1-[(4-methoxyphenyl)methyl]indole-5-carbohydroxamic acid

ID: ALA5203725

PubChem CID: 168293537

Max Phase: Preclinical

Molecular Formula: C17H16N2O3

Molecular Weight: 296.33

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2ccc3cc(C(=O)NO)ccc32)cc1

Standard InChI:  InChI=1S/C17H16N2O3/c1-22-15-5-2-12(3-6-15)11-19-9-8-13-10-14(17(20)18-21)4-7-16(13)19/h2-10,21H,11H2,1H3,(H,18,20)

Standard InChI Key:  BQOSUTIJKDOCIO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.0386    1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532    1.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    1.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550    0.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386    0.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7491    1.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492    0.4919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2361    1.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7492   -0.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4664   -0.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1824    1.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1824    2.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8997    1.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170    1.9909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667   -1.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1822   -1.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8997   -1.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9013   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1868   -0.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170   -1.9908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170   -2.8191    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
  1  7  1  0
  6  8  1  0
  8  9  1  0
  9  7  2  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 16 11  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 11 20  1  0
 18 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5203725

   ---

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: 296.33

Molecular Weight (Monoisotopic): 296.1161

AlogP: 2.82

#Rotatable Bonds: 4

Polar Surface Area: 63.49

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.02

CX Basic pKa: ┄

CX LogP: 2.71

CX LogD: 2.70

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -1.11

References

1. Sun P, Wang J, Khan KS, Yang W, Ng BW, Ilment N, Zessin M, Bülbül EF, Robaa D, Erdmann F, Schmidt M, Romier C, Schutkowski M, Cheng AS, Sippl W..  (2022)  Development of Alkylated Hydrazides as Highly Potent and Selective Class I Histone Deacetylase Inhibitors with T cell Modulatory Properties.,  65  (24.0): [PMID:36449385] [10.1021/acs.jmedchem.2c01132]

Source

Source(1):

• Scientific Literature