CHEBI:43645 - indirubin-3'-monoxime

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ChEBI Name indirubin-3'-monoxime
ChEBI ID CHEBI:43645
Definition A member of the class of biindoles that is indirubin in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB1325944, eMolecules:1934826, ZINC000100001998
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Formula C16H11N3O2
Net Charge 0
Average Mass 277.278
Monoisotopic Mass 277.08513
InChI InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+
InChIKey HBDSHCUSXQATPO-BGBJRWHRSA-N
SMILES N1/C(/C(/C2=C1C=CC=C2)=N/O)=C/3\C(NC4=C3C=CC=C4)=O
Roles Classification
Biological Role(s): EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of non-specific serine/threonine protein kinase (EC 2.7.11.1), a kinase enzyme involved in phosphorylation of hydroxy group of serine or threonine.
osteogenesis regulator
Any compound that induces or regulates osteogenesis.
anti-obesity agent
Any substance which is used to reduce or control weight.
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of cyclin-dependent kinase (EC 2.7.11.22).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing indirubin-3'-monoxime (CHEBI:43645) has role anti-obesity agent (CHEBI:74518)
indirubin-3'-monoxime (CHEBI:43645) has role EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor (CHEBI:50925)
indirubin-3'-monoxime (CHEBI:43645) has role EC 2.7.11.22 (cyclin-dependent kinase) inhibitor (CHEBI:82665)
indirubin-3'-monoxime (CHEBI:43645) has role neuroprotective agent (CHEBI:63726)
indirubin-3'-monoxime (CHEBI:43645) has role osteogenesis regulator (CHEBI:63054)
indirubin-3'-monoxime (CHEBI:43645) is a alkaloid (CHEBI:22315)
indirubin-3'-monoxime (CHEBI:43645) is a bisindole (CHEBI:51877)
indirubin-3'-monoxime (CHEBI:43645) is a ketoxime (CHEBI:24983)
indirubin-3'-monoxime (CHEBI:43645) is a oxindoles (CHEBI:38459)
indirubin-3'-monoxime (CHEBI:43645) is a ring assembly (CHEBI:36820)
IUPAC Name
(3Z)-3-[(3E)-3-(hydroxyimino)-1,3-dihydro-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one
Synonyms Sources
1H,1'H-[2,3']biindolylidene3,2'-dione-3-oxime ChEBI
indirubin-3'-oxime ChEBI
Manual Xrefs Databases
DB02052 DrugBank
IXM PDBeChem
View more database links
Registry Number Type Source
7594308 Reaxys Registry Number Reaxys
Citations
Udumula MP, Medapi B, Dhar I, Bhat A, Desai K, Sriram D, Dhar A (2016)
The Small Molecule Indirubin-3'-Oxime Inhibits Protein Kinase R: Antiapoptotic and Antioxidant Effect in Rat Cardiac Myocytes.
Pharmacology 97, 25-30 [PubMed:26571010]
[show Abstract]
Hu S, Cui W, Zhang Z, Mak S, Xu D, Li G, Hu Y, Wang Y, Lee M, Tsim KW, Han Y (2015)
Indirubin-3-Oxime Effectively Prevents 6OHDA-Induced Neurotoxicity in PC12 Cells via Activating MEF2D Through the Inhibition of GSK3β.
Journal of molecular neuroscience : MN 57, 561-570 [PubMed:26346600]
[show Abstract]
Sharma S, Taliyan R (2014)
Neuroprotective role of Indirubin-3'-monoxime, a GSKβ inhibitor in high fat diet induced cognitive impairment in mice.
Biochemical and biophysical research communications 452, 1009-1015 [PubMed:25234596]
[show Abstract]
Zahoor M, Cha PH, Choi KY (2014)
Indirubin-3'-oxime, an activator of Wnt/β-catenin signaling, enhances osteogenic commitment of ST2 cells and restores bone loss in high-fat diet-induced obese male mice.
Bone 65, 60-68 [PubMed:24815917]
[show Abstract]
Choi OM, Cho YH, Choi S, Lee SH, Seo SH, Kim HY, Han G, Min DS, Park T, Choi KY (2014)
The small molecule indirubin-3'-oxime activates Wnt/β-catenin signaling and inhibits adipocyte differentiation and obesity.
International journal of obesity (2005) 38, 1044-1052 [PubMed:24232498]
[show Abstract]
Zahoor M, Cha PH, Min do S, Choi KY (2014)
Indirubin-3'-oxime reverses bone loss in ovariectomized and hindlimb-unloaded mice via activation of the Wnt/β-catenin signaling.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 29, 1196-1205 [PubMed:24243753]
[show Abstract]
Lee JJ, Han JH, Jung SH, Lee SG, Kim IS, Cuong NM, Huong TT, Khanh PN, Kim YH, Yun YP, Ma JY, Myung CS (2014)
Antiplatelet action of indirubin-3'-monoxime through suppression of glycoprotein VI-mediated signal transduction: a possible role for ERK signaling in platelets.
Vascular pharmacology 63, 182-192 [PubMed:25451564]
[show Abstract]
Liao XM, Leung KN (2013)
Indirubin-3'-oxime induces mitochondrial dysfunction and triggers growth inhibition and cell cycle arrest in human neuroblastoma cells.
Oncology reports 29, 371-379 [PubMed:23117445]
[show Abstract]
Jung HJ, Nam KN, Son MS, Kang H, Hong JW, Kim JW, Lee EH (2011)
Indirubin-3'-oxime inhibits inflammatory activation of rat brain microglia.
Neuroscience letters 487, 139-143 [PubMed:20946938]
[show Abstract]
Mapelli M, Massimiliano L, Crovace C, Seeliger MA, Tsai LH, Meijer L, Musacchio A (2005)
Mechanism of CDK5/p25 binding by CDK inhibitors.
Journal of medicinal chemistry 48, 671-679 [PubMed:15689152]
[show Abstract]
Bertrand JA, Thieffine S, Vulpetti A, Cristiani C, Valsasina B, Knapp S, Kalisz HM, Flocco M (2003)
Structural characterization of the GSK-3beta active site using selective and non-selective ATP-mimetic inhibitors.
Journal of molecular biology 333, 393-407 [PubMed:14529625]
[show Abstract]
Last Modified
30 November 2015