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

ID: ALA332884

PubChem CID: 10106557

Max Phase: Preclinical

Molecular Formula: C14H14N2O3

Molecular Weight: 258.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(N2CC2)C(=O)c2[nH]c3c(c2C1=O)CCC3O

Standard InChI:  InChI=1S/C14H14N2O3/c1-6-12(16-4-5-16)14(19)11-9(13(6)18)7-2-3-8(17)10(7)15-11/h8,15,17H,2-5H2,1H3

Standard InChI Key:  JRPBLAMSAWRTGS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 22  0  0  0  0  0  0  0  0999 V2000
    4.9250   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -3.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -3.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -3.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000   -1.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -2.7417    0.0000 O   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
  8  9  1  0
  5  4  1  0
 15 17  1  0
 12 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA332884

   6-(Aziridin-1-yl)-3-hydroxy-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: 258.28

Molecular Weight (Monoisotopic): 258.1004

AlogP: 0.96

#Rotatable Bonds: 1

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: 11.00

CX Basic pKa: ┄

CX LogP: 0.07

CX LogD: 0.07

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.74

Np Likeness Score: 0.80

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