N-((4'-(2-Hexylhydrazinecarbonyl)-[1,1'-biphenyl]-4-yl)methyl)acetamide

ID: ALA5174998

PubChem CID: 168273030

Max Phase: Preclinical

Molecular Formula: C22H29N3O2

Molecular Weight: 367.49

Names and Identifiers

Canonical SMILES:  CCCCCCNNC(=O)c1ccc(-c2ccc(CNC(C)=O)cc2)cc1

Standard InChI:  InChI=1S/C22H29N3O2/c1-3-4-5-6-15-24-25-22(27)21-13-11-20(12-14-21)19-9-7-18(8-10-19)16-23-17(2)26/h7-14,24H,3-6,15-16H2,1-2H3,(H,23,26)(H,25,27)

Standard InChI Key:  TYHZHMRYNRDNRX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.8611    1.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750    1.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2906    1.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1455    1.4498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328    1.0384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7172    1.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160    2.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0033    1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123    1.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4279    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0033    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750   -1.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    0.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2888   -1.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0045   -1.0364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7178   -1.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4335   -1.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7167   -2.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042    1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7200    1.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4335    1.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  5  4  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  9  8  2  0
 10  9  1  0
 11 10  2  0
 11 12  1  0
  8 13  1  0
 13 12  2  0
 14 11  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 14 19  1  0
 17 20  1  0
 20 21  1  0
 22 21  1  0
 22 23  1  0
 22 24  2  0
  3 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5174998

   ---

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: 367.49

Molecular Weight (Monoisotopic): 367.2260

AlogP: 3.80

#Rotatable Bonds: 10

Polar Surface Area: 70.23

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.89

CX LogP: 3.56

CX LogD: 3.56

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: -0.76

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