SULFORAPHANE

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Search structure


Synonyms	(-)-sulforaphane (r)-sulforaphane 4-(Methylsulfinyl)Butyl Isothiocyanate Sulforaphane Sulforaphane, (r)-
Status
Molecule Category	UNKNOWN
UNII	41684WL1GL
EPA CompTox	DTXSID8036732


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

Structure


InChI Key	SUVMJBTUFCVSAD-UHFFFAOYSA-N
Smiles	C[S+]([O-])CCCCN=C=S
InChI	InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C6H11NOS2
Molecular Weight	177.29
AlogP	1.25
Hydrogen Bond Acceptor	3.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	5.0
Polar Surface Area	29.43
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	10.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of 7,12-dimethylbenz[a]anthracene-induced periplastic lesions in mouse mammary organ culture model at 1 ug/ml	Mus musculus	83.7 %
Inhibition of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary gland culture at 1 ug/mL	Mus musculus	83.7 %
Inhibition of mouse Hepa-1c1c7 cells assessed as cell viability	Mus musculus	2.1 ug.mL-1
Cytotoxicity against mouse Hepa-1c1c7 cells	Mus musculus	2.07 ug.mL-1
Antibacterial activity against Pseudomonas aeruginosa PAO1 assessed as inhibition of pyocyanin production at 100 uM after 20 hrs	Pseudomonas aeruginosa PAO1	70.0 %
Inhibition of iNOS in LPS-stimulated mouse RAW264.7 cells assessed as inhibition of nitric oxide production after 48 hrs by Griess assay	Mus musculus	400.0 nM
Inhibition of EGFR-TK in human A431 cell lysate assessed as reduction in EGF stimulated kinase activity at highest concentration after 60 mins using biotinylated peptide substrate by ELISA analysis	Homo sapiens	69.0 %
Antagonist activity at Pseudomonas aeruginosa PAO1 GFP-fused RhlR expressed in Escherichia coli DH5alpha co-expressing rhlA promoter assessed as inhibition of L-arabinose-induced C4-HSL production at 2.27 mM after 5 hrs relative to control	Pseudomonas aeruginosa	42.06 %
Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation at 16 uM after 72 hrs by CCK8 assay	Homo sapiens	54.05 %
Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation at 32 uM after 72 hrs by CCK8 assay	Homo sapiens	77.35 %
Antiproliferative activity against human SMMC7721 cells assessed as inhibition of cell proliferation at 16 uM after 72 hrs by CCK8 assay	Homo sapiens	80.54 %
Antiproliferative activity against human SMMC7721 cells assessed as inhibition of cell proliferation at 32 uM after 72 hrs by CCK8 assay	Homo sapiens	88.32 %
Activation of ED-tagged Nrf2 in human U2OS cells co-expressing Keap1 assessed as induction of NRF2 translocation to nucleus after 6 hrs by beta-galactosidase based chemiluminescent assay	Homo sapiens	580.0 nM
Activation of NRF2 in human U2OS cells co-expressing Keap1 (unknown origin) assessed as induction of NRF2 translocation to nucleus incubated for 6 hrs by beta-galactosidase based chemiluminescent assay	Homo sapiens	870.0 nM
Activation of NRF2 in human U2OS cells co-expressing Keap1 assessed as induction of NRF2 translocation to nucleus after 6 hrs by beta-galactosidase based chemiluminescent assay	Homo sapiens	580.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	47807
ChEMBL	CHEMBL48802
FDA SRS	41684WL1GL
Human Metabolome Database	HMDB0005792
Guide to Pharmacology	6569
PubChem	9577379
SureChEMBL	SCHEMBL105202

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).