(-)-Cyclopenine
Basic information
- CAS
20007-87-8- Standard SMILES
CN1C(=O)c2ccccc2NC(=O)[C@]12O[C@@H]2c1ccccc1- InChIKey
APLKWZASYUZSBL-PBHICJAKSA-N- Molecular formula
- C17H14N2O3
- Average molar mass
- 294.3 g/mol
- Monoisotopic mass
- 294.10044231
Overview
(-)-cyclopenine is an epoxide.
Names & identifiers
- Preferred name
- (-)-Cyclopenine
- IUPAC
- (3S,3'R)-4-methyl-3'-phenylspiro[1H-1,4-benzodiazepine-3,2'-oxirane]-2,5-dione
- English name
- cyclopenin
- Molecular formula
- C17H14N2O3
- Molecular weight
- 294.31
Names & synonyms
(-)-Cyclopenine(-)-CyclopeninNSC 114538NSC 604989(+/-)-CyclopenineNSC114538Cyclopenine (8CI)UNII-BTA4FR48AAMLS000876987MEGxm0_000048orb1700783CHEMBL1700550
Show more names
NSC604989NSC-604989cyclopeninNSC-114538Spiro[3H-1,4-benzodiazepine-3,2'-oxirane]-2,5(1H,4H)-dione, 4-methyl-3'-phenyl-, (2'R,3'S)-rel-(-)-
ACon0_000794ACon1_000957DTXSID00893999CHEBI:193522HMS2268G2319553-26-5Spiro(3H-1,4-benzodiazepine-3,2'-oxirane)-2,5(1H,4H)-dione, 4-methyl-3'-phenyl-, cis-(-)-AKOS040748199
Database identifiers
- CAS
20007-87-8- PubChem CID
- 73525
- DTXSID
DTXSID00893999- ChEMBL
CHEMBL1700550- ChEBI
CHEBI:193522- UNII
- BTA4FR48AA
- Nikkaji
- J462.554D
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 61.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 488
Physicochemical properties
- Melting point
- 183 · 183-184 °C
- Boiling point
- 572.5 · 572.5±50.0 °C(Predicted)
- Density
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMSO: soluble
- form
- A solid
- pka
- 12.92 · 12.92±0.40(Predicted)
- biological source
- plant
- Water Solubility
- water: slightly soluble
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- 1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)
- InChIKey
- APLKWZASYUZSBL-UHFFFAOYSA-N
- SMILES
- N1(C3(OC3c4ccccc4)C(=O)Nc2c(cccc2)C1=O)C
- FDA UNII
- 4 FR48AA · BTA4FR48AA
- UNSPSC Code
- 12352205 · 12352205
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P321-P330-P362+P364-P501
Chemistry & industry
Applications
DescriptionCyclopenin is an inhibitor of acetylcholinesterase (AChE; IC50 = 2.04 μM for human recombinant AChE) that is produced by Penicillium. It exhibits greater than 2,000-fold selectivity over recombinant equine butyrylcholinesterase with an IC50 value greater than 4,080 μM. Cyclopenin also has antibacterial activity against E. coli and M. pyogenes.
Uses(-)-Cyclopenin ((-)-Cyclopenine) is the enantiomer of Cyclopenin. Cyclopenin is a selective acetylcholinesterase (AChE) inhibitor with the IC50 of 2.04 μM[1].
Additional notes
DefinitionChEBI: (-)-cyclopenine is an epoxide.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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