Factumycin
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| Category | Antibiotics |
| Catalog number | BBF-03482 |
| CAS | 84600-89-5 |
| Molecular Weight | 778.97 |
| Molecular Formula | C44H62N2O10 |
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Description
It is a polyene antibiotic produced by the strain of Streptomyces lavendulae MA-4758. It has the activity of anti-gram-positive bacteria and gram-negative bacteria, and is an animal growth promoter.
Specification
| Synonyms | Antibiotic A 40A; Mocimycin, 14,17-deepoxy-14,15-didehydro-15,30-dideoxy-17-hydroxy-1-methyl-, (14Z)-; 2H-Pyran-2-acetamide, N-[(2E,4E,6S,7S,9S,10E,12E,14E,16E)-18-(1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-pyridinyl)-8,9-dihydroxy-6-methoxy-5,7,17-trimethyl-18-oxo-2,4,10,12,14,16-octadecahexaen-1-yl]-a-ethyltetrahydro-2,4-dihydroxy-5,5-dimethyl-6-(1E,3Z)-1,3-pentadien-1-yl-, (aS,2S,4S,6S)- |
| IUPAC Name | 2-[(2S,4S,6S)-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]oxan-2-yl]-N-[(2E,4Z,6R,7S,9S,10Z,12E,14E,16E)-8,9-dihydroxy-18-(4-hydroxy-1-methyl-2-oxopyridin-3-yl)-6-methoxy-5,7,17-trimethyl-18-oxooctadeca-2,4,10,12,14,16-hexaenyl]butanamide |
| Canonical SMILES | CCC(C(=O)NCC=CC=C(C)C(C(C)C(C(C=CC=CC=CC=C(C)C(=O)C1=C(C=CN(C1=O)C)O)O)O)OC)C2(CC(C(C(O2)C=CC=CC)(C)C)O)O |
| InChI | InChI=1S/C44H62N2O10/c1-10-12-16-24-36-43(6,7)35(49)28-44(54,56-36)32(11-2)41(52)45-26-20-19-22-30(4)40(55-9)31(5)39(51)34(48)23-18-15-13-14-17-21-29(3)38(50)37-33(47)25-27-46(8)42(37)53/h10,12-25,27,31-32,34-36,39-40,47-49,51,54H,11,26,28H2,1-9H3,(H,45,52)/b12-10-,15-13+,17-14+,20-19+,23-18-,24-16+,29-21+,30-22-/t31-,32?,34-,35-,36-,39?,40-,44-/m0/s1 |
| InChI Key | HMBDLBWGDMNPDW-SUXULKRESA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 988.5°C at 760 mmHg |
| Density | 1.187 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Streptomyces globosus DK15 and Streptomyces ederensis ST13 as new producers of factumycin and tetrangomycin antibiotics
Ivana Charousová, Juraj Medo, Lukáš Hleba, Soňa Javoreková Braz J Microbiol. 2018 Oct-Dec;49(4):816-822. doi: 10.1016/j.bjm.2017.12.007. Epub 2018 Mar 1.
Fifty seven soil-borne actinomycete strains were assessed for the antibiotic production. Two of the most active isolates, designed as Streptomyces ST-13 and DK-15 exhibited a broad range of antimicrobial activity and therefore they were selected for HPLC fractionation against the most suppressed bacteria Staphylococcus aureus (ST-13) and Chromobacterium violaceum (DK-15). LC/MS analysis of extracts showed the presence of polyketides factumycin (DK15) and tetrangomycin (ST13). The taxonomic position of the antibiotic-producing actinomycetes was determined using a polyphasic approach. Phenotypic characterization and 16S rRNA gene sequence analysis of the isolates matched those described for members of the genus Streptomyces. DK-15 strain exhibited the highest 16S rRNA gene sequence similarity to Streptomyces globosus DSM-40815 (T) and Streptomyces toxytricini DSM-40178 (T) and ST-13 strain to Streptomyces ederensis DSM-40741 (T) and Streptomyces phaeochromogenes DSM-40073 (T). For the proper identification, MALDI-TOF/MS profile of whole-cell proteins led to the identification of S. globosus DK-15 (accession number: KX527570) and S. ederensis ST13 (accession number: KX527568). To our knowledge, there is no report about the production of these antibiotics by S.globosus and S. ederensis, thus isolates DK15 and ST13 identified as S. globosus DK-15 and S.ederensis ST-13 can be considered as new sources of these unique antibacterial metabolites.
2. UK-69,753, a novel member of the efrotomycin family of antibiotics. I. Taxonomy of the producing organism, fermentation and isolation
M S Pacey, M R Jefson, L H Huang, W P Cullen, H Maeda, J Tone, S Nishiyama, K Kaneda, M Ishiguro J Antibiot (Tokyo). 1989 Oct;42(10):1453-9. doi: 10.7164/antibiotics.42.1453.
UK-69,753 is a novel antibiotic structurally related to efrotomycin and factumycin, produced by a new strain of Amycolatopsis orientalis (ATCC 53550). The antibiotic potency in the fermentation broth was monitored by HPLC with diode array detection. A six tube counter current distribution was used to purify UK-69,753.
3. Discovery of a new family of Dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis
Chun Gui, Qinglian Li, Xuhua Mo, Xiangjing Qin, Junying Ma, Jianhua Ju Org Lett. 2015 Feb 6;17(3):628-31. doi: 10.1021/ol5036497. Epub 2015 Jan 26.
Bioinformatic analyses indicate that TrdC, SlgL, LipX2, KirHI, and FacHI belong to a group of highly homologous proteins involved in biosynthesis of actinomycete-derived tirandamycin B, streptolydigin, α-lipomycin, kirromycin, and factumycin, respectively. However, assignment of their biosynthetic roles has remained elusive. Gene inactivation and complementation, in vitro biochemical assays with synthetic analogues, point mutations, and phylogenetic tree analyses reveal that these proteins represent a new family of Dieckmann cyclases that drive tetramic acid and pyridone scaffold biosynthesis.
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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 ╳
