IDEBENONE

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Search structure


Synonyms	Hydroxydecyl ubiquinone Idebenone NSC-759228 Oristar hdu Raxone Sovrima
Status
Molecule Category	UNKNOWN
ATC	N06BX13
UNII	HB6PN45W4J
EPA CompTox	DTXSID0040678


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	JGPMMRGNQUBGND-UHFFFAOYSA-N
Smiles	COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O
InChI	InChI=1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H30O5
Molecular Weight	338.44
AlogP	3.46
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	12.0
Polar Surface Area	72.83
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	24.0

Bioactivity

Mechanism of Action	Action	Reference
Antioxidant and mitochondrial electron carrier	None	EMA PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	-	-	-	27
Enzyme Transferase	-	1900	-	-	-
Epigenetic regulator Eraser Histone deacetylase HDAC class III	-	15400	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of human FAAH at 1 uM	Homo sapiens	26.92 %
Cytoprotectant activity against L-buthionine-(S,R)-sulfoximine-induced cell death in Friedreich ataxia patient fibroblasts assessed as increase of cell viability	Homo sapiens	850.0 nM
DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	None	800.0 nM
Cytoprotective activity against BSO-induced human FRDA primary patient fibroblasts compound pretreated 12 hrs prior to BSO-induction measured after 48 hrs by calcein-AM-based cell viability assay	Homo sapiens	592.0 nM
Cytoprotection in diethyl maleate-treated human Friedreich's ataxia lymphocytes incubated for 17 hrs before diethyl maleate challenge by trypan blue dye exclusion method	Homo sapiens	730.0 nM
Inhibition of lipid peroxidation in diethyl maleate-treated human Friedreich's ataxia lymphocytes at 5 uM pre-incubated for 16 hrs before diethyl maleate challenge by FACS method relative to untreated control	Homo sapiens	77.0 %
Inhibition of lipid peroxidation in diethyl maleate-treated human Friedreich's ataxia lymphocytes at 2.5 uM pre-incubated for 16 hrs before diethyl maleate challenge by FACS method relative to untreated control	Homo sapiens	68.0 %
Inhibition of NADH oxidase in bovine heart submitochondrial particles at 10 uM after 5 mins by spectrophotometric analysis relative to untreated control	Bos taurus	13.4 %
Inhibition of NADH oxidase in bovine heart submitochondrial particles at 5 uM after 5 mins by spectrophotometric analysis relative to untreated control	Bos taurus	20.3 %
Inhibition of NADH oxidase in bovine heart submitochondrial particles at 1 uM after 5 mins by spectrophotometric analysis relative to untreated control	Bos taurus	58.3 %
Inhibition of NADH oxidase activity of bovine heart mitochondrial complexes 1, 2 and 3 at 10 uM after 5 mins by spectrophotometric analysis relative to control	Bos taurus	13.2 %
Inhibition of NADH oxidase activity of bovine heart mitochondrial complexes 1, 2 and 3 at 5 uM after 5 mins by spectrophotometric analysis relative to control	Bos taurus	19.3 %
Inhibition of NADH oxidase activity of bovine heart mitochondrial complexes 1, 2 and 3 at 1 uM after 5 mins by spectrophotometric analysis relative to control	Bos taurus	57.4 %
Cytoprotective activity against BSO-induced cell death in human Friedreich's ataxia lymphocytes preincubated for 12 hrs prior to BSO-treatment measured after 48 hrs by luminescence assay	Homo sapiens	551.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-2.88 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.63 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.09 %
Suppression of rotenone-induced ATP depletion in human HepG2 cells incubated for 2 hrs by Celltiter-Glo assay	Homo sapiens	940.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	31687
ChEMBL	CHEMBL252556
DrugCentral	1416
FDA SRS	HB6PN45W4J
PubChem	3686
SureChEMBL	SCHEMBL28320
ZINC	ZINC000001542890

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).