Chemicals and Drugs

Glaucarubin

(1 beta,2 alpha,11 beta,12 alpha,15 beta(S))-11,20-Epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one. A quassinoid (Simaroubolide) from Simaruba glauca, a tropical shrub. It has been used as an antiamebic agent and is found to be cytotoxic. It may be of use in cancer chemotherapy.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

(1 beta,2 alpha,11 beta,12 alpha,15 beta(S))-11,20-Epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one. A quassinoid (Simaroubolide) from Simaruba glauca, a tropical shrub. It has been used as an antiamebic agent and is found to be cytotoxic. It may be of use in cancer chemotherapy.

Chemical Identity

Chemical Information

Molecular Formula
C25H36O10
Molecular Weight
496.5 g/mol
CAS Registry No.
1448-23-3
IUPAC Name
[(1S,4R,5R,6R,7S,8R,11R,13S,16S,17S,18S,19R)-4,5,16,17-tetrahydroxy-6,14,18-trimethyl-9-oxo-3,10-dioxapentacyclo[9.8.0.01,7.04,19.013,18]nonadec-14-en-8-yl] (2S)-2-hydroxy-2-methylbutanoate
InChIKey
LZKVXMYVBSNXER-YZPKDWIXSA-N
SMILES
CC[C@@](C)(C(=O)O[C@@H]1[C@H]2[C@H]([C@H]([C@]3([C@H]4[C@@]2(CO3)[C@@H](C[C@@H]5[C@@]4([C@@H]([C@H](C=C5C)O)O)C)OC1=O)O)O)C)O
MeSH Unique ID
D005900
Source
PubChem CID 441794

MeSH Record

Classification

Broader headings

Related Concepts

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

1 entry terms
  • Kirondrin

MeSH Record

Aspects Covered

28 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, physiology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

91(66); was see under PHENANTHRENES 1981-90; was see under PYRANS 1975-80

MeSH Hierarchy

Tree Numbers

  1. D02w.455w.849w.919w.570w.500w
  2. D03w.383.663.387w

AMA Style

References

  1. National Library of Medicine. Glaucarubin. Medical Subject Headings (MeSH). 2026. Unique ID D005900. http://id.nlm.nih.gov/mesh/2026/D005900
  2. Glaucarubin. In: Wikipedia. https://en.wikipedia.org/wiki/Glaucarubin
  3. Glaucarubin. In: Wikidata. https://www.wikidata.org/wiki/Q27106735
  4. Glaucarubin. In: PubChem Compound. CID 441794. https://pubchem.ncbi.nlm.nih.gov/compound/441794