4-((1,3-Dioxoisoindolin-2-yl)methyl)-N-hydroxybenzamide

ID: ALA4762512

PubChem CID: 24758504

Max Phase: Preclinical

Molecular Formula: C16H12N2O4

Molecular Weight: 296.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(CN2C(=O)c3ccccc3C2=O)cc1

Standard InChI:  InChI=1S/C16H12N2O4/c19-14(17-22)11-7-5-10(6-8-11)9-18-15(20)12-3-1-2-4-13(12)16(18)21/h1-8,22H,9H2,(H,17,19)

Standard InChI Key:  YRRBSCMVOZIHKD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   12.1458  -11.9933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8523  -11.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5612  -11.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4021  -11.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0666  -12.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2678  -12.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8582  -12.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0435  -12.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6375  -12.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0521  -13.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8654  -13.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6742  -13.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2292  -10.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5618  -12.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2698  -13.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9773  -12.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9722  -11.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2636  -11.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6868  -13.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6903  -14.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3927  -12.7933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1022  -13.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  4  7  1  0
  6  5  1  0
  5  1  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  5 12  2  0
  4 13  2  0
  3 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762512

   4-[(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-methyl]-N-hydroxybenzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 296.28

Molecular Weight (Monoisotopic): 296.0797

AlogP: 1.60

#Rotatable Bonds: 3

Polar Surface Area: 86.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.05

CX Basic pKa: ┄

CX LogP: 1.49

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.51

Np Likeness Score: -0.97

References

1. Mak JYW,Wu KC,Gupta PK,Barbero S,McLaughlin MG,Lucke AJ,Tng J,Lim J,Loh Z,Sweet MJ,Reid RC,Liu L,Fairlie DP.  (2021)  HDAC7 Inhibition by Phenacetyl and Phenylbenzoyl Hydroxamates.,  64  (4.0): [PMID:33570940] [10.1021/acs.jmedchem.0c01967]

Source

Source(1):

• Scientific Literature