MedKoo Cat#: 463456 | Name: Amicoumacin B

Description:

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

Amicoumacin B is an amicoumacin that has been found in N. jinanensis and has quorum-sensing inhibitory activity. It is active against C. violaceum and reduces the expression of the C. violaceum operons vioA, vioB, vioD, and vioE, but increases the expression of vioC, indicating quorum sensing inhibitory activity. Amicoumacin B increases the expression of bone morphogenetic protein 2 (BMP2) in MG-63 cells.

Chemical Structure

Amicoumacin B
Amicoumacin B
CAS#82768-33-0

Theoretical Analysis

MedKoo Cat#: 463456

Name: Amicoumacin B

CAS#: 82768-33-0

Chemical Formula: C20H28N2O8

Exact Mass: 424.1846

Molecular Weight: 424.45

Elemental Analysis: C, 56.60; H, 6.65; N, 6.60; O, 30.15

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Synonym
Amicoumacin B; Amicoumacin-B;
IUPAC/Chemical Name
3-amino-4,5-dihydroxy-6-((1-(8-hydroxy-1-oxoisochroman-3-yl)-3-methylbutyl)amino)-6-oxohexanoic acid
InChi Key
LOXFXXGTOVWWQV-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H28N2O8/c1-9(2)6-12(22-19(28)18(27)17(26)11(21)8-15(24)25)14-7-10-4-3-5-13(23)16(10)20(29)30-14/h3-5,9,11-12,14,17-18,23,26-27H,6-8,21H2,1-2H3,(H,22,28)(H,24,25)
SMILES Code
O=C(O)CC(N)C(O)C(O)C(NC(CC(C)C)C1OC(C2=C(C=CC=C2O)C1)=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
>3 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 424.45 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: Shi WP, Zeng H, Wan CX, Zhou ZB. Amicoumacins from a desert bacterium: quorum sensing inhibitor against Chromobacterium violaceum. Nat Prod Res. 2020 Jul 8:1-5. doi: 10.1080/14786419.2020.1788554. Epub ahead of print. PMID: 32640925. 2: Sun W, Zhang YQ, Huang Y, Zhang YQ, Yang ZY, Liu ZH. Nocardia jinanensis sp. nov., an amicoumacin B-producing actinomycete. Int J Syst Evol Microbiol. 2009 Feb;59(Pt 2):417-20. doi: 10.1099/ijs.0.002899-0. PMID: 19196788. 3: Shinkaruk S, Bennetau B, Babin P, Schmitter JM, Lamothe V, Bennetau-Pelissero C, Urdaci MC. Original preparation of conjugates for antibody production against Amicoumacin-related anti-microbial agents. Bioorg Med Chem. 2008 Oct 15;16(20):9383-91. doi: 10.1016/j.bmc.2008.08.017. Epub 2008 Aug 7. PMID: 18818086.