scutellarin   Click here for help

GtoPdb Ligand ID: 13075

Synonyms: breviscapin | scutellarein-7-glucuronide
Compound class: Natural product
Comment: Scutellarin is a bioactive plant-derived flavinoid compound that has been isolated from plants including Scoparia dulcis (sweet broom), Sempervivum ruthenicum (houseleek), the daisy-like plant Erigeron breviscapus and Scutellaria species (skullcaps). It has been used as a traditional herbal remedy, and has more recently been investigated for actions that support anti-cancer potential [3-5]. Integrated network pharmacology predictive analysis followed by experimental validation suggests that the c-Jun N-terminal kinases (JNK) pathway is important for scutellarin's bioactivity in acute myeloid leukemia (AML) models [1].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 12
Hydrogen bond donors 7
Rotatable bonds 4
Topological polar surface area 203.44
Molecular weight 462.36
XLogP 0.07
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C(=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O4)O)O)O)O2)O
Isomeric SMILES C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O)O
InChI InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChI Key DJSISFGPUUYILV-ZFORQUDYSA-N
Classification Click here for help
Compound class Natural product
IUPAC Name Click here for help
(2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms Click here for help
breviscapin | scutellarein-7-glucuronide
Database Links Click here for help
BindingDB Ligand 50242284
ChEBI CHEBI:61278
ChEMBL Ligand CHEMBL487805
GtoPdb PubChem SID 491299857
LIPID MAPS LMPK12111110
PubChem CID 185617
Search Google for chemical match using the InChIKey DJSISFGPUUYILV-ZFORQUDYSA-N
Search Google for chemicals with the same backbone DJSISFGPUUYILV
UniChem Compound Search for chemical match using the InChIKey DJSISFGPUUYILV-ZFORQUDYSA-N
UniChem Connectivity Search for chemical match using the InChIKey DJSISFGPUUYILV-ZFORQUDYSA-N