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

ID: ALA4094619

PubChem CID: 137652601

Max Phase: Preclinical

Molecular Formula: C23H22N2O2

Molecular Weight: 358.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c2c(c3ccccc31)CCn1c(-c3ccccc3)c(CO)c(CO)c1-2

Standard InChI:  InChI=1S/C23H22N2O2/c1-24-20-10-6-5-9-16(20)17-11-12-25-21(15-7-3-2-4-8-15)18(13-26)19(14-27)23(25)22(17)24/h2-10,26-27H,11-14H2,1H3

Standard InChI Key:  XAXBQCGLCBZREN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 31  0  0  0  0  0  0  0  0999 V2000
    8.2053   -7.6135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6796   -6.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1937   -6.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4203   -6.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7093   -6.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0022   -6.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0104   -7.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7256   -7.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4285   -7.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1075   -7.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8104   -6.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6317   -6.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8159   -6.1069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3300   -5.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5168   -5.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4928   -6.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1704   -5.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9123   -4.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4509   -4.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2518   -4.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5140   -5.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9712   -5.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0274   -8.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6938   -8.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5585   -7.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2145   -6.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4659   -8.3880    0.0000 C   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
 12 17  1  0
 23 24  1  0
 10 23  1  0
 25 26  1  0
 11 25  1  0
  1 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4094619

   ---

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: 358.44

Molecular Weight (Monoisotopic): 358.1681

AlogP: 3.85

#Rotatable Bonds: 3

Polar Surface Area: 50.32

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 0.06

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