MedKoo Cat#: 329898 | Name: Epicoccamide
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Description:

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

Epicoccamide is a marine fungal metabolite originally isolated from E. purpurascens.

Chemical Structure

Epicoccamide
Epicoccamide
CAS#606139-26-8

Theoretical Analysis

MedKoo Cat#: 329898

Name: Epicoccamide

CAS#: 606139-26-8

Chemical Formula: C29H51NO9

Exact Mass: 557.3564

Molecular Weight: 557.73

Elemental Analysis: C, 62.45; H, 9.22; N, 2.51; O, 25.82

Price and Availability

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1mg USD 450.00 Back order
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Related CAS #
No Data
Synonym
Epicoccamide;
IUPAC/Chemical Name
5-hydroxy-1,2-dimethyl-4-(2-methyl-16-(((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexadecanoyl)-1,2-dihydro-3H-pyrrol-3-one
InChi Key
NHTZEZZBJRROIH-XIECNSLGSA-N
InChi Code
InChI=1S/C29H51NO9/c1-19(23(32)22-24(33)20(2)30(3)28(22)37)16-14-12-10-8-6-4-5-7-9-11-13-15-17-38-29-27(36)26(35)25(34)21(18-31)39-29/h19-21,25-27,29,31,34-37H,4-18H2,1-3H3/t19?,20?,21-,25-,26+,27+,29-/m1/s1
SMILES Code
O[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OCCCCCCCCCCCCCCC(C)C(C2=C(O)N(C)C(C)C2=O)=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 557.73 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: Kwon HJ, Choi EH, Choi U, Park SH. Biological production of epicoccamide- aglycone and its cytotoxicity. Bioorg Med Chem Lett. 2023 Oct 13;96:129524. doi: 10.1016/j.bmcl.2023.129524. Epub ahead of print. PMID: 37839713. 2: Wright AD, Osterhage C, König GM. Epicoccamide, a novel secondary metabolite from a jellyfish-derived culture of Epicoccum purpurascens. Org Biomol Chem. 2003 Feb 7;1(3):507-10. doi: 10.1039/b208588g. PMID: 12926253. 3: Loscher S, Schobert R. Total synthesis and absolute configuration of epicoccamide D, a naturally occurring mannosylated 3-acyltetramic acid. Chemistry. 2013 Aug 5;19(32):10619-24. doi: 10.1002/chem.201301914. Epub 2013 Jun 25. PMID: 23801547. 4: Zhang T, Cai G, Rong X, Xu J, Jiang B, Wang H, Li X, Wang L, Zhang R, He W, Yu L. Mining and characterization of the PKS-NRPS hybrid for epicoccamide A: a mannosylated tetramate derivative from Epicoccum sp. CPCC 400996. Microb Cell Fact. 2022 Nov 24;21(1):249. doi: 10.1186/s12934-022-01975-2. PMID: 36419162; PMCID: PMC9685919. 5: Harwoko H, Lee J, Hartmann R, Mándi A, Kurtán T, Müller WEG, Feldbrügge M, Kalscheuer R, Ancheeva E, Daletos G, Frank M, Liu Z, Proksch P. Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079. Fitoterapia. 2020 Oct;146:104698. doi: 10.1016/j.fitote.2020.104698. Epub 2020 Jul 31. PMID: 32745508. 6: Wangun HV, Dahse HM, Hertweck C. Epicoccamides B-D, glycosylated tetramic acid derivatives from an Epicoccum sp. associated with the tree fungus Pholiota squarrosa. J Nat Prod. 2007 Nov;70(11):1800-3. doi: 10.1021/np070245q. Epub 2007 Oct 30. PMID: 17966985.