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sinigrin   Click here for help

GtoPdb Ligand ID: 12456

Synonyms: Myronate | Myronic acid
PDB Ligand
Compound class: Natural product
Comment: Sinigrin is a naturaly occurring compound that is present in the Brassicaceae family plants Cakile arabica and Erucaria cakiloidea.
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 8
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 199.79
Molecular weight 359.38
XLogP -1.84
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 C=CC/C(=N\OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Isomeric SMILES C=CC/C(=N\OS(=O)(=O)O)/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
InChI InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/b11-6+/t5-,7-,8+,9-,10+/m1/s1
InChI Key PHZOWSSBXJXFOR-PTGZALFTSA-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
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1E)-N-sulfooxybut-3-enimidothioate
Synonyms Click here for help
Myronate | Myronic acid
Database Links Click here for help
Specialist databases
GPCRdb Ligand sinigrin
Other databases
GtoPdb PubChem SID 479821246
PubChem CID 6911854
RCSB PDB Ligand SZZ
Search Google for chemical match using the InChIKey PHZOWSSBXJXFOR-PTGZALFTSA-N
Search Google for chemicals with the same backbone PHZOWSSBXJXFOR
UniChem Compound Search for chemical match using the InChIKey PHZOWSSBXJXFOR-PTGZALFTSA-N
UniChem Connectivity Search for chemical match using the InChIKey PHZOWSSBXJXFOR-PTGZALFTSA-N