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
OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@H]3[C@H](O)C=C(CO)[C@@H]23)[C@H](O)[C@@H](O)[C@@H]1O
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
| Molecular Formula | C15H22O9 |
| Molecular Weight | 346.3298 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|||
Target ID: CHEMBL366 |
|||
Target ID: CHEMBL5318 |
|||
Target ID: CHEMBL613497 |
|||
Target ID: CHEMBL367 |
|||
| 9.2 µM [IC50] | |||
Target ID: CHEMBL230 |
8.83 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011-12-15 |
|
| [The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach]. | 2011-05-24 |
|
| Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites. | 2011-02-16 |
|
| Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. | 2010-12-13 |
|
| [Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis]. | 2010-12 |
|
| Chungsim-Yeunja-Tang decreases the inflammatory response in peripheral blood mononuclear cells from patients with cerebral infarction through an NF-κB dependent mechanism. | 2010-11-25 |
|
| Curcumin protects intestinal mucosal barrier function of rat enteritis via activation of MKP-1 and attenuation of p38 and NF-κB activation. | 2010-09-24 |
|
| [Studies on the chemical constituents of Buddleja albiflora (II)]. | 2010-06 |
|
| A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships. | 2010-06 |
|
| Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro. | 2010-03 |
|
| Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants. | 2010-02 |
|
| Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity. | 2010 |
|
| X-ray crystal structure of iridoid glucoside aucubin and its aglycone. | 2009-11-02 |
|
| Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study. | 2009-11-01 |
|
| Free Radical Scavenging Activity of Calotropis gigantea on Streptozotocin-Induced Diabetic Rats. | 2009-11 |
|
| Chinese medicines as a resource for liver fibrosis treatment. | 2009-08-20 |
|
| [Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides]. | 2009-08 |
|
| Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds. | 2009-08 |
|
| The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L. | 2009-07 |
|
| Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory. | 2009-07 |
|
| Aucubin prevents loss of hippocampal neurons and regulates antioxidative activity in diabetic encephalopathy rats. | 2009-07 |
|
| Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L. | 2009-06 |
|
| The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. | 2009-05 |
|
| Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide. | 2009-04-23 |
|
| Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour. | 2009-03-28 |
|
| A new iridoid glycoside from Scrophularia ningpoensis. | 2009 |
|
| Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis. | 2009 |
|
| Iridoids from Euphrasia genargentea, a rare Sardinian endemism. | 2009 |
|
| Cytotoxic activities of Stachys species. | 2008-12 |
|
| A potential agent for treating non-small cell lung cancer. | 2008-09 |
|
| Oviposition cues for a specialist butterfly--plant chemistry and size. | 2008-09 |
|
| Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells. | 2008-09 |
|
| Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae). | 2008-08 |
|
| Neuroprotection of aucubin in primary diabetic encephalopathy. | 2008-06 |
|
| Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt. | 2008-04-15 |
|
| Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes. | 2008-03-17 |
|
| Effects of aucubin on the healing of oral wounds. | 2008-01-24 |
|
| The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues. | 2008-01-22 |
|
| [Research advances in pharmacology of aucubin and aucubigenin]. | 2007-12 |
|
| [Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction]. | 2007-11 |
|
| Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds. | 2007-06 |
|
| Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana. | 2007-05 |
|
| Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham. | 2007-04-04 |
|
| Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L. | 2007-03 |
|
| Overexpression of selenoprotein H reduces Ht22 neuronal cell death after UVB irradiation by preventing superoxide formation. | 2007-02-11 |
|
| Novel phytoandrogens and lipidic augmenters from Eucommia ulmoides. | 2007-01-29 |
|
| Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues. | 2007-01 |
|
| Protective actions of Rubus coreanus ethanol extract on collagenous extracellular matrix in ultraviolet-B irradiation-induced human dermal fibroblasts. | 2007 |
|
| A validation protocol for the HPTLC standardization of herbal products: application to the determination of acteoside in leaves of Plantago palmata Hook. f.s. | 2006-04-15 |
|
| Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin. | 2005-05 |
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
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 19:44:06 GMT 2025
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on
Mon Mar 31 19:44:06 GMT 2025
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| Record UNII |
2G52GS8UML
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| Record Status |
Validated (UNII)
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| Record Version |
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207-540-8
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407293
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m2138
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2G52GS8UML
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C006650
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AUCUBIN
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DTXSID60963965
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