DIOSMIN

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Search structure


Synonyms	Barosmin Buchu resin Daflon Diosmetin 7-rutinoside Diosmin Diosven Dioven Diovenor Flebaven Flebavena Flebosmil Flebosten Hemerven Hesperidin Insuven Litosmil NSC-758417 Tovene Varinon Ven-detrex Venosmine
Status
Molecule Category	UNKNOWN
ATC	C05CA03
UNII	7QM776WJ5N
EPA CompTox	DTXSID4045892


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

Structure


InChI Key	GZSOSUNBTXMUFQ-YFAPSIMESA-N
Smiles	COc1ccc(-c2cc(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3o2)cc1O
InChI	InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C28H32O15
Molecular Weight	608.55
AlogP	-1.09
Hydrogen Bond Acceptor	15.0
Hydrogen Bond Donor	8.0
Number of Rotational Bond	7.0
Polar Surface Area	238.2
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	43.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of cow milk xanthine oxidase at 50 ug/mL	Bos taurus	0.0 %
Inhibition of electric eel AChE at 2 mg/ml by Ellman's method	Electrophorus electricus	9.59 %
Inhibition of horse BChE at 2 mg/ml by Ellman's method	Equus caballus	7.92 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	67.13 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	93.34 %
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	1.06 %
Inhibition of human recombinant full length PTP1B expressed in Escherichia coli cells at 1 uM using pNPP as substrate preincubated with enzyme for 5 mins followed by incubation with substrate for 10 mins by spectrophotometry analysis relative to control	Homo sapiens	36.26 %
Inhibition of human recombinant full length PTP1B expressed in Escherichia coli cells at 5 uM using pNPP as substrate preincubated with enzyme for 5 mins followed by incubation with substrate for 10 mins by spectrophotometry analysis relative to control	Homo sapiens	32.82 %
Inhibition of human recombinant full length PTP1B expressed in Escherichia coli cells at 10 uM using pNPP as substrate preincubated with enzyme for 5 mins followed by incubation with substrate for 10 mins by spectrophotometry analysis relative to control	Homo sapiens	30.53 %
Antihyperlipidemic activity in STZ-induced type-2 diabetes Kunming mouse model assessed as decrease in serum total cholesterol level at 100 mg/kg, po for 4 weeks relative to diabetic control	Mus musculus	8.3 %
Antihyperlipidemic activity in STZ-induced type-2 diabetes Kunming mouse model assessed as decrease in serum triglyceride level at 50 mg/kg, po for 4 weeks relative to diabetic control	Mus musculus	33.8 %
Antihyperlipidemic activity in STZ-induced type-2 diabetes Kunming mouse model assessed as decrease in serum triglyceride level at 100 mg/kg, po for 4 weeks relative to diabetic control	Mus musculus	27.3 %
Antidiabetic activity in STZ-induced type-2 diabetes Kunming mouse model assessed as decrease in blood glucose AUC at 50 mg/kg, po for 14 days followed by overnight fasting and later orally treated with maltose for 60 mins and measured after 120 mins by OMTT	Mus musculus	11.2 %
Antidiabetic activity in STZ-induced type-2 diabetes Kunming mouse model assessed as decrease in blood glucose AUC at 100 mg/kg, po for 14 days followed by overnight fasting and later orally treated with maltose for 60 mins and measured after 120 mins by OMTT	Mus musculus	13.5 %
Inhibition of F1F0-ATP synthase in Escherichia coli after 60 mins relative to control	Escherichia coli	40.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-5.263 %
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	0.19 %		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	0.19 %
Cytotoxicity against mouse C2C12 cells assessed as reduction in cell viability by MTT assay	Mus musculus	19.97 ug.mL-1

Related Entries

Cross References

Resources	Reference
ChEBI	4631
ChEMBL	CHEMBL231884
DrugBank	DB08995
DrugCentral	3157
FDA SRS	7QM776WJ5N
KEGG	C10039
PubChem	5281613
SureChEMBL	SCHEMBL120870
ZINC	ZINC000004098512

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).