N-(1-Acetyl-1H-indol-3-yl)-N-(3-hydroxyphenyl)acetamide

ID: ALA3809511

PubChem CID: 127043083

Max Phase: Preclinical

Molecular Formula: C18H16N2O3

Molecular Weight: 308.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N(c1cccc(O)c1)c1cn(C(C)=O)c2ccccc12

Standard InChI:  InChI=1S/C18H16N2O3/c1-12(21)19-11-18(16-8-3-4-9-17(16)19)20(13(2)22)14-6-5-7-15(23)10-14/h3-11,23H,1-2H3

Standard InChI Key:  LIIDNOUGDCDVCV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3877   -3.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606   -2.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1812    2.6271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6500    2.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1200    4.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886    4.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5873    3.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1174    2.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6488    1.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1824    3.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5580    4.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0075    3.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645    5.8050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 13 20  1  0
 20 21  2  0
 20 22  1  0
 16 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3809511

   ---

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: 308.34

Molecular Weight (Monoisotopic): 308.1161

AlogP: 3.69

#Rotatable Bonds: 2

Polar Surface Area: 62.54

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.14

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.79

Np Likeness Score: -0.67

References

1. Unzue A, Zhao H, Lolli G, Dong J, Zhu J, Zechner M, Dolbois A, Caflisch A, Nevado C..  (2016)  The "Gatekeeper" Residue Influences the Mode of Binding of Acetyl Indoles to Bromodomains.,  59  (7): [PMID:26982797] [10.1021/acs.jmedchem.5b01757]

Source

Source(1):

• Scientific Literature