U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of VULPINIC ACID

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-

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Chemical and biological investigation of the fungus Pulveroboletus ravenelii.
2003 Jan
The inherent matrix properties of lichen metabolites in matrix-assisted laser desorption ionization time-of-flight mass spectrometry.
2017 Dec 15
Specialized Metabolites of the Lichen Vulpicida pinastri Act as Photoprotective Agents.
2017 Jul 12
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Fri Dec 15 19:44:27 GMT 2023
Edited
by admin
on Fri Dec 15 19:44:27 GMT 2023
Record UNII
13N7RF6M84
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VULPINIC ACID
Common Name English
METHYL (2E)-2-(5-HYDROXY-3-OXO-4-PHENYLFURAN-2-YLIDENE)-2-PHENYLACETATE
Systematic Name English
NSC-5897
Code English
Code System Code Type Description
WIKIPEDIA
VULPINIC ACID
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID601027308
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-314-1
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY
CAS
521-52-8
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY
FDA UNII
13N7RF6M84
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY
NSC
5897
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY
PUBCHEM
54699186
Created by admin on Fri Dec 15 19:44:27 GMT 2023 , Edited by admin on Fri Dec 15 19:44:27 GMT 2023
PRIMARY