7-Aziridin-1-yl-2-phenyl-quinoline-5,8-dione

ID: ALA105522

PubChem CID: 24853870

Max Phase: Preclinical

Molecular Formula: C17H12N2O2

Molecular Weight: 276.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(N2CC2)C(=O)c2nc(-c3ccccc3)ccc21

Standard InChI:  InChI=1S/C17H12N2O2/c20-15-10-14(19-8-9-19)17(21)16-12(15)6-7-13(18-16)11-4-2-1-3-5-11/h1-7,10H,8-9H2

Standard InChI Key:  VDYWTWQAJRAUGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   -0.9458    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583    0.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917    0.3333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -0.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    2.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000    1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  1  1  0
  5  1  2  0
  6  2  1  0
  7  8  1  0
  8  5  1  0
  9  4  1  0
 10  4  1  0
 11  6  2  0
 12  7  1  0
 13  3  2  0
 14  8  2  0
 15 12  2  0
 16 11  1  0
 17 16  1  0
 18 16  2  0
 19 18  1  0
 20 17  2  0
 21 19  2  0
  9 10  1  0
  7  2  2  0
 15 11  1  0
 21 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA105522

   7-(Aziridin-1-yl)-2-phenylquinoline-5,8-dione

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: 276.30

Molecular Weight (Monoisotopic): 276.0899

AlogP: 2.33

#Rotatable Bonds: 2

Polar Surface Area: 50.04

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.94

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: -0.15

References

1. Hargreaves R, David CL, Whitesell L, Skibo EB..  (2003)  Design of quinolinedione-based geldanamycin analogues.,  13  (18): [PMID:12941337] [10.1016/s0960-894x(03)00650-4]

2. Hargreaves RH, David CL, Whitesell LJ, Labarbera DV, Jamil A, Chapuis JC, Skibo EB..  (2008)  Discovery of quinolinediones exhibiting a heat shock response and angiogenesis inhibition.,  51  (8): [PMID:18363347] [10.1021/jm7014099]

Source

Source(1):

• Scientific Literature