VIRIDICATOL

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

Structure Search

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)

HIDE SMILES / InChI

Description
Sources: http://www.bioaustralis.com/pdfs/BIA-V1681-DS.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27910702 | https://www.ncbi.nlm.nih.gov/pubmed/23770564

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27910702	Inhibitor 8297
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23770564	Inhibitor 8297		64.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23770564	Primary		Basic research	Unknown Approved Use Unknown

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	14084602
[On the synthesis of quinoline alkaloids in plants. 2. Fermentativ conversion of the penicillin alkaloids cyclopenin and cyclopenol to viridicatin and viridicatol].	1967 Jul	6079765
PTP1B inhibitory secondary metabolites from marine-derived fungal strains Penicillium spp. and Eurotium sp.	2013 Sep 28	23770564
A new isoquinolone alkaloid from an endophytic fungus R22 of Nerium indicum.	2017 Apr	27910702

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Viridicatol inhibited PTP1B activity in a dose-dependent manner with IC50 value of 64.0 uM.

Name

Type

Language

VIRIDICATOL

Common Name

English

2(1H)-QUINOLINONE, 3-HYDROXY-4-(3-HYDROXYPHENYL)-

Systematic Name

English

CARBOSTYRIL, 3-HYDROXY-4-(M-HYDROXYPHENYL)-

Systematic Name

English

Code System Code Type Description

CAS

14484-44-7