(E)-6-((3-(dimethylamino)propyl)amino)-7-fluoro-3-(4-hydroxy-3,5-dimethoxybenzylidene)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one

ID: ALA4096008

PubChem CID: 137652701

Max Phase: Preclinical

Molecular Formula: C25H29FN4O4

Molecular Weight: 468.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CCn3c2nc2cc(NCCCN(C)C)c(F)cc2c3=O)cc(OC)c1O

Standard InChI:  InChI=1S/C25H29FN4O4/c1-29(2)8-5-7-27-20-14-19-17(13-18(20)26)25(32)30-9-6-16(24(30)28-19)10-15-11-21(33-3)23(31)22(12-15)34-4/h10-14,27,31H,5-9H2,1-4H3/b16-10+

Standard InChI Key:  QQEHSTCDODGLOS-MHWRWJLKSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   10.5753   -6.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8266   -7.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6228   -7.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8748   -7.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6743   -8.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2201   -7.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9703   -6.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1743   -6.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9695   -5.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9683   -5.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6805   -6.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6787   -4.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3832   -5.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862   -6.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0882   -6.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906   -4.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0906   -3.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562   -6.4155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5405   -6.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8366   -6.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7994   -5.1827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8020   -6.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0558   -5.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5778   -4.9302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2544   -4.7736    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264   -6.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4212   -6.4271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110   -6.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262   -7.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0189   -7.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9243   -8.9325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3755   -9.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5200   -6.1668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3185   -6.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
 10 11  1  0
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 13 16  1  0
 14 15  1  0
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 21 16  1  0
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 10 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  1  0
 22  1  1  0
  1 23  1  0
 23 24  1  0
 24 21  1  0
  9 25  1  0
 20 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
  5 31  1  0
 31 32  1  0
  7 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096008

   ---

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: 468.53

Molecular Weight (Monoisotopic): 468.2173

AlogP: 3.57

#Rotatable Bonds: 8

Polar Surface Area: 88.85

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.06

CX Basic pKa: 9.66

CX LogP: 1.66

CX LogD: 0.38

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: -0.65

References

1. Wang YQ, Huang ZL, Chen SB, Wang CX, Shan C, Yin QK, Ou TM, Li D, Gu LQ, Tan JH, Huang ZS..  (2017)  Design, Synthesis, and Evaluation of New Selective NM23-H2 Binders as c-MYC Transcription Inhibitors via Disruption of the NM23-H2/G-Quadruplex Interaction.,  60  (16): [PMID:28714689] [10.1021/acs.jmedchem.7b00421]

Source

Source(1):

• Scientific Literature