Acetic acid 5-aziridin-1-yl-3,6-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-2-ylmethyl ester

ID: ALA119517

PubChem CID: 9943807

Max Phase: Preclinical

Molecular Formula: C15H16N2O4

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCc1[nH]c2c(c1C)C(=O)C(N1CC1)=C(C)C2=O

Standard InChI:  InChI=1S/C15H16N2O4/c1-7-10(6-21-9(3)18)16-12-11(7)15(20)13(17-4-5-17)8(2)14(12)19/h16H,4-6H2,1-3H3

Standard InChI Key:  GTTCFXOKHIDTRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    4.7167   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7250   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -3.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -1.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -3.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -2.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542   -2.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -3.0125    0.0000 C   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 17  1  0
 16 10  1  0
 17 16  1  0
 18 15  2  0
 19  4  1  0
 20  9  1  0
 21 15  1  0
  6 10  1  0
  4  7  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA119517

   2-(Acetoxymethyl)-5-aziridinyl-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: 288.30

Molecular Weight (Monoisotopic): 288.1110

AlogP: 1.35

#Rotatable Bonds: 3

Polar Surface Area: 79.24

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.22

CX Basic pKa: ┄

CX LogP: 0.49

CX LogD: 0.49

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: 0.53

References

1. Skibo EB, Xing C, Dorr RT..  (2001)  Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: structure-activity relationships for cytotoxicity and antitumor activity.,  44  (22): [PMID:11606119] [10.1021/jm010085u]

2. 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