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Details

Stereochemistry ACHIRAL
Molecular Formula C23H24O5
Molecular Weight 380.4337
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of FOLIPASTATIN

SMILES

C\C=C(\C)C1=CC(O)=C(C)C2=C1OC3=C(C)C(O)=CC(\C(C)=C/C)=C3C(=O)O2

InChI

InChIKey=JJMKBGPTPXPMBH-OXAWKVHCSA-N
InChI=1S/C23H24O5/c1-7-11(3)15-9-17(24)13(5)20-19(15)23(26)28-21-14(6)18(25)10-16(12(4)8-2)22(21)27-20/h7-10,24-25H,1-6H3/b11-7-,12-8-

HIDE SMILES / InChI
Molecular Formula C23H24O5
Molecular Weight 380.4337
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description

Folipastatin is a depsone metabolite first isolated from Aspergillus unguis by researchers at Sankyo, Japan in 1992 as an inhibitor of phospholipase A2. Folipastatin also possesses moderate antibiotic activity as against Gram positive bacteria. It is a component of a mixture of unguinol-related metabolites produced by A. unguis and A. nidulins patented as growth promotants in livestock. More recently, folipastatin was reported as an inhibitor of sterol O-acyltransferase (SOAT) 1 and 2 iso-enzymes in cell-based and enzyme assays.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Phospholipase A2
9
Target ID: Q7M334
Gene ID: NA
Gene Symbol: PLA2G1B
Target Organism: Oryctolagus cuniculus (Rabbit)
Inhibitor
8297
 39.0 µM [IC50]
Inhibitor
8297
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Folipastatin, a new depsidone compound from Aspergillus unguis as an inhibitor of phospholipase A2. Taxonomy, fermentation, isolation, structure determination and biological properties.
1992 Aug
Patents

Patents

EP1745781A1
1
US5350763
1
WO2013024049A1
5

Sample Use Guides

In Vivo Use Guide
Rats: When administered topically, folipastatin showed anti-inflammatory activity to the 12-O-tetradecanoylphorbol 13-acetate-induced ear edema at 0.5mg per rat or mouse.
Route of Administration: Topical
In Vitro Use Guide
Folipastatin inhibited the PLA2 purified from rabbit peritoneal exudate with an IC50 of 39 uM and it suppressed the release of arachidonic acid from rat polymorphonuclear leukocytes (IC50=24 uM).
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:57:15 GMT 2023
Edited
by admin
on Sat Dec 16 01:57:15 GMT 2023
Record UNII
E323392EAO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOLIPASTATIN
Common Name English
11H-DIBENZO(B,E)(1,4)DIOXEPIN-11-ONE, 3,8-DIHYDROXY-4,9-DIMETHYL-1,6-BIS((1Z)-1-METHYL-1-PROPEN-1-YL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
6439424
Created by admin on Sat Dec 16 01:57:15 GMT 2023 , Edited by admin on Sat Dec 16 01:57:15 GMT 2023
PRIMARY
FDA UNII
E323392EAO
Created by admin on Sat Dec 16 01:57:15 GMT 2023 , Edited by admin on Sat Dec 16 01:57:15 GMT 2023
PRIMARY
CAS
139959-71-0
Created by admin on Sat Dec 16 01:57:15 GMT 2023 , Edited by admin on Sat Dec 16 01:57:15 GMT 2023
PRIMARY
NIH
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