((4S,4AS,5S,8AS)-8A-HYDROXY-3,4A,5-TRIMETHYL-4,4A,5,6,7,8,8A,9-OCTAHYDRONAPHTHO[2,3-B]FURAN-4-YL)2-METHYLBUT-2-ENOATE

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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	WPNXICJHRZQRMC-HUVTZIOQSA-N
Smiles	C\C=C(\C)/C(=O)O[C@@H]1c2c(C)coc2C[C@@]3(O)CCC[C@H](C)[C@@]13C
InChI	InChI=1S/C20H28O4/c1-6-12(2)18(21)24-17-16-13(3)11-23-15(16)10-20(22)9-7-8-14(4)19(17,20)5/h6,11,14,17,22H,7-10H2,1-5H3/b12-6-/t14-,17+,19-,20-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H28O4
Molecular Weight	332.43
AlogP	4.32
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	3.0
Polar Surface Area	59.67
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	24.0

Assay Description	Organism	Bioactivity	Reference
Antitermite activity against greater than third-instar stage of Coptotermes formosanus workers/1 soldier in compound-pretreated filter paper assessed as filter paper consumption at 0.5% at 26 degC after 21 days (Rvb = 41.4 +/-5.6 mg)	Coptotermes formosanus	16.5 mg
Antitermite activity against greater than third-instar stage of Coptotermes formosanus workers/1 soldier in compound-pretreated filter paper assessed as mortality at 0.5% at 26 degC after 21 days (Rvb = 3.8 +/-4.8%)	Coptotermes formosanus	18.8 %
Antitermite activity against greater than third-instar stage of Coptotermes formosanus workers/1 soldier in compound-pretreated filter paper assessed as mortality at 0.5% at 26 degC after 13 days (Rvb = 3.8 +/-4.8%)	Coptotermes formosanus	16.3 %
Antitermite activity against greater than third-instar stage of Coptotermes formosanus workers/1 soldier in compound-pretreated filter paper assessed as mortality at 0.5% at 26 degC after 6 days (Rvb = 2.5 +/-5%)	Coptotermes formosanus	3.8 %
Antitermite activity against greater than third-instar stage of Coptotermes formosanus workers/1 soldier in compound-pretreated filter paper assessed as mortality at 0.5% at 26 degC after 1 day (Rvb = 0%)	Coptotermes formosanus	1.3 %
Inhibition of photosynthetic electron transport rate in Cucumis sativa Straight Eight (cucumber) cotyledons assessed as chlorophyll fluorescence at 100 uM at 22 degC measured at 2 to 24 hr post-drug treatment under constant light by fluorometer analysis	Cucumis sativus	None
Induction of cell membrane integrity disruption in Cucumis sativus (cucumber) cotyledons assessed as electrolyte leakage at 25 degC by conductivity meter analysis	Cucumis sativus	None
Inhibition of mitotic cell division in Allium cepa cv. Evergreen (onion) root tips assessed as cell count at telophase stage of cell cycle at 100 to 300 uM at 24 degC	Allium cepa	None
Inhibition of mitotic cell division in Allium cepa cv. Evergreen (onion) root tips assessed as cell count at anaphase stage of cell cycle at 100 to 300 uM at 24 degC	Allium cepa	None
Inhibition of mitotic cell division in Allium cepa cv. Evergreen (onion) root tips assessed as cell count at metaphase stage of cell cycle at 100 to 300 uM at 24 degC	Allium cepa	None
Inhibition of mitotic cell division in Allium cepa cv. Evergreen (onion) root tips assessed as cell count at prophase stage of cell cycle at 100 to 300 uM at 24 degC	Allium cepa	None
Phytotoxic activity against three-frond Lemna paucicostata colonies assessed as growth inhibition after 4 days	Lemna paucicostata	2940.0 nM
Phytotoxic activity against Lactuca sativa (lettuce) seeds assessed as inhibition of germination at 1 uM at 26 degC measured 7 days post-drug dose	Lactuca sativa	None
Phytotoxic activity against Lactuca sativa (lettuce) seeds assessed as inhibition of germination at 100 uM at 26 degC measured 7 days post-drug dose	Lactuca sativa	None
Phytotoxic activity against Lactuca sativa (lettuce) seeds assessed as inhibition of germination at 10 uM at 26 degC measured 7 days post-drug dose	Lactuca sativa	None
Phytotoxic activity against Agrostis stolonifera seeds assessed as inhibition of germination at 1 uM at 26 degC measured 12 days post-drug dose	Agrostis stolonifera	None
Phytotoxic activity against Agrostis stolonifera seeds assessed as inhibition of germination at 10 uM at 26 degC measured 12 days post-drug dose	Agrostis stolonifera	None

Cross References

Resources	Reference
ChEMBL	CHEMBL2252624
PubChem	76319166

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).