CURVULARIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20O5
Molecular Weight	292.327
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1CCCCCC(=O)C2=C(CC(=O)O1)C=C(O)C=C2O

InChI

InChIKey=VDUIGYAPSXCJFC-JTQLQIEISA-N

InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H20O5
Molecular Weight	292.327
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22767531
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12527810

Curvularin (S-curvularin) is a macrocyclic lactone with cytotoxic activity. Curvularin inhibits cell division as well as expression of human inducible nitric oxide synthase (iNOS), an enzyme critically involved in pro-inflammatory immune processes. Also was discovered that S-curvularin is an effective anti-inflammatory compound that may serve as a lead compound for the development of new drugs for the therapy of chronic inflammatory diseases, such as Rheumatoid Arthritis or inflammatory bowel disease. S-curvularin is an inhibitor of iNOS-dependent NO production, acting on the Janus tyrosine kinase-STAT pathway.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Jak-STAT signaling pathway 9 Target ID: map04630 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12527810	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22767531	Palliative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Sporogen, S14-95, and S-curvularin, three inhibitors of human inducible nitric-oxide synthase expression isolated from fungi.	2003 Feb	12527810
Inhibitors of inducible NO synthase expression: total synthesis of (S)-curvularin and its ring homologues.	2008 Jun	18366037

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

To analyze the effect of S-curvularin on human iNOS promoter activity, there was incubated A549/8 cells stably transfected with pNOSII(16)Luc with different concentrations of S-curvularin: 1–100 μg/ml, 3–340 μM. It was shown, S-curvularin inhibited the CM-induced iNOS promoter activity in A549/8-pNOSII(16)Luc cells in a concentration-dependent manner. To study the effect of S-curvularin on STAT1 activation, Western blots using an antibody that detects the tyrosine (Tyr701) phosphorylation of STAT1 (corresponds to STAT1 activation; were performed. Incubation of A549/8 for 5 min with cytokine mixture (CM) resulted in a marked enhancement of STAT1 tyrosine phosphorylation. Coincubation of CM-treated A549/8 cells with -curvularin (100 μM) significantly reduced this STAT1 tyrosine phosphorylation.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:42:26 GMT 2023` Edited by `admin` on `Fri Dec 15 19:42:26 GMT 2023`
Record UNII	WT39K5T3BX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CURVULARIN

Common Name

English

NSC-166071

Code

English

(4S)-4,5,6,7,8,9-HEXAHYDRO-11,13-DIHYDROXY-4-METHYL-2H-3-BENZOXACYCLODODECIN-2,10(1H)-DIONE

Systematic Name

English

CURVULARIN [MI]

Common Name

English

Code System Code Type Description

WIKIPEDIA

Curvularin