5-Aziridin-1-yl-2-hydroxymethyl-3,6-dimethyl-1H-indole-4,7-dione

ID: ALA342473

PubChem CID: 9813608

Max Phase: Preclinical

Molecular Formula: C13H14N2O3

Molecular Weight: 246.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(N2CC2)C(=O)c2c([nH]c(CO)c2C)C1=O

Standard InChI:  InChI=1S/C13H14N2O3/c1-6-8(5-16)14-10-9(6)13(18)11(15-3-4-15)7(2)12(10)17/h14,16H,3-5H2,1-2H3

Standard InChI Key:  ARVYALYBJUWXGA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
    6.2750   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2375   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2375   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -5.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -6.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -5.8125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -5.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2000   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -5.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -5.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -5.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500   -7.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000   -5.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  5  1  0
  4  3  2  0
  5  1  1  0
  6  2  1  0
  7  2  1  0
  8  3  1  0
  9  1  1  0
 10  9  2  0
 11  8  1  0
 12  8  1  0
 13  5  2  0
 14  7  2  0
 15  4  1  0
 16 10  1  0
 17  9  1  0
 18 16  1  0
 10  6  1  0
  4  7  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA342473

   5-Aziridinyl-2-(hydroxymethyl)-3,6-dimethylindole-4,7-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: 246.27

Molecular Weight (Monoisotopic): 246.1004

AlogP: 0.78

#Rotatable Bonds: 2

Polar Surface Area: 73.17

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.24

CX Basic pKa: ┄

CX LogP: 0.04

CX LogD: 0.04

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.76

Np Likeness Score: 0.57

References

1. Xing C, Wu P, Skibo EB, Dorr RT..  (2000)  Design of cancer-specific antitumor agents based on aziridinylcyclopent[b]indoloquinones.,  43  (3): [PMID:10669573] [10.1021/jm990466w]

Source

Source(1):

• Scientific Literature