2,3-Dioxo-2,3-dihydro-indole-1-carboxylic acid benzyl ester

ID: ALA119515

PubChem CID: 10468909

Max Phase: Preclinical

Molecular Formula: C16H11NO4

Molecular Weight: 281.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C(=O)N(C(=O)OCc2ccccc2)c2ccccc21

Standard InChI:  InChI=1S/C16H11NO4/c18-14-12-8-4-5-9-13(12)17(15(14)19)16(20)21-10-11-6-2-1-3-7-11/h1-9H,10H2

Standard InChI Key:  YDHPGKMAVWLLPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.6042   -0.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    0.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042    1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    0.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -1.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    1.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -1.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1417   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  2  2  0
  8  6  1  0
  9  4  2  0
 10  6  2  0
 11  8  1  0
 12  3  2  0
 13  5  2  0
 14 11  1  0
 15 14  2  0
 16 14  1  0
 17 12  1  0
 18 17  2  0
 19 16  2  0
 20 15  1  0
 21 19  1  0
  5  4  1  0
 18 13  1  0
 21 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA119515

   2,3-Dioxo-2,3-dihydro-indole-1-carboxylic acid benzyl ester

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: 281.27

Molecular Weight (Monoisotopic): 281.0688

AlogP: 2.55

#Rotatable Bonds: 2

Polar Surface Area: 63.68

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: -0.27

References

1. Chiyanzu I, Hansell E, Gut J, Rosenthal PJ, McKerrow JH, Chibale K..  (2003)  Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.,  13  (20): [PMID:14505663] [10.1016/s0960-894x(03)00756-x]

2. Iyer RA, Hanna PE.  (1995)  N-(carbobenzyloxy)isatin: A slow binding -keto lactam inhibitor of -chymotrypsin,  5  (1): [10.1016/0960-894X(94)00464-Q]

3. Ettari R, Tamborini L, Angelo IC, Micale N, Pinto A, De Micheli C, Conti P..  (2013)  Inhibition of rhodesain as a novel therapeutic modality for human African trypanosomiasis.,  56  (14): [PMID:23611656] [10.1021/jm301424d]

Source

Source(1):

• Scientific Literature