N'-Butyl-[1,1'-biphenyl]-4-carbohydrazide

ID: ALA4761444

PubChem CID: 118418386

Max Phase: Preclinical

Molecular Formula: C17H20N2O

Molecular Weight: 268.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCNNC(=O)c1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C17H20N2O/c1-2-3-13-18-19-17(20)16-11-9-15(10-12-16)14-7-5-4-6-8-14/h4-12,18H,2-3,13H2,1H3,(H,19,20)

Standard InChI Key:  WRMLHFIPUNMIQC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   12.2099  -10.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9220  -10.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9197   -9.5605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6366  -10.7958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3487  -10.3779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3464   -9.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0586   -9.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0521   -8.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7643   -7.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4931  -10.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7814  -10.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7867  -11.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5098  -12.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2186  -11.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0788  -12.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3611  -11.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6509  -12.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6574  -12.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3799  -13.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0870  -12.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  2  3  2  0
  2  4  1  0
  1  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5  6  1  0
  1 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  1  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761444

   N'-butyl-4-phenylbenzohydrazide

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: 268.36

Molecular Weight (Monoisotopic): 268.1576

AlogP: 3.39

#Rotatable Bonds: 6

Polar Surface Area: 41.13

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.89

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: -0.86

References

1. McClure JJ,Zhang C,Inks ES,Peterson YK,Li J,Chou CJ.  (2016)  Development of Allosteric Hydrazide-Containing Class I Histone Deacetylase Inhibitors for Use in Acute Myeloid Leukemia.,  59  (21): [PMID:27754681] [10.1021/acs.jmedchem.6b01385]

2. He X, Hui Z, Xu L, Bai R, Gao Y, Wang Z, Xie T, Ye XY..  (2022)  Medicinal chemistry updates of novel HDACs inhibitors (2020 to present).,  227  [PMID:34775332] [10.1016/j.ejmech.2021.113946]

3. 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