N-hydroxy-2,2-diphenylacetamide

ID: ALA396097

Chembl Id: CHEMBL396097

Cas Number: 4099-51-8

PubChem CID: 239512

Max Phase: Preclinical

Molecular Formula: C14H13NO2

Molecular Weight: 227.26

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(NO)C(c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C14H13NO2/c16-14(15-17)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13,17H,(H,15,16)

Standard InChI Key:  OFSBBVCLWMCGNY-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

HDAC8 Tclin Histone deacetylase 8 (4516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC7 Tclin Histone deacetylase 7 (1047 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC5 Tclin Histone deacetylase 5 (941 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC4 Tclin Histone deacetylase 4 (2328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC2 Tclin Histone deacetylase 2 (3971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC1 Tclin Histone deacetylase 1 (10854 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC1 Tclin Histone deacetylase (6747 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC3 Tclin Histone deacetylase 3 (3654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC9 Tclin Histone deacetylase 9 (708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC10 Tclin Histone deacetylase 10 (801 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC11 Tclin Histone deacetylase 11 (967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC3 Tclin Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) (735 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

rep Replicase polyprotein 1ab (11336 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 227.26Molecular Weight (Monoisotopic): 227.0946AlogP: 2.32#Rotatable Bonds: 3
Polar Surface Area: 49.33Molecular Species: NEUTRALHBA: 2HBD: 2
#RO5 Violations: 0HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 8.78CX Basic pKa: CX LogP: 2.48CX LogD: 2.46
Aromatic Rings: 2Heavy Atoms: 17QED Weighted: 0.62Np Likeness Score: -0.41

References

1. Krennhrubec K, Marshall BL, Hedglin M, Verdin E, Ulrich SM..  (2007)  Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors.,  17  (10): [PMID:17346959] [10.1016/j.bmcl.2007.02.064]
2. Tessier P, Smil DV, Wahhab A, Leit S, Rahil J, Li Z, Déziel R, Besterman JM..  (2009)  Diphenylmethylene hydroxamic acids as selective class IIa histone deacetylase inhibitors.,  19  (19): [PMID:19699639] [10.1016/j.bmcl.2009.08.010]
3. Bürli RW, Luckhurst CA, Aziz O, Matthews KL, Yates D, Lyons KA, Beconi M, McAllister G, Breccia P, Stott AJ, Penrose SD, Wall M, Lamers M, Leonard P, Müller I, Richardson CM, Jarvis R, Stones L, Hughes S, Wishart G, Haughan AF, O'Connell C, Mead T, McNeil H, Vann J, Mangette J, Maillard M, Beaumont V, Munoz-Sanjuan I, Dominguez C..  (2013)  Design, synthesis, and biological evaluation of potent and selective class IIa histone deacetylase (HDAC) inhibitors as a potential therapy for Huntington's disease.,  56  (24): [PMID:24261862] [10.1021/jm4011884]
4. Li Y, Woster PM..  (2015)  Discovery of a new class of histone deacetylase inhibitors with a novel zinc binding group.,  (4): [PMID:26005563] [10.1039/c4md00401a]
5. Luckhurst CA, Aziz O, Beaumont V, Bürli RW, Breccia P, Maillard MC, Haughan AF, Lamers M, Leonard P, Matthews KL, Raphy G, Stott AJ, Munoz-Sanjuan I, Thomas B, Wall M, Wishart G, Yates D, Dominguez C..  (2019)  Development and characterization of a CNS-penetrant benzhydryl hydroxamic acid class IIa histone deacetylase inhibitor.,  29  (1): [PMID:30463802] [10.1016/j.bmcl.2018.11.009]
6. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]
7. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]
8. Tilekar K, Hess JD, Upadhyay N, Bianco AL, Schweipert M, Laghezza A, Loiodice F, Meyer-Almes FJ, Aguilera RJ, Lavecchia A, C S R..  (2021)  Thiazolidinedione "Magic Bullets" Simultaneously Targeting PPARγ and HDACs: Design, Synthesis, and Investigations of their In Vitro and In Vivo Antitumor Effects.,  64  (10.0): [PMID:34006099] [10.1021/acs.jmedchem.1c00491]