(E)-2-(4-Nitrostyryl)-4-(1-piperidinylethyl)aminoquinazoline

ID: ALA4776273

PubChem CID: 162642983

Max Phase: Preclinical

Molecular Formula: C23H25N5O2

Molecular Weight: 403.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc(/C=C/c2nc(NCCN3CCCCC3)c3ccccc3n2)cc1

Standard InChI:  InChI=1S/C23H25N5O2/c29-28(30)19-11-8-18(9-12-19)10-13-22-25-21-7-3-2-6-20(21)23(26-22)24-14-17-27-15-4-1-5-16-27/h2-3,6-13H,1,4-5,14-17H2,(H,24,25,26)/b13-10+

Standard InChI Key:  WZKVALSTKMFZAO-JLHYYAGUSA-N

Molfile:  

 
     RDKit          2D

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   13.5029   -4.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5017   -5.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2098   -5.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2080   -3.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9166   -4.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9174   -5.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6259   -5.4281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3342   -5.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3294   -4.1951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6203   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0435   -5.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7496   -5.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4589   -5.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4574   -6.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1658   -6.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8729   -6.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8671   -5.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1581   -5.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6160   -2.9746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3215   -2.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0314   -2.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7369   -2.5547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4454   -2.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1489   -2.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1488   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4390   -1.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7294   -1.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5830   -6.6323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2886   -6.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5873   -7.4495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
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  9 10  2  0
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  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 10 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 28 29  2  0
 28 30  1  0
 16 28  1  0
M  CHG  2  28   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4776273

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 403.49

Molecular Weight (Monoisotopic): 403.2008

AlogP: 4.61

#Rotatable Bonds: 7

Polar Surface Area: 84.19

Molecular Species: BASE

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.77

CX LogP: 5.48

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -1.35

References

1. Wei XW,Yuan JM,Huang WY,Chen NY,Li XJ,Pan CX,Mo DL,Su GF.  (2020)  2-Styryl-4-aminoquinazoline derivatives as potent DNA-cleavage, p53-activation and in vivo effective anticancer agents.,  186  [PMID:31761381] [10.1016/j.ejmech.2019.111851]

Source

Source(1):

• Scientific Literature