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

ID: ALA4079048

PubChem CID: 137650104

Max Phase: Preclinical

Molecular Formula: C18H20N2O2

Molecular Weight: 296.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CO)c(CO)c2n1CCc1c-2n(C)c2ccccc12

Standard InChI:  InChI=1S/C18H20N2O2/c1-11-14(9-21)15(10-22)18-17-13(7-8-20(11)18)12-5-3-4-6-16(12)19(17)2/h3-6,21-22H,7-10H2,1-2H3

Standard InChI Key:  JUUKXMRXHHHFCQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    9.3774   -8.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8564   -7.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3751   -7.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5942   -7.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8844   -7.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1760   -7.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1774   -8.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8872   -8.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5956   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2823   -8.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9907   -7.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8227   -7.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0039   -7.0710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5226   -6.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7082   -6.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6749   -7.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6292   -9.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3695   -6.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1997   -9.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8638   -9.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7427   -8.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4051   -7.8077    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
  1 17  1  0
 12 18  1  0
 19 20  1  0
 10 19  1  0
 21 22  1  0
 11 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079048

   ---

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: 296.37

Molecular Weight (Monoisotopic): 296.1525

AlogP: 2.50

#Rotatable Bonds: 2

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: 1.79

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 0.05

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