BIO101   Click here for help

GtoPdb Ligand ID: 11987

Synonyms: 20-Hydroxyecdysone | beta-Ecdysone | Crustecdysone | Ecdysterone | Sarconeos
PDB Ligand
Compound class: Natural product
Comment: BIO101 is pharmaceutical grade 20-hydroxyecdysone, the latter being a natural product found in the Asparagus filicinus fern, the trematode Trichobilharzia ocellata, and other organisms. Its activity as a non-peptidic activator of the class A orphan GPCR MAS1 has been proposed to offer potential clinical utility to counteract dysregulation of the renin-angiotensin system (RAS) in patients with COVID-19 respiratory failure [1-2]. Given the role of ACE2 in the RAS, and the disturbance of ACE2 function that likely ensues when SARS-CoV-2 spike protein binds to ACE2, it is feasible that the RAS will be dysregulated in COVID-19, and that ameliorating this disruption through targeted pharmacological intervention might be of potential clinical benefit.
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 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.

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Hydrogen bond acceptors 7
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 138.45
Molecular weight 480.31
XLogP 1.05
No. Lipinski's rules broken 1
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.

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Canonical SMILES O[C@H]1C[C@@]2(C)[C@@H](C[C@H]1O)C(=O)C=C1[C@@H]2CC[C@]2([C@@]1(O)CC[C@@H]2[C@]([C@@H](CCC(O)(C)C)O)(O)C)C
Isomeric SMILES C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O
InChI InChI=1S/C27H44O7/c1-23(2,32)9-8-22(31)26(5,33)21-7-11-27(34)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-34H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22+,24+,25+,26+,27+/m0/s1
InChI Key NKDFYOWSKOHCCO-YPVLXUMRSA-N
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Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel