5-(2,4-dihydroxy-5-isopropyl-phenyl)-4-(4-piperidin-1-ylmethyl-phenyl)-isoxazole-3-carboxylic acid ethylamide

ID: ALA252370

Chembl Id: CHEMBL252370

PubChem CID: 135517488

Max Phase: Preclinical

Molecular Formula: C27H33N3O4

Molecular Weight: 463.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)c1noc(-c2cc(C(C)C)c(O)cc2O)c1-c1ccc(CN2CCCCC2)cc1

Standard InChI:  InChI=1S/C27H33N3O4/c1-4-28-27(33)25-24(19-10-8-18(9-11-19)16-30-12-6-5-7-13-30)26(34-29-25)21-14-20(17(2)3)22(31)15-23(21)32/h8-11,14-15,17,31-32H,4-7,12-13,16H2,1-3H3,(H,28,33)

Standard InChI Key:  FQKHRMZPORXQSR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA252370

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 463.58

Molecular Weight (Monoisotopic): 463.2471

AlogP: 5.28

#Rotatable Bonds: 7

Polar Surface Area: 98.83

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.42

CX Basic pKa: 10.05

CX LogP: 3.79

CX LogD: 2.99

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -0.50

References

1. Brough PA, Aherne W, Barril X, Borgognoni J, Boxall K, Cansfield JE, Cheung KM, Collins I, Davies NG, Drysdale MJ, Dymock B, Eccles SA, Finch H, Fink A, Hayes A, Howes R, Hubbard RE, James K, Jordan AM, Lockie A, Martins V, Massey A, Matthews TP, McDonald E, Northfield CJ, Pearl LH, Prodromou C, Ray S, Raynaud FI, Roughley SD, Sharp SY, Surgenor A, Walmsley DL, Webb P, Wood M, Workman P, Wright L..  (2008)  4,5-diarylisoxazole Hsp90 chaperone inhibitors: potential therapeutic agents for the treatment of cancer.,  51  (2): [PMID:18020435] [10.1021/jm701018h]

2. Sakkiah S, Thangapandian S, John S, Kwon YJ, Lee KW..  (2010)  3D QSAR pharmacophore based virtual screening and molecular docking for identification of potential HSP90 inhibitors.,  45  (6): [PMID:20206418] [10.1016/j.ejmech.2010.01.016]

3. Meng T, Zhang D, Xie Z, Yu T, Wu S, Wyder L, Regenass U, Hilpert K, Huang M, Geng M, Shen J..  (2014)  Discovery and optimization of 4,5-diarylisoxazoles as potent dual inhibitors of pyruvate dehydrogenase kinase and heat shock protein 90.,  57  (23): [PMID:25383915] [10.1021/jm5010144]

4. Yin W, Wu T, Liu L, Jiang H, Zhang Y, Cui H, Sun Y, Qin Q, Sun Y, Gao Z, Zhao L, Su X, Zhao D, Cheng M..  (2022)  Species-Selective Targeting of Fungal Hsp90: Design, Synthesis, and Evaluation of Novel 4,5-Diarylisoxazole Derivatives for the Combination Treatment of Azole-Resistant Candidiasis.,  65  (7.0): [PMID:35298171] [10.1021/acs.jmedchem.1c01991]

Source

Source(1):

• Scientific Literature