CYCLOPENOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H14N2O4
Molecular Weight	310.3041
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)C2=CC=CC=C2NC(=O)[C@]13O[C@@H]3C4=CC(O)=CC=C4

InChI

InChIKey=BDDNYDPRCCDQQJ-PBHICJAKSA-N

InChI=1S/C17H14N2O4/c1-19-15(21)12-7-2-3-8-13(12)18-16(22)17(19)14(23-17)10-5-4-6-11(20)9-10/h2-9,14,20H,1H3,(H,18,22)/t14-,17+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11916664
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23770564 | https://www.ncbi.nlm.nih.gov/pubmed/24773150 | https://www.ncbi.nlm.nih.gov/pubmed/5823102

Cyclopenol is naturally occurring 7-membered 2,5-dioxopiperazine alkaloid isolated from the extract of fungus Penicillium cyclopium , Penicillium sclerotiorum etc. Cyclopenol can be converted into the quinolone viridicatol, by the enzyme cyclopenase present in the conidia. Cyclopenol have phytotoxic and antimicrobial activities.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23770564	Inhibitor 8297		20.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Cyclopenin induced intoxication, prostration and ataxia in day-old chicks at 500 mg/kg, but they recovered within 18 hours. Cyclopenol was inactive against chicks when dosed at levels up to 500 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

CYCLOPENOL

Common Name

English

(2'S,3'R)-3'-(3-HYDROXYPHENYL)-4-METHYLSPIRO(3H-1,4-BENZODIAZEPINE-3,2'-OXIRANE)-2,5(1H,4H)-DIONE

Systematic Name

English

(-)-CYCLOPENOL

Common Name

English

SPIRO(3H-1,4-BENZODIAZEPINE-3,2'-OXIRANE)-2,5(1H,4H)-DIONE, 3'-(3-HYDROXYPHENYL)-4-METHYL-, CIS-(-)-

Systematic Name

English

NSC-604990

Code

English

SPIRO(3H-1,4-BENZODIAZEPINE-3,2'-OXIRANE)-2,5(1H,4H)-DIONE, 3'-(3-HYDROXYPHENYL)-4-METHYL-, (2'S,3'R)-

Systematic Name

English

CYCLOPENOL, (-)-

Common Name

English

Code System Code Type Description

NSC

604990