2-Morpholinoethyl-5,12-dioxo-5,12-dihydroindolizino[2,3-g]phthalazine-11-carboxylate

ID: ALA4176746

PubChem CID: 145972451

Max Phase: Preclinical

Molecular Formula: C21H18N4O5

Molecular Weight: 406.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2cnncc2C(=O)c2c1c(C(=O)OCCN1CCOCC1)c1ccccn21

Standard InChI:  InChI=1S/C21H18N4O5/c26-19-13-11-22-23-12-14(13)20(27)18-17(19)16(15-3-1-2-4-25(15)18)21(28)30-10-7-24-5-8-29-9-6-24/h1-4,11-12H,5-10H2

Standard InChI Key:  CGNVQIMMQLXXOR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   17.2477  -31.7920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9530  -32.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9530  -30.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6582  -30.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6548  -31.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3568  -32.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3638  -30.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3661  -29.7498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3522  -33.0185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.3267  -31.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8452  -32.0466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1699  -32.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -32.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4586  -32.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1329  -31.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2511  -30.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0683  -30.0105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8366  -29.3131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4828  -30.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3000  -30.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7145  -31.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3084  -32.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7194  -32.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5370  -32.8170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9418  -32.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5290  -31.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  2  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5  8  1  0
  6  7  1  0
  7 12  1  0
 11  8  1  0
  8  9  2  0
  7 10  2  0
 11 12  2  0
 12 15  1  0
 14 13  2  0
 13 11  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4176746

   ---

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: 406.40

Molecular Weight (Monoisotopic): 406.1277

AlogP: 0.99

#Rotatable Bonds: 4

Polar Surface Area: 103.10

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.59

CX LogP: 0.08

CX LogD: 0.08

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -0.93

References

1. Yu Q, Yang H, Zhu TW, Yu LM, Chen JW, Gu LQ, Huang ZS, An LK..  (2018)  Synthesis, cytotoxicity and structure-activity relationship of indolizinoquinolinedione derivatives as DNA topoisomerase IB catalytic inhibitors.,  152  [PMID:29705710] [10.1016/j.ejmech.2018.04.040]

Source

Source(1):

• Scientific Literature