1  9  1  0
  4  9  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10 16  2  0
 13 16  1  0
  2 16  1  0
  3 15  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 17 22  2  0
 20 23  1  0
 12 17  1  0
 24 25  1  0
 10 24  1  0
 26 27  1  0
 11 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4060557

   ---

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: 362.40

Molecular Weight (Monoisotopic): 362.1431

AlogP: 3.98

#Rotatable Bonds: 3

Polar Surface Area: 61.18

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.14

References

1. Chang SM, Christian W, Wu MH, Chen TL, Lin YW, Suen CS, Pidugu HB, Detroja D, Shah A, Hwang MJ, Su TL, Lee TC..  (2017)  Novel indolizino[8,7-b]indole hybrids as anti-small cell lung cancer agents: Regioselective modulation of topoisomerase II inhibitory and DNA crosslinking activities.,  127  [PMID:28064078] [10.1016/j.ejmech.2016.12.046]

Source

Source(1):

• Scientific Literature