(2Z)-2-(indol-1-ylmethylene)-6-methoxy-benzofuran-3-one

ID: ALA5278614

Max Phase: Preclinical

Molecular Formula: C18H13NO3

Molecular Weight: 291.31

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)O/C(=C\n1ccc3ccccc31)C2=O

Standard InChI:  InChI=1S/C18H13NO3/c1-21-13-6-7-14-16(10-13)22-17(18(14)20)11-19-9-8-12-4-2-3-5-15(12)19/h2-11H,1H3/b17-11-

Standard InChI Key:  MOODQNGPTAEDTA-BOPFTXTBSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -2.4118    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972    0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9853    0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9853   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954   -1.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118   -0.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006   -0.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    0.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2843   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0129   -1.7562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5221    0.4229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264    0.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8411    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6809    1.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154    1.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3231    0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732    1.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8411    1.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7510    0.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9936    0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  1  0
  9  7  1  0
  7 10  2  0
  9 11  2  0
 11 12  1  0
  1 13  1  0
 13 14  1  0
 15 12  1  0
 15 16  2  0
 16 17  1  0
 18 17  2  0
 12 18  1  0
 17 19  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278614

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 291.31

Molecular Weight (Monoisotopic): 291.0895

AlogP: 3.72

#Rotatable Bonds: 2

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: -0.37

References

1. Lazinski LM, Royal G, Robin M, Maresca M, Haudecoeur R..  (2022)  Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives.,  65  (19.0): [PMID:36126323] [10.1021/acs.jmedchem.2c01150]

Source

Source(1):

• Scientific Literature