BICYCLOL

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Search structure


Synonyms	Bicyclol
Status
Molecule Category	UNKNOWN
UNII	9734122TH2
EPA CompTox	DTXSID30152026


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

Structure


InChI Key	KXMTXZACPVCDMH-UHFFFAOYSA-N
Smiles	COC(=O)c1cc(OC)c2c(c1-c1c(CO)cc(OC)c3c1OCO3)OCO2
InChI	InChI=1S/C19H18O9/c1-22-11-4-9(6-20)13(17-15(11)25-7-27-17)14-10(19(21)24-3)5-12(23-2)16-18(14)28-8-26-16/h4-5,20H,6-8H2,1-3H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C19H18O9
Molecular Weight	390.34
AlogP	2.11
Hydrogen Bond Acceptor	9.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	101.91
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	28.0

Assay Description	Organism	Bioactivity	Reference
Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced toxicity at 0.1 mM by MTT method relative to control	Rattus norvegicus	27.4 %
Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced cytotoxicity at 10 uM after 1 hrs by MTT assay relative to control treated before D-galactosamine challenge	Rattus norvegicus	11.2 %
Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced cytotoxicity at 100 uM treated 1 hr before D-galactosamine challenge after 24 hrs by MTT assay	Rattus norvegicus	47.0 %
Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of D-galactosamine-induced cell damage at 10 uM treated 1 hr before D-galactosamine challenge after 24 hrs by MTT assay	Rattus norvegicus	67.0 %
Hepatoprotective activity in rat WB-F344 cells assessed as inhibition of DL-Galactosamine-induced toxicity at 10 uM incubated for 1 hr prior to DL-Galactosamine-challenge measured after 24 hrs by MTT assay	Rattus norvegicus	42.0 %
Hepatoprotective activity in human HL7702 cells assessed as inhibition of D-galactosamine-induced cell damage at 10 uM preincubated for 1 hr prior to D-galactosamine challenge measured after 24 hrs by MTT assay relative to untreated control	Homo sapiens	16.7 %
Hepatoprotective activity in human HL-7702 cells assessed as inhibition of D-galactosamine-induced cell toxicity incubated for 1 hr prior to D-galactosamine-challenge measured after 24 hrs by MTT assay relative to control	Homo sapiens	42.5 %
Hepatoprotective activity in human HL-7702 cells assessed as inhibition of D-galactosamine-induced toxicity at 1x10'-5 M by MTT assay relative to control	Homo sapiens	29.4 %
Hepatoprotective activity in human HepG2 cells assessed as inhibition of paracetamol-induced cell damage at 10 uM preincubated for 1 hr followed by paracetamol addition measured after 24 hrs by MTT assay relative to control	Homo sapiens	19.5 %
Hepatoprotective activity in human HepG2 cells assessed as inhibition of paracetamol-induced reduction in cell viability at 10 uM pretreated for 1 hr followed by paracetamol addition after 24 hrs by MTT assay relative to control	Homo sapiens	28.28 %
Hepatoprotective activity in human HepG2 cells assessed as inhibition of paracetamol-induced reduction in cell viability at 10 uM pretreated for 1 hr followed by paracetamol addition after 24 hrs by MTT assay relative to control	Homo sapiens	52.6 %
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	8.5 %
Hepatoprotective activity in human HepG2 cells assessed as inhibition of APAP-induced cell damage at 10 uM by MTT assay relative to control	Homo sapiens	15.7 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	5.868 %
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 %

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL482035
DrugBank	DB16014
FDA SRS	9734122TH2
PubChem	9821754
SureChEMBL	SCHEMBL9600725
ZINC	ZINC000002012988

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).