rosmarinic acid (racemate)   Click here for help

GtoPdb Ligand ID: 13092

Synonyms: rosmarinate
Compound class: Natural product
Comment: Rosmarinic acid is a plant-derived polyphenol that is found in a range of culinary herbs (including rosemary, sage, mint and basil). It is used as a food and beverage flavouring, and as a dietary supplement. Synthetic rosmarinic acid can be manufactured at scale. We show the chemical structure without specified stereochemistry to represent the racemic mixture of R and S enantiomers.
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 144.52
Molecular weight 360.32
XLogP 1.31
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 C1=C(/C=C/C(=O)OC(CC2=CC=C(C(=C2)O)O)C(=O)O)C=C(C(=C1)O)O
Isomeric SMILES C1=CC(=C(C=C1CC(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+
InChI Key DOUMFZQKYFQNTF-ZZXKWVIFSA-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
3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoic acid
Synonyms Click here for help
rosmarinate
Database Links Click here for help
BindingDB Ligand 50059986
ChEBI CHEBI:17226
ChEMBL Ligand CHEMBL66966
GtoPdb PubChem SID 491299874
PubChem CID 5315615
Search Google for chemical match using the InChIKey DOUMFZQKYFQNTF-ZZXKWVIFSA-N
Search Google for chemicals with the same backbone DOUMFZQKYFQNTF
UniChem Compound Search for chemical match using the InChIKey DOUMFZQKYFQNTF-ZZXKWVIFSA-N
UniChem Connectivity Search for chemical match using the InChIKey DOUMFZQKYFQNTF-ZZXKWVIFSA-N