5-((2,5-Dioxopyrrolidin-1-yl)methyl)-N-hydroxy-[1,1'-biphenyl]-2-carboxamide

ID: ALA4776962

PubChem CID: 162643782

Max Phase: Preclinical

Molecular Formula: C18H16N2O4

Molecular Weight: 324.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(CN2C(=O)CCC2=O)cc1-c1ccccc1

Standard InChI:  InChI=1S/C18H16N2O4/c21-16-8-9-17(22)20(16)11-12-6-7-14(18(23)19-24)15(10-12)13-4-2-1-3-5-13/h1-7,10,24H,8-9,11H2,(H,19,23)

Standard InChI Key:  XJSCTVQZGQHBJQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   11.5887  -16.7231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2951  -16.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0041  -16.7189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8449  -16.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5094  -17.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7106  -17.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3010  -17.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6721  -15.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0046  -17.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7127  -17.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4201  -17.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4150  -16.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7064  -16.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1296  -17.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1331  -18.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8355  -17.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5450  -17.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1181  -16.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8287  -16.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5333  -16.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5284  -15.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8131  -15.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1115  -15.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1170  -18.0838    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  1  0
  4  8  2  0
  3  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  3  1  0
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 12 18  1  0
  5 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776962

   ---

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: 324.34

Molecular Weight (Monoisotopic): 324.1110

AlogP: 2.12

#Rotatable Bonds: 4

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: 8.94

CX Basic pKa: ┄

CX LogP: 1.45

CX LogD: 1.44

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -0.82

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