2-(3-Chlorophenyl)-2-(3-(1,3-dioxoisoindolin-2-yl)-propoxy)-N-hydroxyacetamide

ID: ALA4760192

PubChem CID: 162658728

Max Phase: Preclinical

Molecular Formula: C19H17ClN2O5

Molecular Weight: 388.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)C(OCCCN1C(=O)c2ccccc2C1=O)c1cccc(Cl)c1

Standard InChI:  InChI=1S/C19H17ClN2O5/c20-13-6-3-5-12(11-13)16(17(23)21-26)27-10-4-9-22-18(24)14-7-1-2-8-15(14)19(22)25/h1-3,5-8,11,16,26H,4,9-10H2,(H,21,23)

Standard InChI Key:  MVQRLAQQXSXLMD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.8389  -13.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5454  -12.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2543  -13.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608  -12.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6698  -12.9960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3762  -12.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0852  -12.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3738  -11.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0856  -11.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0835  -10.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740  -10.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6652  -10.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6708  -11.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0876  -13.8090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7916  -12.5811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5006  -12.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952  -12.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7597  -13.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9609  -13.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513  -13.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366  -13.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306  -13.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452  -14.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585  -14.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3673  -14.3652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9223  -11.8730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9553  -10.1437    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  7 14  2  0
  7 15  1  0
 15 16  1  0
  1 17  1  0
 17 20  1  0
 19 18  1  0
 18  1  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 18 25  2  0
 17 26  2  0
 12 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760192

   ---

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: 388.81

Molecular Weight (Monoisotopic): 388.0826

AlogP: 2.59

#Rotatable Bonds: 7

Polar Surface Area: 95.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.58

CX Basic pKa: ┄

CX LogP: 2.14

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: -0.94

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