Acetic acid 6-aziridin-1-yl-7-methyl-5,8-dioxo-1,2,3,4,5,8-hexahydro-cyclopenta[b]indol-3-yl ester

ID: ALA118248

PubChem CID: 9796346

Max Phase: Preclinical

Molecular Formula: C16H16N2O4

Molecular Weight: 300.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC1CCc2c1[nH]c1c2C(=O)C(C)=C(N2CC2)C1=O

Standard InChI:  InChI=1S/C16H16N2O4/c1-7-14(18-5-6-18)16(21)13-11(15(7)20)9-3-4-10(12(9)17-13)22-8(2)19/h10,17H,3-6H2,1-2H3

Standard InChI Key:  UOTSMBYMYVNAFJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    4.6792   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -3.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -3.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6000   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -2.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -3.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -1.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2125   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -1.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -2.8417    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  3  2  0
  9  2  1  0
 10  4  1  0
 11  8  1  0
 12 10  1  0
 13 10  1  0
 14  3  1  0
 15 11  1  0
 16  5  2  0
 17  7  2  0
 18 15  1  0
 19 14  1  0
 20 18  2  0
 21  6  1  0
 22 18  1  0
  9  8  1  0
  4  5  1  0
 11 19  1  0
 13 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA118248

   [6-(Aziridin-1-yl)-7-methyl-5,8-dioxo-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl] acetate

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: 300.31

Molecular Weight (Monoisotopic): 300.1110

AlogP: 1.53

#Rotatable Bonds: 2

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: 9.67

CX Basic pKa: ┄

CX LogP: 0.52

CX LogD: 0.51

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.66

Np Likeness Score: 0.96

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