Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H14O5 |
| Molecular Weight | 322.3115 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C(=C1/OC(=O)C(=C1O)C2=CC=CC=C2)\C3=CC=CC=C3
InChI
InChIKey=OMZRMXULWNMRAE-ICFOKQHNSA-N
InChI=1S/C19H14O5/c1-23-18(21)15(13-10-6-3-7-11-13)17-16(20)14(19(22)24-17)12-8-4-2-5-9-12/h2-11,20H,1H3/b17-15-
| Molecular Formula | C19H14O5 |
| Molecular Weight | 322.3115 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Vulpinic Acid is a lichen metabolite with anti-inflammatory properties. Vulpinic Acid acts as photoprotective agent and antifungal agent. Vulpinic acid mainly affects cell cycle, glycogen metabolism, transcription and translation to fungi. Vulpinic acid showed very strong inhibition effect on TrxR (mitochondrial thioredoxin reductase), so it may be used as a potential drug for cancer therapy. Vulpinic acid possesses diverse biological activities, and lichens containing Vulpinic acid have a strong history of medicinal use. For example, Eskimos and people of Northern Europe have used lichens containing Vulpinic acid to poison the wolf and fox.Lichens containing Vulpinic acid are used as fodder for reindeer and emergency food by Arctic and Subarctic peoples. In central Europe, members of the genus Cetraria, which is known to produce Vulpinic acid, have been used as laxatives and have been taken for coughing, including that associated with tuberculosis.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5086 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27141875 |
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Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25919857 |
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Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12542354 |
218.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The inherent matrix properties of lichen metabolites in matrix-assisted laser desorption ionization time-of-flight mass spectrometry. | 2017-12-15 |
|
| Specialized Metabolites of the Lichen Vulpicida pinastri Act as Photoprotective Agents. | 2017-07-12 |
|
| Chemical and biological investigation of the fungus Pulveroboletus ravenelii. | 2003-01 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12542354
Vulpinic acid and its polymorph showed strong in vitro activity against S. aureus, having IC50 values of <2 ug/mL. Vulpinic acid showed weak activity against COX-1 with IC50 value of 218 uM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:55:34 GMT 2025
by
admin
on
Mon Mar 31 19:55:34 GMT 2025
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| Record UNII |
13N7RF6M84
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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VULPINIC ACID
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DTXSID601027308
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208-314-1
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521-52-8
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13N7RF6M84
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5897
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54699186
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