MedKoo Cat#: 584463 | Name: Cycloechinulin
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Description:

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

Cycloechinulin is a diketopiperazine fungal metabolite originally isolated from A. ochraceus. It reduces weight gain of corn earworms by 33% compared to controls when used at a dose of 100 ppm in the diet.

Chemical Structure

Cycloechinulin
Cycloechinulin
CAS#143086-29-7

Theoretical Analysis

MedKoo Cat#: 584463

Name: Cycloechinulin

CAS#: 143086-29-7

Chemical Formula: C20H21N3O3

Exact Mass: 351.1583

Molecular Weight: 351.41

Elemental Analysis: C, 68.36; H, 6.02; N, 11.96; O, 13.66

Price and Availability

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1mg USD 450.00 Back order
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Related CAS #
No Data
Synonym
Cycloechinulin
IUPAC/Chemical Name
(3S)-2,3,8,9-tetrahydro-11-methoxy-3,8,8-trimethyl-pyrazino[1',2':1,2]azocino[5,4-b]indole-1,4-dione
InChi Key
RCTQPWJZZZLMBI-RPHUSYQJSA-N
InChi Code
InChI=1S/C20H21N3O3/c1-11-19(25)23-8-7-20(2,3)17-14(10-16(23)18(24)21-11)13-6-5-12(26-4)9-15(13)22-17/h5-11,22H,1-4H3,(H,21,24)/b8-7-,16-10-/t11-/m0/s1
SMILES Code
O=C1N[C@@H](C)C(N2/C1=C\C3=C(C(C)(C)/C=C\2)NC4=C3C=CC(OC)=C4)=O
Appearance
Solid powder
Purity
>95% (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 351.41 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: Ishikawa K, Hosoe T, Itabashi T, Wakana D, Takizawa K, Yaguchi T, Kawai K. Novoamauromine and ent-Cycloechinulin: two new diketopiperazine derivatives from Aspergillus novofumigatus. Chem Pharm Bull (Tokyo). 2010 May;58(5):717-9. doi: 10.1248/cpb.58.717. PMID: 20460802. 2: Kjærbølling I, Vesth TC, Frisvad JC, Nybo JL, Theobald S, Kuo A, Bowyer P, Matsuda Y, Mondo S, Lyhne EK, Kogle ME, Clum A, Lipzen A, Salamov A, Ngan CY, Daum C, Chiniquy J, Barry K, LaButti K, Haridas S, Simmons BA, Magnuson JK, Mortensen UH, Larsen TO, Grigoriev IV, Baker SE, Andersen MR. Linking secondary metabolites to gene clusters through genome sequencing of six diverse Aspergillus species. Proc Natl Acad Sci U S A. 2018 Jan 23;115(4):E753-E761. doi: 10.1073/pnas.1715954115. Epub 2018 Jan 9. PMID: 29317534; PMCID: PMC5789934. 3: Dao DQ, Phan TTT, Nguyen TLA, Trinh PTH, Tran TTV, Lee JS, Shin HJ, Choi BK. Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus. J Chem Inf Model. 2020 Mar 23;60(3):1329-1351. doi: 10.1021/acs.jcim.9b00964. Epub 2020 Feb 12. PMID: 31999921. 4: Shin HJ, Choi BK, Trinh PTH, Lee HS, Kang JS, Van TTT, Lee HS, Lee JS, Lee YJ, Lee J. Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp. Mar Drugs. 2018 Jan 5;16(1):14. doi: 10.3390/md16010014. PMID: 29304006; PMCID: PMC5793062. 5: Hong SB, Go SJ, Shin HD, Frisvad JC, Samson RA. Polyphasic taxonomy of Aspergillus fumigatus and related species. Mycologia. 2005 Nov- Dec;97(6):1316-29. doi: 10.3852/mycologia.97.6.1316. PMID: 16722222.