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

ID: ALA2332688

PubChem CID: 44819149

Max Phase: Preclinical

Molecular Formula: C17H12N2O3

Molecular Weight: 292.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2c[nH]c3c2C(=O)c2cc[nH]c2C3=O)cc1

Standard InChI:  InChI=1S/C17H12N2O3/c1-22-10-4-2-9(3-5-10)12-8-19-15-13(12)16(20)11-6-7-18-14(11)17(15)21/h2-8,18-19H,1H3

Standard InChI Key:  WHRBKXYATFHGDI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   17.0826   -3.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0814   -4.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7966   -4.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5134   -4.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5106   -3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7948   -2.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3677   -2.8850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3675   -2.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2249   -4.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3125   -5.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1202   -5.5256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9784   -4.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5323   -4.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3358   -4.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2280   -3.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0380   -3.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5888   -3.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3430   -3.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2582   -2.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4516   -2.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6739   -2.8006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8892   -5.2511    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
  1  7  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 13  1  0
 12  9  1  0
  4  9  1  0
 12 13  2  0
 12 15  1  0
 13 14  1  0
 14 17  1  0
 16 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 16  1  0
 15 21  2  0
 14 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332688

   3-(4-Methoxyphenyl)-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: 292.29

Molecular Weight (Monoisotopic): 292.0848

AlogP: 2.79

#Rotatable Bonds: 2

Polar Surface Area: 74.95

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.60

CX Basic pKa: ┄

CX LogP: 2.41

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: 0.82

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