MedKoo Cat#: 591164 | Name: Amicoumacin A

Description:

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

Amicoumacin A has antibacterial activity, & strongly suppresses inflammatory & ulcer activity.

Chemical Structure

Amicoumacin A
Amicoumacin A
CAS#78654-44-1 (free base)

Theoretical Analysis

MedKoo Cat#: 591164

Name: Amicoumacin A

CAS#: 78654-44-1 (free base)

Chemical Formula: C20H29N3O7

Exact Mass: 423.2006

Molecular Weight: 423.47

Elemental Analysis: C, 56.73; H, 6.90; N, 9.92; O, 26.45

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
78654-44-1 (free base); 78683-77-9 (hydrochloride)
Synonym
Amicoumacin A;
IUPAC/Chemical Name
Adipamide, 4-amino-2,3-dihydroxy-N-(1-(8-hydroxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl)-3-methylbutyl)-
InChi Key
DCPWYLSPIAHJFU-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H29N3O7/c1-9(2)6-12(23-19(28)18(27)17(26)11(21)8-15(22)25)14-7-10-4-3-5-13(24)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,24,26-27H,6-8,21H2,1-2H3,(H2,22,25)(H,23,28)
SMILES Code
O=C(NC(C1CC2=CC=CC(O)=C2C(O1)=O)CC(C)C)C(O)C(O)C(N)CC(N)=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 423.47 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: Gao XY, Liu Y, Miao LL, Li EW, Hou TT, Liu ZP. Mechanism of anti-Vibrio activity of marine probiotic strain Bacillus pumilus H2, and characterization of the active substance. AMB Express. 2017 Dec;7(1):23. doi: 10.1186/s13568-017-0323-3. Epub 2017 Jan 17. PubMed PMID: 28097594; PubMed Central PMCID: PMC5241254. 2: Prokhorova IV, Akulich KA, Makeeva DS, Osterman IA, Skvortsov DA, Sergiev PV, Dontsova OA, Yusupova G, Yusupov MM, Dmitriev SE. Amicoumacin A induces cancer cell death by targeting the eukaryotic ribosome. Sci Rep. 2016 Jun 14;6:27720. doi: 10.1038/srep27720. PubMed PMID: 27296282; PubMed Central PMCID: PMC4906347. 3: Melnikov SV, Söll D, Steitz TA, Polikanov YS. Insights into RNA binding by the anticancer drug cisplatin from the crystal structure of cisplatin-modified ribosome. Nucleic Acids Res. 2016 Jun 2;44(10):4978-87. doi: 10.1093/nar/gkw246. Epub 2016 Apr 13. PubMed PMID: 27079977; PubMed Central PMCID: PMC4889946. 4: Jiang J, Seo H, Chow CS. Post-transcriptional Modifications Modulate rRNA Structure and Ligand Interactions. Acc Chem Res. 2016 May 17;49(5):893-901. doi: 10.1021/acs.accounts.6b00014. Epub 2016 Apr 11. PubMed PMID: 27064497. 5: Li Y, Li Z, Yamanaka K, Xu Y, Zhang W, Vlamakis H, Kolter R, Moore BS, Qian PY. Directed natural product biosynthesis gene cluster capture and expression in the model bacterium Bacillus subtilis. Sci Rep. 2015 Mar 24;5:9383. doi: 10.1038/srep09383. PubMed PMID: 25807046; PubMed Central PMCID: PMC4894447. 6: Polikanov YS, Osterman IA, Szal T, Tashlitsky VN, Serebryakova MV, Kusochek P, Bulkley D, Malanicheva IA, Efimenko TA, Efremenkova OV, Konevega AL, Shaw KJ, Bogdanov AA, Rodnina MV, Dontsova OA, Mankin AS, Steitz TA, Sergiev PV. Amicoumacin a inhibits translation by stabilizing mRNA interaction with the ribosome. Mol Cell. 2014 Nov 20;56(4):531-40. doi: 10.1016/j.molcel.2014.09.020. Epub 2014 Oct 9. PubMed PMID: 25306919; PubMed Central PMCID: PMC4253140. 7: Lama A, Pané-Farré J, Chon T, Wiersma AM, Sit CS, Vederas JC, Hecker M, Nakano MM. Response of methicillin-resistant Staphylococcus aureus to amicoumacin A. PLoS One. 2012;7(3):e34037. doi: 10.1371/journal.pone.0034037. Epub 2012 Mar 30. PubMed PMID: 22479511; PubMed Central PMCID: PMC3316591. 8: Li Y, Xu Y, Liu L, Han Z, Lai PY, Guo X, Zhang X, Lin W, Qian PY. Five new amicoumacins isolated from a marine-derived bacterium Bacillus subtilis. Mar Drugs. 2012 Feb;10(2):319-28. doi: 10.3390/md10020319. Epub 2012 Feb 3. PubMed PMID: 22412803; PubMed Central PMCID: PMC3296999. 9: Hashimoto M, Taguchi T, Nishida S, Ueno K, Koizumi K, Aburada M, Ichinose K. Isolation of 8'-phosphate ester derivatives of amicoumacins: structure-activity relationship of hydroxy amino acid moiety. J Antibiot (Tokyo). 2007 Dec;60(12):752-6. doi: 10.1038/ja.2007.99. Erratum in: J Antibiot (Tokyo). 2008 Jan;61(1):C-1. PubMed PMID: 18277000. 10: Pinchuk IV, Bressollier P, Verneuil B, Fenet B, Sorokulova IB, Mégraud F, Urdaci MC. In vitro anti-Helicobacter pylori activity of the probiotic strain Bacillus subtilis 3 is due to secretion of antibiotics. Antimicrob Agents Chemother. 2001 Nov;45(11):3156-61. PubMed PMID: 11600371; PubMed Central PMCID: PMC90797. 11: Itoh J, Omoto S, Shomura T, Nishizawa N, Miyado S, Yuda Y, Shibata U, Inouye S. Amicoumacin-A, a new antibiotic with strong antiinflammatory and antiulcer activity. J Antibiot (Tokyo). 1981 May;34(5):611-3. PubMed PMID: 7275843.