Naphthomycin C
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| Category | Antibiotics |
| Catalog number | BBF-01987 |
| CAS | 86825-87-8 |
| Molecular Weight | 671.77 |
| Molecular Formula | C39H45NO9 |
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Description
Naphthomycin C is a macrolide (Ansa family) antibiotic produced by strains such as Str.collinus Tv105, Str. galbus subsp. griseosporeus Tv 353, Str. diastatochromogene, Str. sp. Y83 40369.
Specification
| IUPAC Name | (7Z,9S,10S,11S,12Z,14S,16Z,20S,21S,22Z,24Z,26Z)-4,10,14,20-tetrahydroxy-3,7,9,11,17,21-hexamethyl-29-azatricyclo[28.3.1.05,33]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone |
| Canonical SMILES | CC1C=CC=CC=CC(=O)NC2=CC(=O)C3=C(C2=O)C=C(C(=C3C(=O)C(=CC(C(C(C=CC(CC=C(C(=O)CC1O)C)O)C)O)C)C)O)C |
| InChI | InChI=1S/C39H45NO9/c1-21-11-9-7-8-10-12-33(45)40-29-19-32(44)34-28(39(29)49)18-26(6)38(48)35(34)37(47)25(5)17-24(4)36(46)23(3)14-16-27(41)15-13-22(2)31(43)20-30(21)42/h7-14,16-19,21,23-24,27,30,36,41-42,46,48H,15,20H2,1-6H3,(H,40,45)/b8-7-,11-9-,12-10-,16-14-,22-13-,25-17-/t21-,23-,24-,27-,30-,36-/m0/s1 |
| InChI Key | AZDWXKPJAPDNFY-HKORKPFASA-N |
Properties
| Appearance | Grayish Yellow Powder |
| Melting Point | 218°C (dec.) |
Reference Reading
1. Naphthomycins L-N, ansamycin antibiotics from Streptomyces sp. CS
Yin-He Yang, Xiao-Li Fu, Liang-Qun Li, Ying Zeng, Cheng-Yun Li, Yi-Neng He, Pei-Ji Zhao J Nat Prod. 2012 Jul 27;75(7):1409-13. doi: 10.1021/np300109s. Epub 2012 Jun 28.
Previous analyses of the naphthomycin biosynthetic gene cluster and a comparison with known naphthomycin-type products from Streptomyces sp. CS have suggested that new products can be found from this strain. In this study, screening by LC-MS of Streptomyces sp. CS products formed under different culture conditions revealed several unknown peaks in the product spectra of extracts derived from oatmeal medium cultures. Three new naphthomycins, naphthomycins L (1), M (2), and N (3), and the known naphthomycins A (4), E (5), and D (6) were obtained. The structures were elucidated using spectroscopic data from 1D and 2D NMR and HRESIMS experiments.
2. The complete genome sequence of Streptomyces autolyticus CGMCC 0516, the producer of geldanamycin, autolytimycin, reblastatin and elaiophylin
Min Yin, Mingxing Jiang, Zhen Ren, Yilong Dong, Tao Lu J Biotechnol. 2017 Jun 20;252:27-31. doi: 10.1016/j.jbiotec.2017.04.037. Epub 2017 May 2.
Streptomyces autolyticus CGMCC 0516 produces the anti-tumor benzoquinone ansamycins geldanamycin, autolytimycin, and reblastatin and the 16-membered macrodiolide elaiophylin. Here, we report the complete genome sequence of S. autolyticus CGMCC 0516, which consists of a 10,029,028bp linear chromosome and seven circular plasmids. Fifty-seven putative biosynthetic gene clusters for secondary metabolites were found. The geldanamycin, autolytimycin, and reblastatin biosynthetic gene clusters were located on the left arm (2.06-2.15Mb) of the chromosome, and the elaiophylin gene cluster was located on the right arm (9.45-9.53Mb). Twenty-one putative gene clusters with high or moderate similarity to important antibiotic biosynthetic gene clusters were found, including the antitumor agents echoside, bafilomycin, hygrocin, and toxoflavin; the antibacterial/antifungal agents nigericin, skyllamycin, kanamycin, naphthomycin, eco-02301, and bottromycin A2; the immunosuppressants meridamycin and brasilicardin A; the anti-inflammatory agent cyclooctatin; and the acute iron poisoning medication desferrioxamine B. The genome sequence reported here will enable us to study the biosynthetic mechanism of these important antibiotics and will facilitate the discovery of novel secondary metabolites with potential applications to human health.
3. Biosynthesis of 3,5-AHBA-derived natural products
Qianjin Kang, Yuemao Shen, Linquan Bai Nat Prod Rep. 2012 Feb;29(2):243-63. doi: 10.1039/c2np00019a. Epub 2011 Dec 22.
Covering: 1957 to 2011. 3-Amino-5-hydroxy benzoic acid (3,5-AHBA) is a precursor for a large group of natural products, including the family of naphthalenic and benzenic ansamycins, the unique saliniketals, and the family of mitomycins. This review covers the biosynthesis of AHBA-derived natural products from a molecular genetics, chemical, and biochemical perspectives, and 174 references are cited.
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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 ╳
