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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 of VIRIDICATOL

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

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

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

Targets

Primary TargetPharmacologyConditionPotency
64.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
A new isoquinolone alkaloid from an endophytic fungus R22 of Nerium indicum.
2017 Apr
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Viridicatol inhibited PTP1B activity in a dose-dependent manner with IC50 value of 64.0 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:46:29 GMT 2023
Edited
by admin
on Fri Dec 15 19:46:29 GMT 2023
Record UNII
45P12JNE0L
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 19:46:29 GMT 2023 , Edited by admin on Fri Dec 15 19:46:29 GMT 2023
PRIMARY
MESH
C108793
Created by admin on Fri Dec 15 19:46:29 GMT 2023 , Edited by admin on Fri Dec 15 19:46:29 GMT 2023
PRIMARY
PUBCHEM
115033
Created by admin on Fri Dec 15 19:46:29 GMT 2023 , Edited by admin on Fri Dec 15 19:46:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID60893995
Created by admin on Fri Dec 15 19:46:29 GMT 2023 , Edited by admin on Fri Dec 15 19:46:29 GMT 2023
PRIMARY
FDA UNII
45P12JNE0L
Created by admin on Fri Dec 15 19:46:29 GMT 2023 , Edited by admin on Fri Dec 15 19:46:29 GMT 2023
PRIMARY