(E)-4-(3-(3-Bromo-4-hydroxyphenyl)-2-(hydroxyimino)-propanamido)-N-hydroxybutanamide

ID: ALA2047685

Max Phase: Preclinical

Molecular Formula: C13H16BrN3O5

Molecular Weight: 374.19

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: O=C(CCCNC(=O)/C(Cc1ccc(O)c(Br)c1)=N/O)NO

Standard InChI: InChI=1S/C13H16BrN3O5/c14-9-6-8(3-4-11(9)18)7-10(16-21)13(20)15-5-1-2-12(19)17-22/h3-4,6,18,21-22H,1-2,5,7H2,(H,15,20)(H,17,19)/b16-10+

Standard InChI Key: BGUDCWHWRPWMRI-MHWRWJLKSA-N

Molfile:

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    4.5103   -6.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7940   -7.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -6.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3663   -7.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5111   -5.9672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -7.2024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9383   -6.7937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -7.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2275   -6.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -7.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9421   -8.0226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -6.7887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283   -5.9630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4872   -5.5481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043   -6.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9165   -7.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6319   -6.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6311   -5.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9148   -5.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035   -5.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3466   -5.5494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3441   -7.1982    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
  8 12  1  0
 13 14  1  0
  9 13  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 18 21  1  0
 17 22  1  0
 10 15  1  0
  4 12  1  0
M  END

Associated Targets(Human)

HDAC1 Tclin Histone deacetylase 1 (10854 Activities)

Discover Target: HDAC1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC6 Tclin Histone deacetylase 6 (20808 Activities)

Discover Target: HDAC6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC3 Tclin Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) (735 Activities)

Discover Target: HDAC3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HDAC2 Tclin Histone deacetylase 2 (3971 Activities)

Discover Target: HDAC2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HL-60 (67320 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 374.19	Molecular Weight (Monoisotopic): 373.0273	AlogP: 0.93	#Rotatable Bonds: 7
Polar Surface Area: 131.25	Molecular Species: NEUTRAL	HBA: 6	HBD: 5
#RO5 Violations: ┄	HBA (Lipinski): 8	HBD (Lipinski): 5	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 7.94	CX Basic pKa: ┄	CX LogP: 0.99	CX LogD: 0.87
Aromatic Rings: 1	Heavy Atoms: 22	QED Weighted: 0.16	Np Likeness Score: 0.34

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98. Li, Yongtao Y and 13 more authors. 2018-04-12 Discovery of N1-(4-((7-Cyclopentyl-6-(dimethylcarbamoyl)-7 H-pyrrolo[2,3- d]pyrimidin-2-yl)amino)phenyl)- N8-hydroxyoctanediamide as a Novel Inhibitor Targeting Cyclin-dependent Kinase 4/9 (CDK4/9) and Histone Deacetlyase1 (HDAC1) against Malignant Cancer. [PMID:29518312]
99. Rabal, Obdulia O and 15 more authors. 2018-04-25 Design, synthesis, biological evaluation and in vivo testing of dual phosphodiesterase 5 (PDE5) and histone deacetylase 6 (HDAC6)-selective inhibitors for the treatment of Alzheimer's disease. [PMID:29549837]
100. Ojha, Ritu R and 10 more authors. 2018-04-25 1-Aroylindoline-hydroxamic acids as anticancer agents, inhibitors of HSP90 and HDAC. [PMID:29567459]
101. Sellmer, Andreas A and 13 more authors. 2018-04-26 Marbostat-100 Defines a New Class of Potent and Selective Antiinflammatory and Antirheumatic Histone Deacetylase 6 Inhibitors. [PMID:29589441]
102. Zang, Jie J and 7 more authors. 2018-06-28 Discovery of Novel Pazopanib-Based HDAC and VEGFR Dual Inhibitors Targeting Cancer Epigenetics and Angiogenesis Simultaneously. [PMID:29787262]
103. Huang, Yahui Y and 5 more authors. 2018-07-26 Discovery of Janus Kinase 2 (JAK2) and Histone Deacetylase (HDAC) Dual Inhibitors as a Novel Strategy for the Combinational Treatment of Leukemia and Invasive Fungal Infections. [PMID:29940115]
104. Lee, Hsueh-Yun HY and 11 more authors. 2018-08-23 5-Aroylindoles Act as Selective Histone Deacetylase 6 Inhibitors Ameliorating Alzheimer's Disease Phenotypes. [PMID:30028616]
105. Porter, Nicholas J and 6 more authors. 2018-09-13 Histone Deacetylase 6-Selective Inhibitors and the Influence of Capping Groups on Hydroxamate-Zinc Denticity. [PMID:30118224]
106. Chu-Farseeva, Yu-Yi YY and 6 more authors. 2018-10-05 Design and synthesis of potent dual inhibitors of JAK2 and HDAC based on fusing the pharmacophores of XL019 and vorinostat. [PMID:30243158]
107. Diedrich, Daniela D and 14 more authors. 2018-10-05 One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites. [PMID:30245402]
108. Bhatia, Sanil S and 10 more authors. 2018-11-21 Discovery of the First-in-Class Dual Histone Deacetylase-Proteasome Inhibitor. [PMID:30365892]
109. Bouchut, Anne A and 16 more authors. 2019-01-01 Identification of novel quinazoline derivatives as potent antiplasmodial agents. [PMID:30366254]
110. Lai, Mei-Jung MJ and 11 more authors. 2019-01-15 1-Arylsulfonyl indoline-benzamides as a new antitubulin agents, with inhibition of histone deacetylase. [PMID:30476825]
111. Zhou, Ruolan R and 10 more authors. 2019-02-01 Design, synthesis, and bioactivity evaluation of novel Bcl-2/HDAC dual-target inhibitors for the treatment of multiple myeloma. [PMID:30594434]
112. Song, Yoojin Y, Lim, Jiah J and Seo, Young Ho YH. 2019-02-15 A novel class of anthraquinone-based HDAC6 inhibitors. [PMID:30597327]
113. Chen, Yong Y and 10 more authors. 2019-02-14 Discovery of Novel Dual Histone Deacetylase and Mammalian Target of Rapamycin Target Inhibitors as a Promising Strategy for Cancer Therapy. [PMID:30629434]
114. Vögerl, Katharina and 15 more authors. 2019-02-14 Synthesis and Biological Investigation of Phenothiazine-Based Benzhydroxamic Acids as Selective Histone Deacetylase 6 Inhibitors. [PMID:30645113]
115. Ling, Yong Y and 11 more authors. 2019-04-15 β-Carboline and N-hydroxycinnamamide hybrids as anticancer agents for drug-resistant hepatocellular carcinoma. [PMID:30851694]
116. Ling, Yong Y and 12 more authors. 2019-06-28 Hydroxamic Acid Derivatives of β-Carboline/Hydroxycinnamic Acid Hybrids Inducing Apoptosis and Autophagy through the PI3K/Akt/mTOR Pathways. [PMID:31120744]
117. Yang, Zhuang Z and 10 more authors. 2019-09-15 Discovery of 1,2,4-oxadiazole-Containing hydroxamic acid derivatives as histone deacetylase inhibitors potential application in cancer therapy. [PMID:31177073]
118. Cao, Fangyuan F and 5 more authors. 2019-09-01 Inhibitory selectivity among class I HDACs has a major impact on inflammatory gene expression in macrophages. [PMID:31181405]
119. Bouchet, Samuel S and 8 more authors. 2019-06-13 Extending Cross Metathesis To Identify Selective HDAC Inhibitors: Synthesis, Biological Activities, and Modeling. [PMID:31223439]
120. Nam, Gibeom G and 7 more authors. 2019-08-01 Structure-activity relationship study of thiazolyl-hydroxamate derivatives as selective histone deacetylase 6 inhibitors. [PMID:31235266]
121. Liu, Ruiqi R and 8 more authors. 2019-07-09 Design, synthesis, and biological evaluation of a new class of histone acetyltransferase p300 inhibitors. [PMID:31306905]
122. Reßing, Nina N and 9 more authors. 2019-07-01 Design, synthesis and biological evaluation of β-peptoid-capped HDAC inhibitors with anti-neuroblastoma and anti-glioblastoma activity. [PMID:31391882]
123. Liang, Tao T, Hou, Xuben X, Zhou, Yi Y, Yang, Xinying X and Fang, Hao H. 2019-08-08 Design, Synthesis, and Biological Evaluation of 2,4-Imidazolinedione Derivatives as HDAC6 Isoform-Selective Inhibitors. [PMID:31413795]
124. Shen, Sida S and 12 more authors. 2019-08-15 Discovery of a New Isoxazole-3-hydroxamate Based Histone Deacetylase 6 Inhibitor SS-208 with Anti-tumor Activity in Syngeneic Melanoma Mouse Models. [PMID:31414801]
125. Brindisi, Margherita M and 5 more authors. 2019-08-27 Old but Gold: Tracking the New Guise of Histone Deacetylase 6 (HDAC6) Enzyme as a Biomarker and Therapeutic Target in Rare Diseases. [PMID:31415174]
126. Wan, Yichao; Li, Yuanhua; Yan, Chunxing; Yan, Mi and Tang, Zilong. 2019-12-01 Indole: A privileged scaffold for the design of anti-cancer agents. [PMID:31536895]
127. Soumyanarayanan, Uttara and 8 more authors. 2019-12-15 Discovery of a potent histone deacetylase (HDAC) 3/6 selective dual inhibitor. [PMID:31627059]
128. Krieger, Viktoria and 10 more authors. 2019-12-26 Synthesis of Peptoid-Based Class I-Selective Histone Deacetylase Inhibitors with Chemosensitizing Properties. [PMID:31762274]
129. Wu, Ying and 6 more authors. 2020-01-09 Nicotinamide Phosphoribosyltransferase (NAMPT) Is a New Target of Antitumor Agent Chidamide. [PMID:31938461]
130. Ojha, Ritu and 14 more authors. 2020-03-15 Isoindoline scaffold-based dual inhibitors of HDAC6 and HSP90 suppressing the growth of lung cancer in vitro and in vivo. [PMID:32058238]
131. Wu, Bocheng and 5 more authors. 2020-03-15 Pyrimethamine conjugated histone deacetylase inhibitors: Design, synthesis and evidence for triple negative breast cancer selective cytotoxicity. [PMID:32061484]
132. Osko, Jeremy D and Christianson, David W. 2020-04-15 Structural determinants of affinity and selectivity in the binding of inhibitors to histone deacetylase 6. [PMID:32067866]
133. Tseng, Hui-Ju and 13 more authors. 2020-04-15 Synthesis and biological evaluation of acridine-based histone deacetylase inhibitors as multitarget agents against Alzheimer's disease. [PMID:32151835]
134. Pan, Zhaoping and 9 more authors. 2020-04-09 Discovery of Thieno[2,3-d]pyrimidine-Based Hydroxamic Acid Derivatives as Bromodomain-Containing Protein 4/Histone Deacetylase Dual Inhibitors Induce Autophagic Cell Death in Colorectal Carcinoma Cells. [PMID:32153186]
135. Nepali, Kunal and 7 more authors. 2020-06-15 Purine/purine isoster based scaffolds as new derivatives of benzamide class of HDAC inhibitors. [PMID:32325365]
136. Han, Guiyan and 5 more authors. 2020-05-28 Discovery of Novel Fungal Lanosterol 14α-Demethylase (CYP51)/Histone Deacetylase Dual Inhibitors to Treat Azole-Resistant Candidiasis. [PMID:32347094]
137. Tng, Jiahui and 6 more authors. 2020-06-11 Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class I HDAC Enzymes and Cancer Cell Proliferation. [PMID:32383881]
138. Romanelli, Annalisa and 14 more authors. 2020-05-14 Design of First-in-Class Dual EZH2/HDAC Inhibitor: Biochemical Activity and Biological Evaluation in Cancer Cells. [PMID:32435414]
139. Ghazy, Ehab and 12 more authors. 2020-08-15 Design, synthesis, and biological evaluation of dual targeting inhibitors of histone deacetylase 6/8 and bromodomain BRPF1. [PMID:32497960]
140. Gawel, Justyna M and 14 more authors. 2020-09-01 PTG-0861: A novel HDAC6-selective inhibitor as a therapeutic strategy in acute myeloid leukaemia. [PMID:32615502]
141. Huang, Ying and 6 more authors. 2020-09-01 The design of a novel near-infrared fluorescent HDAC inhibitor and image of tumor cells. [PMID:32773090]
142. Yao, Dahong and 6 more authors. 2020-11-01 Design, synthesis and biological evaluation of novel HDAC inhibitors with improved pharmacokinetic profile in breast cancer. [PMID:32791401]
143. Reßing, Nina and 11 more authors. 2020-09-24 Multicomponent Synthesis, Binding Mode, and Structure-Activity Relationship of Selective Histone Deacetylase 6 (HDAC6) Inhibitors with Bifurcated Capping Groups. [PMID:32803970]
144. Noonepalle, Satish and 12 more authors. 2020-09-24 Rational Design of Suprastat: A Novel Selective Histone Deacetylase 6 Inhibitor with the Ability to Potentiate Immunotherapy in Melanoma Models. [PMID:32815366]
145. Wei, Mingming and 14 more authors. 2020-11-15 Design and synthesis of novel Flavone-based histone deacetylase inhibitors antagonizing activation of STAT3 in breast cancer. [PMID:32823005]
146. Cao, Fangyuan and 5 more authors. 2020-12-15 Induced protein degradation of histone deacetylases 3 (HDAC3) by proteolysis targeting chimera (PROTAC). [PMID:32971411]
147. Gu, Xiaoke and 9 more authors. 2020-12-15 Discovery of thiosemicarbazone-containing compounds with potent anti-proliferation activity against drug-resistant K562/A02 cells. [PMID:33132117]
148. Relitti, Nicola and 17 more authors. 2021-02-15 Novel quinolone-based potent and selective HDAC6 inhibitors: Synthesis, molecular modeling studies and biological investigation. [PMID:33199154]
149. Mehndiratta, Samir and Liou, Jing-Ping. 2020-09-01 Histone lysine specific demethylase 1 inhibitors. [PMID:33479691]
150. Bao, Yu and 8 more authors. 2021-01-14 Studying Histone Deacetylase Inhibition and Apoptosis Induction of Psammaplin A Monomers with Modified Thiol Group. [PMID:33488962]
151. Zhao, Lei and 9 more authors. 2021-03-05 Design, synthesis and evaluation of novel ErbB/HDAC multitargeted inhibitors with selectivity in EGFRT790M mutant cell lines. [PMID:33493830]
152. Singh, Arshdeep and 8 more authors. 2021-02-06 CAP rigidification of MS-275 and chidamide leads to enhanced antiproliferative effects mediated through HDAC1, 2 and tubulin polymerization inhibition. [PMID:33588178]
153. Rabal, Obdulia and 16 more authors. 2021-03-04 Design and Synthesis of Novel Epigenetic Inhibitors Targeting Histone Deacetylases, DNA Methyltransferase 1, and Lysine Methyltransferase G9a with In Vivo Efficacy in Multiple Myeloma. [PMID:33661013]

(E)-4-(3-(3-Bromo-4-hydroxyphenyl)-2-(hydroxyimino)-propanamido)-N-hydroxybutanamide

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Associated Targets(non-human)

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References

Source