R176502
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| Category | Bioactive by-products |
| Catalog number | BBF-03361 |
| CAS | |
| Molecular Weight | 854 |
| Molecular Formula | C47H67NO13 |
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Description
R176502 is a bafilolide metabolite with potent antiproliferative activity, which is produced by Micromonospora sp. JS1035. It inhibits proliferation of MCF-7, HT-29, K562/C1000 and Malme-3M cells with IC50 values of 1.29 ± 0.35, 0.61 ± 0.04, 9.29 ± 7.35, 7.96 ± 2.75 nmol/L.
Specification
| Synonyms | R 176502 |
| IUPAC Name | [(2R,4R,5S,6R)-6-[(1E,3E)-hexa-1,3-dienyl]-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,4E,6E,9S,10S,11R,12E,14Z)-10-hydroxy-3,15-dimethoxy-7,9,11,13-tetramethyl-16-oxo-1-oxacyclohexadeca-4,6,12,14-tetraen-2-yl]pentan-2-yl]-5-methyloxan-4-yl] (E)-4-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-4-oxobut-2-enoate |
| Canonical SMILES | CCC=CC=CC1C(C(CC(O1)(C(C)C(C(C)C2C(C=CC=C(CC(C(C(C=C(C=C(C(=O)O2)OC)C)C)O)C)C)OC)O)O)OC(=O)C=CC(=O)NC3=C(CCC3=O)O)C |
| InChI | InChI=1S/C47H67NO13/c1-11-12-13-14-17-36-31(6)39(59-41(52)22-21-40(51)48-42-34(49)19-20-35(42)50)26-47(56,61-36)33(8)44(54)32(7)45-37(57-9)18-15-16-27(2)23-29(4)43(53)30(5)24-28(3)25-38(58-10)46(55)60-45/h12-18,21-22,24-25,29-33,36-37,39,43-45,49,53-54,56H,11,19-20,23,26H2,1-10H3,(H,48,51)/b13-12+,17-14+,18-15+,22-21+,27-16+,28-24+,38-25-/t29-,30+,31+,32-,33-,36+,37-,39+,43-,44+,45+,47+/m0/s1 |
| InChI Key | JXMDVHROXKUEAM-ZBMDCPOGSA-N |
Properties
| Appearance | Pale Brown Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 114-120°C |
Reference Reading
1. R176502, a new bafilolide metabolite with potent antiproliferative activity from a novel Micromonospora species
Jodi A Laakso, Ursula M Mocek, Jacky Van Dun, Walter Wouters, Michel Janicot J Antibiot (Tokyo). 2003 Nov;56(11):909-16. doi: 10.7164/antibiotics.56.909.
During the course of a screening program intended to identify new antiproliferative agents, a new bafilolide metabolite was discovered. R176502 (1) was isolated from the liquid fermentation cultures of a novel Micromonospora species found in African river bottom sediment. It was purified from ethyl acetate extracts using a series of countercurrent chromatographic steps. The structure was determined using 1- and 2-D NMR experiments. Three previously described bafilomycins (bafilomycins A1 (2), B1 (3), and B2 (4)) were also isolated (from other microbial strains). R176502 exhibited potency for inhibition of tumor cell proliferation in the nM range of concentrations.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
