Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H22O9 |
| Molecular Weight | 346.3298 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C=CO[C@@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@]1([H])C(CO)=C[C@H]2O
InChI
InChIKey=RJWJHRPNHPHBRN-FKVJWERZSA-N
InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25576403
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25576403
Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Aucubin has been shown to exhibit anti-proliferative and apoptotic functions. Aucubin has shown effectiveness as antifungal and suggests its promising potential use as solution for C. albicans biofilm-related infections. Aucubin has a range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL392 |
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Target ID: CHEMBL366 |
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Target ID: CHEMBL5318 |
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Target ID: CHEMBL613497 |
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Target ID: CHEMBL367 |
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| 9.2 µM [IC50] | |||
Target ID: CHEMBL230 |
8.83 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Curative | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique. | 2001 Aug |
|
| Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. | 2003 Jul |
|
| Iridoid and bisiridoid glycosides from Globularia cordifolia. | 2003 May-Jun |
|
| Earthworms and litter distribution affect plant-defensive chemistry. | 2004 Apr |
|
| Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts. | 2005 Jul |
|
| Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin. | 2005 May |
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| Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues. | 2007 Jan |
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| Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides. | 2007 Jan 29 |
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| Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds. | 2007 Jun |
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| Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana. | 2007 May |
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| The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues. | 2008 Jan 22 |
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| A new iridoid glycoside from Scrophularia ningpoensis. | 2009 |
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| Iridoids from Euphrasia genargentea, a rare Sardinian endemism. | 2009 |
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| [Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides]. | 2009 Aug |
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| Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds. | 2009 Aug |
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| Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide. | 2009 Jan-Feb |
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| Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour. | 2009 Jan-Feb |
|
| Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L. | 2009 Jun |
|
| Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study. | 2009 Nov 1 |
|
| X-ray crystal structure of iridoid glucoside aucubin and its aglycone. | 2009 Nov 2 |
|
| Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity. | 2010 |
|
| Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. | 2010 Dec 13 |
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| [The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach]. | 2010 Oct-Dec |
|
| Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
Patents
Sample Use Guides
Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.
Route of Administration:
Intraperitoneal
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207-540-8
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407293
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M2138
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91458
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2G52GS8UML
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C006650
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AUCUBIN
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479-98-1
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DTXSID60963965
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SUBSTANCE RECORD
