Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H11NO3 |
Molecular Weight | 253.2527 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(=CC=C1)C2=C(O)C(=O)NC3=CC=CC=C23
InChI
InChIKey=QIJIOTTYIGBOQA-UHFFFAOYSA-N
InChI=1S/C15H11NO3/c17-10-5-3-4-9(8-10)13-11-6-1-2-7-12(11)16-15(19)14(13)18/h1-8,17-18H,(H,16,19)
Molecular Formula | C15H11NO3 |
Molecular Weight | 253.2527 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Viridicatol is a polar metabolite first isolated from Penicillium cyclopium and P. viridicatum by Birkinshaw and collaborators in
1963. Viridicatol is a 2,3-dihydroxyquinoline which, like its analogue viridicatin, exists in equilibrium with its keto-tautomer.
Viridicatol acts as an anti-inflammatory agent by suppressing the expression of pro-inflammatory mediators such as inducible
nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2, via inhibition of the nuclear factor-kappa B (NF-κB) pathway in
LPS stimulated cells. Further, viridicatol is a selective inhibitor of PTP1B, a potential drug target for the treatment of type 2
diabetes and obesity. Viridicatol revealed potent antibacterial activity against Staphylococcus aureus.
Originator
Sources: http://www.bioaustralis.com/pdfs/BIA-V1681-DS.pdf
Curator's Comment: Viridicatol is a polar metabolite first isolated from Penicillium cyclopium and P. viridicatum by Birkinshaw and collaborators in 1963.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27910702 |
|||
Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23770564 |
64.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS. 114. VIRIDICATOL AND CYCLOPENOL, METABOLITES OF PENICILLIUM VIRIDICATUM WESTLING AND PENICILLIUM CYCLOPIUM WESTLING. | 1963 Nov |
|
PTP1B inhibitory secondary metabolites from marine-derived fungal strains Penicillium spp. and Eurotium sp. | 2013 Sep 28 |
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A new isoquinolone alkaloid from an endophytic fungus R22 of Nerium indicum. | 2017 Apr |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23770564
Viridicatol inhibited PTP1B activity in a dose-dependent manner with IC50 value of 64.0 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:46:29 GMT 2023
by
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Fri Dec 15 19:46:29 GMT 2023
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Record UNII |
45P12JNE0L
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Record Status |
Validated (UNII)
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Record Version |
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