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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23N3O2
Molecular Weight 325.4048
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PREECHINULIN

SMILES

C[C@@H]1NC(=O)[C@H](CC2=C(NC3=C2C=CC=C3)C(C)(C)C=C)NC1=O

InChI

InChIKey=LVPZJIGICMPWFH-NHYWBVRUSA-N
InChI=1S/C19H23N3O2/c1-5-19(3,4)16-13(12-8-6-7-9-14(12)21-16)10-15-18(24)20-11(2)17(23)22-15/h5-9,11,15,21H,1,10H2,2-4H3,(H,20,24)(H,22,23)/t11-,15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H23N3O2
Molecular Weight 325.4048
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Aspergillus fungi are important producers of metabolites with toxic potential; they can produce a wide variety of secondary metabolites one of which is preechinulin. It was shown, that this compound failed to protect cells against NO toxicity or induce these alterations, suggesting their link with the cytoprotective mechanism.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Taxonomic Characterization and Secondary Metabolite Profiling of Aspergillus Section Aspergillus Contaminating Feeds and Feedstuffs.
2015-09-02
Neoechinulin a imparts resistance to acute nitrosative stress in PC12 cells: a potential link of an elevated cellular reserve capacity for pyridine nucleotide redox turnover with cytoprotection.
2012
Isolation of talathermophilins from the thermophilic fungus Talaromyces thermophilus YM3-4.
2011-10-28

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Cells in 6-well plates were incubated with preechinulin (each 100 µmol/L) or their vehicle (0.1% DMSO) for the indicated times, and GSH content in the cells was measured. Preechinulin failed to protect cells against NO toxicity or induce these alterations, suggesting their link with the cytoprotective mechanism.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:09:23 GMT 2025
Edited
by admin
on Mon Mar 31 23:09:23 GMT 2025
Record UNII
NFA24NXF2J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PREECHINULIN
Common Name English
2,5-PIPERAZINEDIONE, 3-((2-(1,1-DIMETHYL-2-PROPEN-1-YL)-1H-INDOL-3-YL)METHYL)-6-METHYL-, (3S,6S)-
Preferred Name English
2,5-PIPERAZINEDIONE, 3-((2-(1,1-DIMETHYL-2-PROPENYL)-1H-INDOL-3-YL)METHYL)-6-METHYL-, (3S-CIS)-
Systematic Name English
Code System Code Type Description
CAS
21008-43-5
Created by admin on Mon Mar 31 23:09:23 GMT 2025 , Edited by admin on Mon Mar 31 23:09:23 GMT 2025
PRIMARY
FDA UNII
NFA24NXF2J
Created by admin on Mon Mar 31 23:09:23 GMT 2025 , Edited by admin on Mon Mar 31 23:09:23 GMT 2025
PRIMARY
PUBCHEM
44445554
Created by admin on Mon Mar 31 23:09:23 GMT 2025 , Edited by admin on Mon Mar 31 23:09:23 GMT 2025
PRIMARY