MedKoo Cat#: 329872 | Name: Cyclopenin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cyclopenin, also known as NSC 114538 and NSC 604989, is an inhibitor of acetylcholinesterase (AChE; IC50 = 2.04 μM for human recombinant AChE).

Chemical Structure

Cyclopenin
Cyclopenin
CAS#20007-87-8

Theoretical Analysis

MedKoo Cat#: 329872

Name: Cyclopenin

CAS#: 20007-87-8

Chemical Formula: C17H14N2O3

Exact Mass: 294.1004

Molecular Weight: 294.31

Elemental Analysis: C, 69.38; H, 4.79; N, 9.52; O, 16.31

Price and Availability

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5mg USD 550.00 2 Weeks
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Synonym
NSC 604989; NSC-604989; NSC604989; NSC 114538; NSC-114538; NSC114538; Cyclopenin; Cyclopenine; (-)-Cyclopenine; (-)-Cyclopenin
IUPAC/Chemical Name
(3S,3'R)-4-methyl-3'-phenylspiro[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5(1H,4H)-dione
InChi Key
APLKWZASYUZSBL-PBHICJAKSA-N
InChi Code
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)/t14-,17+/m1/s1
SMILES Code
O=C(C1=CC=CC=C1N2)N(C)[C@]3([C@@](O3)([H])C4=CC=CC=C4)C2=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 294.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Mohamed ZS, Todorova-Draganova RW, Luckner M. Nuclear inheritance of the biosynthesis of cyclopenin and cyclopenol in Penicillium cyclopium. Z Allg Mikrobiol. 1984;24(9):615-8. PubMed PMID: 6151759. 2: Richter H, Winter K, el-Kousy S, Luckner M. [The synthesis of derivatives of (plus or minus)-cyclopenin]. Pharmazie. 1974 Aug;29(8):506-10. German. PubMed PMID: 4411221. 3: Nover L, Luckner M. On the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids from Penicillium cyclopium Westling. Eur J Biochem. 1969 Sep;10(2):268-73. PubMed PMID: 5823102. 4: Luckner M. [On the synthesis of quinoline alkaloids in plants. 2. Fermentativ conversion of the penicillin alkaloids cyclopenin and cyclopenol to viridicatin and viridicatol]. Eur J Biochem. 1967 Jul;2(1):74-8. German. PubMed PMID: 6079765. 5: Rhee RP, White JD. Synthesis of cyclopenin and glycosminine from phenylpyruvic acid. J Org Chem. 1977 Nov 11;42(23):3650-3. PubMed PMID: 915586. 6: Kirby GW, Narayanaswami S. Stereochemical studies on the biosynthesis of the alpha beta-didehydro-amino-acid units of mycelianamide, cyclopenin, and cyclopenol. J Chem Soc Perkin 1. 1976;(14):1564-7. PubMed PMID: 987053. 7: White JD, Haefliger WE, Dimsdale MJ. Stereospecific synthesis of dl-cyclopenin and dl-cyclopenol. Tetrahedron. 1970 Jan;26(1):233-42. PubMed PMID: 5415399. 8: Bu YY, Yamazaki H, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M. Penicyrones A and B, an epimeric pair of α-pyrone-type polyketides produced by the marine-derived Penicillium sp. J Antibiot (Tokyo). 2016 Jan;69(1):57-61. doi: 10.1038/ja.2015.82. Epub 2015 Aug 5. PubMed PMID: 26243556. 9: Kusano M, Koshino H, Uzawa J, Fujioka S, Kawano T, Kimura Y. Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum. Biosci Biotechnol Biochem. 2000 Dec;64(12):2559-68. PubMed PMID: 11210117. 10: Mohamed LW, El-Yamany MF. Design and synthesis of novel 1,4-benzodiazepine derivatives and their biological evaluation as cholinesterase inhibitors. Arch Pharm Res. 2012 Aug;35(8):1369-77. doi: 10.1007/s12272-012-0806-3. Epub 2012 Sep 1. PubMed PMID: 22941479. 11: Santini A, Mikušová P, Sulyok M, Krska R, Labuda R, Srobárová A. Penicillium strains isolated from Slovak grape berries taxonomy assessment by secondary metabolite profile. Mycotoxin Res. 2014 Nov;30(4):213-20. doi: 10.1007/s12550-014-0205-3. Epub 2014 Aug 12. PubMed PMID: 25109845. 12: Frisvad JC, Samson RA, Rassing BR, van der Horst MI, van Rijn FT, Stark J. Penicillium discolor, a new species from cheese, nuts and vegetables. Antonie Van Leeuwenhoek. 1997 Aug;72(2):119-26. PubMed PMID: 9298190. 13: Kozlovskiĭ AG, Vinokurova NG, Zhelifonova VP. [Mycotoxins from the fungi Penicillium vulpinum (Cooke & Massee) Seifert & Samson]. Mikrobiologiia. 2000 Jan-Feb;69(1):45-8. Russian. PubMed PMID: 10808488. 14: BRACKEN A, POCKER A, RAISTRICK H. Studies in the biochemistry of microorganisms. 93. Cyclopenin, a nitrogen-containing metabolic product of Penicillium cyclopium Westling. Biochem J. 1954 Aug;57(4):587-95. PubMed PMID: 13198807; PubMed Central PMCID: PMC1269808. 15: Hodge RP, Harris CM, Harris TM. Verrucofortine, a major metabolite of Penicillium verrucosum var. cyclopium, the fungus that produces the mycotoxin verrucosidin. J Nat Prod. 1988 Jan-Feb;51(1):66-73. PubMed PMID: 3373229. 16: Lerbs W, Luckner M. Cyclopeptine synthetase activity in surface cultures of Penicillium cyclopium. J Basic Microbiol. 1985;25(6):387-91. PubMed PMID: 2995633. 17: Jensen B, Knudsen IM, Andersen B, Nielsen KF, Thrane U, Jensen DF, Larsen J. Characterization of microbial communities and fungal metabolites on field grown strawberries from organic and conventional production. Int J Food Microbiol. 2013 Jan 1;160(3):313-22. doi: 10.1016/j.ijfoodmicro.2012.11.005. Epub 2012 Nov 13. PubMed PMID: 23290240. 18: Helbig F, Steighardt J, Roos W. Uric acid is a genuine metabolite of Penicillium cyclopium and stimulates the expression of alkaloid biosynthesis in this fungus. Appl Environ Microbiol. 2002 Apr;68(4):1524-33. PubMed PMID: 11916664; PubMed Central PMCID: PMC123850. 19: Nover L, Luckner M. Mixed functional oxygenations during the biosynthesis of cyclopenin and cyclopenol, benzodiazepine alkaloids of penicillium cyclopium westling. Incorporation of molecular oxygen and NIH-shift. FEBS Lett. 1969 Jun;3(4):292-296. PubMed PMID: 11947032. 20: Kuno F, Otoguro K, Shiomi K, Iwai Y, Omura S. Arisugacins A and B, novel and selective acetylcholinesterase inhibitors from Penicillium sp. FO-4259. I. Screening, taxonomy, fermentation, isolation and biological activity. J Antibiot (Tokyo). 1996 Aug;49(8):742-7. PubMed PMID: 8823504.