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

MedKoo CAT#: 540219

CAS#: 36531-78-9

Description: Ikarugamycin is a protein translation inhibitor. It also inhibits CCP-dependent phagocytosis and inhibits uptake of oxidized LDL in macrophages.

Chemical Structure

CAS# 36531-78-9

Theoretical Analysis

MedKoo Cat#: 540219
Name: Ikarugamycin
CAS#: 36531-78-9
Chemical Formula: C29H38N2O4
Exact Mass: 478.2832
Molecular Weight: 478.63
Elemental Analysis: C, 72.77; H, 8.00; N, 5.85; O, 13.37

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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IUPAC/Chemical Name: N/A


InChi Code: InChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,34H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4+,12-9+/t16-,17+,18-,19+,20-,21+,22-,23+,24+/m0/s1

SMILES Code: CC[C@H]1[C@@H](C)C[C@H]2[C@H]1C=C[C@H]3[C@H]2C[C@@H](/C=C/4)[C@H]3C/C=C/C(NCCC[C@@H](NC5=O)C(O)=C5C4=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

Preparing Stock Solutions

The following data is based on the product molecular weight 478.63 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

Molarity Calculator

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Dilution Calculator

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2: Lacret R, Oves-Costales D, Gómez C, Díaz C, de la Cruz M, Pérez-Victoria I, Vicente F, Genilloud O, Reyes F. New ikarugamycin derivatives with antifungal and antibacterial properties from Streptomyces zhaozhouensis. Mar Drugs. 2014 Dec 29;13(1):128-40. doi: 10.3390/md13010128. PubMed PMID: 25551780; PubMed Central PMCID: PMC4306928.

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4: Zhang G, Zhang W, Zhang Q, Shi T, Ma L, Zhu Y, Li S, Zhang H, Zhao YL, Shi R, Zhang C. Mechanistic insights into polycycle formation by reductive cyclization in ikarugamycin biosynthesis. Angew Chem Int Ed Engl. 2014 May 5;53(19):4840-4. doi: 10.1002/anie.201402078. Epub 2014 Apr 6. PubMed PMID: 24706593.

5: Greunke C, Antosch J, Gulder TA. Promiscuous hydroxylases for the functionalization of polycyclic tetramate macrolactams--conversion of ikarugamycin to butremycin. Chem Commun (Camb). 2015 Mar 28;51(25):5334-6. doi: 10.1039/c5cc00843c. PubMed PMID: 25711294.

6: Liu C, Wang X, Zhao J, Liu Q, Wang L, Guan X, He H, Xiang W. Streptomyces harbinensis sp. nov., an endophytic, ikarugamycin-producing actinomycete isolated from soybean root [Glycine max (L.) Merr]. Int J Syst Evol Microbiol. 2013 Oct;63(Pt 10):3579-84. doi: 10.1099/ijs.0.050088-0. Epub 2013 Apr 12. PubMed PMID: 23584286.

7: Kyeremeh K, Acquah KS, Sazak A, Houssen W, Tabudravu J, Deng H, Jaspars M. Butremycin, the 3-hydroxyl derivative of ikarugamycin and a protonated aromatic tautomer of 5'-methylthioinosine from a Ghanaian Micromonospora sp. K310. Mar Drugs. 2014 Feb 14;12(2):999-1012. doi: 10.3390/md12020999. PubMed PMID: 24534843; PubMed Central PMCID: PMC3944527.

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16: Greunke C, Glöckle A, Antosch J, Gulder TA. Biocatalytic Total Synthesis of Ikarugamycin. Angew Chem Int Ed Engl. 2017 Apr 3;56(15):4351-4355. doi: 10.1002/anie.201611063. Epub 2017 Jan 27. PubMed PMID: 28128495.

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