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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 of CYCLOPENOL

SMILES

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

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
Molecular Formula C17H14N2O4
Molecular Weight 310.3041
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 20.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[On the synthesis of quinoline alkaloids in plants. 2. Fermentativ conversion of the penicillin alkaloids cyclopenin and cyclopenol to viridicatin and viridicatol].
1967-07
STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS. 114. VIRIDICATOL AND CYCLOPENOL, METABOLITES OF PENICILLIUM VIRIDICATUM WESTLING AND PENICILLIUM CYCLOPIUM WESTLING.
1963-11
Patents

Patents

WO2000037665
1

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:53:11 GMT 2025
Edited
by admin
on Mon Mar 31 22:53:11 GMT 2025
Record UNII
4Q2498L80A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOPENOL
Common Name English
NSC-604990
Preferred 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
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
Created by admin on Mon Mar 31 22:53:11 GMT 2025 , Edited by admin on Mon Mar 31 22:53:11 GMT 2025
PRIMARY
PUBCHEM
16681741
Created by admin on Mon Mar 31 22:53:11 GMT 2025 , Edited by admin on Mon Mar 31 22:53:11 GMT 2025
PRIMARY
FDA UNII
4Q2498L80A
Created by admin on Mon Mar 31 22:53:11 GMT 2025 , Edited by admin on Mon Mar 31 22:53:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID60941985
Created by admin on Mon Mar 31 22:53:11 GMT 2025 , Edited by admin on Mon Mar 31 22:53:11 GMT 2025
PRIMARY
CAS
20007-85-6
Created by admin on Mon Mar 31 22:53:11 GMT 2025 , Edited by admin on Mon Mar 31 22:53:11 GMT 2025
PRIMARY
NIH
NCATS
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