sulforaphane   Click here for help

GtoPdb Ligand ID: 6569

Compound class: Natural product
Comment: Found in cruciferous vegetables such as brocolli. It has potential chemopreventive [1], anti-cancer [5] and neuroprotective actions [4]. It may act as a quinone reductase inducer [3]. Potential to modulate lipid dysregulation in obesity-related diseases is suggested by sulforaphane-mediated inhibition of the sterol regulatory element-binding protein (SREBs) transcription factors which regulate the expression of genes that are involved in fatty acid and cholesterol biosynthesis [2].

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 80.73
Molecular weight 177.03
XLogP 1.18
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES S=C=NCCCCS(=O)C
Isomeric SMILES S=C=NCCCCS(=O)C
InChI InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
InChI Key SUVMJBTUFCVSAD-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
1-isothiocyanato-4-methylsulfinylbutane
Database Links Click here for help
CAS Registry No. 4478-93-7 (source: Scifinder)
ChEBI CHEBI:47807
GtoPdb PubChem SID 178103183
PubChem CID 5350
Search Google for chemical match using the InChIKey SUVMJBTUFCVSAD-UHFFFAOYSA-N
Search Google for chemicals with the same backbone SUVMJBTUFCVSAD
UniChem Compound Search for chemical match using the InChIKey SUVMJBTUFCVSAD-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey SUVMJBTUFCVSAD-UHFFFAOYSA-N
Wikipedia Sulforaphane

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MedChemExpress
Sulforaphane (links to external site)
Cat. No. HY-13755