BETA-HYDROXYISOVALERYLSHIKONIN


Synonyms	3'-Hydroxyisovalerylshikonin Beta-Hydroxyisovalerylshikonin
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	MXANJRGHSFELEJ-MRXNPFEDSA-N
Smiles	CC(=CC[C@@H](OC(=O)CC(C)(C)O)C1=CC(=O)c2c(O)ccc(O)c2C1=O)C
InChI	InChI=1S/C21H24O7/c1-11(2)5-8-16(28-17(25)10-21(3,4)27)12-9-15(24)18-13(22)6-7-14(23)19(18)20(12)26/h5-7,9,16,22-23,27H,8,10H2,1-4H3/t16-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H24O7
Molecular Weight	388.41
AlogP	2.98
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	7.0
Polar Surface Area	121.13
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	28.0

Assay Description	Organism	Bioactivity
Phytotoxicity against Nicotiana tabacum (tobacco) plant at 25 mM	Nicotiana tabacum	None
Antifungal activity against Cladosporium herbarum assessed as inhibition at 10 nmol in 8 mm disk	Cladosporium herbarum	9.1 mm
Antifungal activity against Cladosporium herbarum assessed as inhibition at 250 nmol in 8 mm disk	Cladosporium herbarum	16.0 mm
Antifungal activity against Cladosporium herbarum assessed as inhibition at 50 nmol in 8 mm disk	Cladosporium herbarum	13.8 mm
Antifungal activity against Cladosporium herbarum assessed as inhibition at 1250 nmol in 8 mm disk	Cladosporium herbarum	17.6 mm
Antiviral activity against Tobacco mosaic virus (TMV) in compound treated tobacco leaf assessed as growth inhibition at 5 mM at 25 degC for 3 days (16 hr in light) by half-leaf method	Tobacco mosaic virus	44.0 %

Cross References

Resources	Reference
ChEMBL	CHEMBL397309
PubChem	479502
SureChEMBL	SCHEMBL842120

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).

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).