3-(4-hydroxyphenyl)pyrrolo[3,2-f]indole-4,8(1H,7H)-dione

ID: ALA2332689

PubChem CID: 44819151

Max Phase: Preclinical

Molecular Formula: C16H10N2O3

Molecular Weight: 278.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2[nH]ccc2C(=O)c2c(-c3ccc(O)cc3)c[nH]c21

Standard InChI:  InChI=1S/C16H10N2O3/c19-9-3-1-8(2-4-9)11-7-18-14-12(11)15(20)10-5-6-17-13(10)16(14)21/h1-7,17-19H

Standard InChI Key:  MLUVGEIMYYIBHA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  0  0  0  0  0  0  0  0999 V2000
   24.4515   -3.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4504   -4.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1658   -4.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8830   -4.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8802   -3.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1640   -2.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5993   -4.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6870   -5.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4950   -5.4942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3531   -4.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9043   -4.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7043   -4.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6021   -3.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4086   -3.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9609   -3.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7081   -3.4815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6175   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8144   -2.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7362   -2.8530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0481   -2.7716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2568   -5.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 11  1  0
 10  7  1  0
  4  7  1  0
 10 11  2  0
 10 13  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  1 19  1  0
 13 20  2  0
 12 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332689

   3-(4-Hydroxyphenyl)-1,7-dihydropyrrolo[3,2-f]indole-4,8-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: 278.27

Molecular Weight (Monoisotopic): 278.0691

AlogP: 2.49

#Rotatable Bonds: 1

Polar Surface Area: 85.95

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.26

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.50

Np Likeness Score: 1.17

References

1. Dolušić E, Larrieu P, Meinguet C, Colette D, Rives A, Blanc S, Ferain T, Pilotte L, Stroobant V, Wouters J, Van den Eynde B, Masereel B, Delfourne E, Frédérick R..  (2013)  Indoleamine 2,3-dioxygenase inhibitory activity of derivatives of marine alkaloid tsitsikammamine A.,  23  (1): [PMID:23218716] [10.1016/j.bmcl.2012.11.036]

Source

Source(1):

• Scientific Literature