5-METHOXY-2,2-DIMETHYL-6-(2-METHYL-1-OXO-2-BUTENYL)-10-PROPYL-2H,8H-BENZO[1,2-B

/static/temp/default.svg

Search structure


Source	Gaulton A, Kale N, van Westen GJ, Bellis LJ, Bento AP, Davies M, Hersey A, Papadatos G, Forster M, Wege P, Overington JP. A large-scale crop protection bioassay data set. Sci Data. 2015 Jul 7;2:150032. Read more ...


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

Structure


InChI Key	RMUWCAYGHBNRQJ-MDWZMJQESA-N
Smiles	CCCC1=CC(=O)Oc2c(C(=O)\C(=C\C)\C)c(OC)c3C=CC(C)(C)Oc3c12
InChI	InChI=1S/C23H26O5/c1-7-9-14-12-16(24)27-22-17(14)21-15(10-11-23(4,5)28-21)20(26-6)18(22)19(25)13(3)8-2/h8,10-12H,7,9H2,1-6H3/b13-8+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C23H26O5
Molecular Weight	382.45
AlogP	5.32
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	5.0
Polar Surface Area	61.83
Molecular species	None
Aromatic Rings	1.0
Heavy Atoms	28.0

Assay Description	Organism	Bioactivity	Reference
Selectivity index, ratio of IC50 for human MOLT4 cells to EC50 for X4 tropic HIV1 NL4-3 infected in human Molt4 cells	None	2.93
Selectivity index, ratio of IC50 for PMA-stimulated human U1 cells to EC50 for X4 tropic HIV1 NL4-3 infected in PMA-stimulated human U1 cells	None	2.43
Selectivity index, ratio of IC50 for TNF-alpha-stimulated human U1 cells to EC50 for X4 tropic HIV1 NL4-3 infected in TNF-alpha-stimulated human U1 cells	None	1.95
Cytotoxicity against Homo sapiens (human) TZM-bl cells by MTT assay	Homo sapiens	10000.0 nM
Cytotoxicity against Homo sapiens (human) MOLT4 cells by MTT assay	Homo sapiens	10000.0 nM
Cytotoxicity against Homo sapiens (human) U1 cells by MTT assay in presence of TNF-alpha	Homo sapiens	8440.0 nM
Cytotoxicity against Homo sapiens (human) U1 cells by MTT assay in presence of PMA	Homo sapiens	8440.0 nM
Inhibition of NF-kappa B p65 activity in TNFalpha-treated Homo sapiens (human) U1 cells at 10 uM after 2 to 4 hr by luciferase assay	Homo sapiens	None
Reduction in NF-kappa B p65 cytosolic level in TNFalpha-treated Homo sapiens (human) U1 cells after 0.5 to 6 hr by Western blot analysis	Homo sapiens	None
Inhibition of NF-kappa B p65 nuclear translocation in TNFalpha-treated Homo sapiens (human) U1 cells after 0.5 to 6 hr by Western blot analysis	Homo sapiens	None
Binding affinity to NF-kappa B p65 in Homo sapiens (human) U1 nuclear extract after 0.5 to 4 hr by competitive EMSA	Homo sapiens	None
Inhibition of NF-kappaB-mediated viral replication in Homo sapiens (human) Molt-4 cells infected with X4 tropic HIV1 NL4-3 at 10 uM after 24 hr by RT-PCR analysis	Homo sapiens	None
Inhibition of NF-kappaB-mediated viral replication in Homo sapiens (human) U1 cells infected with X4 tropic HIV1 NL4-3 at 10 uM after 24 hr by RT-PCR analysis in presence of TNF-alpha	Homo sapiens	None
Inhibition of NF-kappaB-mediated viral replication in Homo sapiens (human) TZM-bl cells infected with X4 tropic HIV1 NL4-3 compound pre-treated for 2hr before infection measured after 24 hr by luciferase assay	Homo sapiens	None
Antiviral activity against X4 tropic Human immunodeficiency virus 1 NL4-3 infected human Molt4 cells assessed as intracellular p24 expression at 10 uM after 7 days by flow cytometry	Human immunodeficiency virus 1	None
Antiviral activity against X4 tropic Human immunodeficiency virus 1 NL4-3 infected human Molt4 cells assessed as intracellular p24 expression after 4 to 7 days by flow cytometry	Human immunodeficiency virus 1	3410.0 nM
Antiviral activity against X4 tropic Human immunodeficiency virus 1 NL4-3 infected human Molt4 cells assessed as intracellular p24 expression at 10 uM after 4 days by flow cytometry	Human immunodeficiency virus 1	None
Antiviral activity against Human immunodeficiency virus 1 infected U1 cells assessed as intracellular p24 expression after 24 hr by flow cytometry in presence of TNF-alpha	Human immunodeficiency virus 1	None		Antiviral activity against Human immunodeficiency virus 1 infected U1 cells assessed as intracellular p24 expression after 24 hr by flow cytometry in presence of TNF-alpha	Human immunodeficiency virus 1	4320.0 nM
Antiviral activity against Human immunodeficiency virus 1 infected U1 cells assessed as intracellular p24 expression after 24 hr by flow cytometry in presence of PMA	Human immunodeficiency virus 1	None		Antiviral activity against Human immunodeficiency virus 1 infected U1 cells assessed as intracellular p24 expression after 24 hr by flow cytometry in presence of PMA	Human immunodeficiency virus 1	3480.0 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL478978

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).