Napyradiomycin A2
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| Category | Antibiotics |
| Catalog number | BBF-01993 |
| CAS | 111216-62-7 |
| Molecular Weight | 497.41 |
| Molecular Formula | C25H30Cl2O6 |
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Description
Napyradiomycin A2 is an antibiotic produced by Chainia rubra MG802-AF1. It has anti-gram-positive bacteria and mycobacterial activity.
Specification
| Synonyms | 16-Hydroxy-17-methylenenapyradiomycin A1 |
| IUPAC Name | (3R,4aR,10aS)-3,4a-dichloro-6,8-dihydroxy-10a-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl]-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione |
| Canonical SMILES | CC(=C)C(CCC(=CCC12C(=O)C3=C(C(=CC(=C3)O)O)C(=O)C1(CC(C(O2)(C)C)Cl)Cl)C)O |
| InChI | InChI=1S/C25H30Cl2O6/c1-13(2)17(29)7-6-14(3)8-9-25-21(31)16-10-15(28)11-18(30)20(16)22(32)24(25,27)12-19(26)23(4,5)33-25/h8,10-11,17,19,28-30H,1,6-7,9,12H2,2-5H3/b14-8+/t17?,19-,24+,25+/m1/s1 |
| InChI Key | MUVCLXZNRJJIGV-IYESRBMVSA-N |
Properties
| Appearance | Yellow Brown Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 682.6±55.0°C at 760 mmHg |
| Melting Point | 62-67°C |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Terpenoids Produced by Actinomycetes: Napyradiomycins from Streptomyces antimycoticus NT17
Keiichiro Motohashi, Masayuki Sue, Kazuo Furihata, Shuichiro Ito, Haruo Seto J Nat Prod. 2008 Apr;71(4):595-601. doi: 10.1021/np070575a. Epub 2008 Feb 14.
Napyradiomycin SR ( 1), 16-dechloro-16-hydroxynapyradiomycin C2 ( 2), 18-hydroxynapyradiomycin A1 ( 3), 18-oxonapyradiomycin A1 ( 4), 16-oxonapyradiomycin A2 ( 5), 7-demethyl SF2415A3 ( 6), 7-demethyl A80915B ( 7), and ( R)-3-chloro-6-hydroxy-8-methoxy-alpha-lapachone ( 8) were isolated from the culture broth of Streptomyces antimycoticus NT17. These compounds are derivatives of the napyradiomycins isolated previously from Chainia rubra or Streptomyces aculeolatus. The structures of the new compounds, some of which exhibit antibacterial activities, were established by comparing their NMR data with data of related known compounds. The unique structure of 1, containing a highly strained ring, was established by NMR and was confirmed by X-ray analysis. Two of the compounds are C-16 stereoisomers of napyradiomycin A2 and are named napyradiomycins A2a ( 9a) and A2b ( 9b).
2. New antibiotic napyradiomycins A2 and B4 and stereochemistry of napyradiomycins
K Shiomi, H Nakamura, H Iinuma, H Naganawa, T Takeuchi, H Umezawa, Y Iitaka J Antibiot (Tokyo). 1987 Sep;40(9):1213-9. doi: 10.7164/antibiotics.40.1213.
Napyradiomycins A2 and B4, new members of the napyradiomycins, have been isolated from the culture broth of Chainia rubra MG802-AF1. The structure of napyradiomycin A2 was elucidated as 16-hydroxy-17-methylenenapyradiomycin A1 by NMR studies. The absolute structure of napyradiomycin B4 was determined as 13-hydroxy-13-methylnapyradiomycin B1 by X-ray crystallography and therefore the configuration of C(4a) in other napyradiomycins is assumed as the R configuration. The geometrical isomerism of napyradiomycin C1 was estimated as 12E and 16E by nuclear Overhauser effect experiments.
3. Biosynthesis of napyradiomycins
K Shiomi, H Iinuma, H Naganawa, K Isshiki, T Takeuchi, H Umezawa J Antibiot (Tokyo). 1987 Dec;40(12):1740-5. doi: 10.7164/antibiotics.40.1740.
Biosynthetic studies on napyradiomycins were carried out based on the incorporation of [2-13C]acetate and [1,2-13C]acetate. The alignment of acetate units suggested that the B and C rings of napyradiomycins are derived from a pentaketide, while ring A and the side chain may be synthesized from mevalonate.
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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 ╳
