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

ID: ALA4074087

PubChem CID: 137641225

Max Phase: Preclinical

Molecular Formula: C22H20N2O2

Molecular Weight: 344.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCc1c(CO)c2n(c1-c1ccccc1)CCc1c-2[nH]c2ccccc12

Standard InChI:  InChI=1S/C22H20N2O2/c25-12-17-18(13-26)22-20-16(15-8-4-5-9-19(15)23-20)10-11-24(22)21(17)14-6-2-1-3-7-14/h1-9,23,25-26H,10-13H2

Standard InChI Key:  ZZDBOAWCKDLQRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.4105   -9.9908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8848   -9.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3988   -8.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6255   -8.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9144   -8.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2074   -8.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2156   -9.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9308  -10.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6337   -9.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3126   -9.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0155   -9.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8368   -8.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0211   -8.4842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5352   -7.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7220   -7.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6980   -9.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3755   -7.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1174   -7.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6561   -6.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4569   -6.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7192   -7.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1764   -8.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2326  -10.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8989  -11.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7636   -9.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4196   -9.1931    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
 12 17  1  0
 23 24  1  0
 10 23  1  0
 25 26  1  0
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4074087

   ---

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: 344.41

Molecular Weight (Monoisotopic): 344.1525

AlogP: 3.84

#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: 2.94

CX LogD: 2.94

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: 0.17

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