THYMOQUINONE

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Search structure


Synonyms	NSC-2228 P-cymene-2,5-dione P-mentha-3,6-diene-2,5-dione Thymoquinon Thymoquinone
Status
Molecule Category	UNKNOWN
UNII	O60IE26NUF
EPA CompTox	DTXSID9060079


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

Structure


InChI Key	KEQHJBNSCLWCAE-UHFFFAOYSA-N
Smiles	CC1=CC(=O)C(C(C)C)=CC1=O
InChI	InChI=1S/C10H12O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6H,1-3H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C10H12O2
Molecular Weight	164.2
AlogP	1.67
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	1.0
Polar Surface Area	34.14
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	12.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	Electrophorus electricus	7.9 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method	Equus caballus	-0.33 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	126.43 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	98.24 %
Antileishmanial activity against Leishmania tropica MHOM/IR/2002/Mash2 assessed as cell viability after 72 hrs by MTT assay	Leishmania tropica	1.16 ug.mL-1
Antileishmanial activity against Leishmania infantum MCAN/IR/07/Moheb-gh assessed as cell viability after 72 hrs by MTT assay	Leishmania infantum	1.47 ug.mL-1
Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay	Homo sapiens	300.0 nM
Cytotoxicity against human CEM/ADR5000 cells over-expressing P-gp assessed as reduction in cell viability after 72 hrs by resazurin dye based assay	Homo sapiens	300.0 nM
Cytotoxicity against human CCRF-CEM cells assessed as reduction in cell viability after 72 hrs by resazurin dye based assay	Homo sapiens	300.0 nM
Cytotoxicity against human CEM/ADR5000 cells overexpressing P-gp assessed as reduction in cell viability after 72 hrs by resazurin dye based assay	Homo sapiens	300.0 nM

Cross References

Resources	Reference
ChEBI	113532
ChEMBL	CHEMBL1672002
FDA SRS	O60IE26NUF
Human Metabolome Database	HMDB0034732
PDB	IMW
PubChem	10281
SureChEMBL	SCHEMBL542535
ZINC	ZINC000000164367

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).