RETRORSINE

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Search structure


Synonyms	Retrorsine
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	BCJMNZRQJAVDLD-FXGRWVCYSA-N
Smiles	C\C=C\1/C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23
InChI	InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H25NO6
Molecular Weight	351.39
AlogP	0.92
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	1.0
Polar Surface Area	96.3
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	25.0

Assay Description	Organism	Bioactivity	Reference
Phytotoxicity against Lactuca sativa var. Carrascoy (lettuce) assessed as inhibition of radicle length at 50 ug/cm2 after 24 to 144 hr	Lactuca sativa	50.0 %		Phytotoxicity against Lactuca sativa var. Carrascoy (lettuce) assessed as inhibition of radicle length at 50 ug/cm2 after 24 to 144 hr	Lactuca sativa	50.0 %
Toxicity against Cricetulus griseus CHO (Chinese hamster ovary) cell by MTT assay	Cricetulus griseus	100.0 ug.mL-1		Toxicity against Cricetulus griseus CHO (Chinese hamster ovary) cell by MTT assay	Cricetulus griseus	100.0 ug.mL-1
Phytotoxicity against Lactuca sativa var. Carrascoy (lettuce) assessed as inhibition of seed germination at 50 ug/cm2 after 24 hr	Lactuca sativa	None		Phytotoxicity against Lactuca sativa var. Carrascoy (lettuce) assessed as inhibition of seed germination at 50 ug/cm2 after 24 hr	Lactuca sativa	None
Toxicity against Spodoptera frugiperda (fall armyworm) Sf9 cells by MTT assay	Spodoptera frugiperda	100.0 ug.mL-1		Toxicity against Spodoptera frugiperda (fall armyworm) Sf9 cells by MTT assay	Spodoptera frugiperda	100.0 ug.mL-1
Antifeedant activity against Spodoptera littoralis L6 larvae assessed as biomass gain orally dosed with 40 ug after 72 hr relative to untreated control	Spodoptera littoralis	102.0 %		Antifeedant activity against Spodoptera littoralis L6 larvae assessed as biomass gain orally dosed with 40 ug after 72 hr relative to untreated control	Spodoptera littoralis	90.0 %
Antifeedant activity against Spodoptera littoralis L6 larvae assessed as food consumption level orally dosed with 40 ug after 72 hr relative to untreated control	Spodoptera littoralis	92.0 %		Antifeedant activity against Spodoptera littoralis L6 larvae assessed as food consumption level orally dosed with 40 ug after 72 hr relative to untreated control	Spodoptera littoralis	88.0 %
Antifeedant activity against Rhopalosiphum padi adults fed on compound treated Hordeum vulgare annuum leaves assessed as feeding level at 50 ug/cm2 (Rvb = 47 to 64%)	Rhopalosiphum padi	40.0 %		Antifeedant activity against Rhopalosiphum padi adults fed on compound treated Hordeum vulgare annuum leaves assessed as feeding level at 50 ug/cm2 (Rvb = 47 to 64%)	Rhopalosiphum padi	46.0 %
Antifeedant activity against Myzus persicae (green peach aphid) adults fed on compound treated Hordeum vulgare annuum leaves assessed as feeding level at 50 ug/cm2 (Rvb = 43 to 70%)	Myzus persicae	30.0 %		Antifeedant activity against Myzus persicae (green peach aphid) adults fed on compound treated Hordeum vulgare annuum leaves assessed as feeding level at 50 ug/cm2 (Rvb = 43 to 70%)	Myzus persicae	44.0 %
Antifeedant activity against Leptinotarsa decemlineata adults fed on compound treated Capsicum annuum leaves assessed as inhibition of feeding	Leptinotarsa decemlineata	None		Antifeedant activity against Leptinotarsa decemlineata adults fed on compound treated Capsicum annuum leaves assessed as inhibition of feeding	Leptinotarsa decemlineata	50.0 microg/cm2
Antifeedant activity against Spodoptera littoralis sixth-instar larvae fed on compound treated Solanum tuberosum leaves assessed as inhibition of feeding	Spodoptera littoralis	None		Antifeedant activity against Spodoptera littoralis sixth-instar larvae fed on compound treated Solanum tuberosum leaves assessed as inhibition of feeding	Spodoptera littoralis	50.0 microg/cm2

Cross References

Resources	Reference
ChEMBL	CHEMBL520570
PubChem	5281756

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).