6-Aziridin-1-yl-3-methoxy-7-methyl-1,2,3,4-tetrahydro-cyclopenta[b]indole-5,8-dione

ID: ALA118112

PubChem CID: 10423363

Max Phase: Preclinical

Molecular Formula: C15H16N2O3

Molecular Weight: 272.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1CCc2c1[nH]c1c2C(=O)C(C)=C(N2CC2)C1=O

Standard InChI:  InChI=1S/C15H16N2O3/c1-7-13(17-5-6-17)15(19)12-10(14(7)18)8-3-4-9(20-2)11(8)16-12/h9,16H,3-6H2,1-2H3

Standard InChI Key:  RTWIJJQPNQKKBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
    5.1917   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -3.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -3.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -3.1917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  6  2  0
  5  2  1  0
  6  7  1  0
  7  1  1  0
  8  2  1  0
  9  3  2  0
 10  4  1  0
 11 10  1  0
 12 10  1  0
 13  3  1  0
 14  5  2  0
 15  9  1  0
 16  7  2  0
 17 13  1  0
 18  6  1  0
 19 15  1  0
 20 19  1  0
  8  9  1  0
  5  4  1  0
 15 17  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA118112

   6-(Aziridin-1-yl)-3-methoxy-7-methyl-1,2,3,4-tetrahydrocyclopenta[b]indole-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: 272.30

Molecular Weight (Monoisotopic): 272.1161

AlogP: 1.62

#Rotatable Bonds: 2

Polar Surface Area: 62.17

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.99

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: 0.72

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: 0.81

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