A-500359 M-2
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| Category | Antibiotics |
| Catalog number | BBF-03181 |
| CAS | |
| Molecular Weight | 601.58 |
| Molecular Formula | C23H31N5O12S |
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Description
A-500359 M-2 is a bacterial translocase-1 (Translocase I, EC 2.7. 8.13) inhibitor produced by Streptomyces griseus SANK 60196. It has activity against Mycobacterium smegmatis, Streptococcus pneumoniae and Streptococcus pyogenes, with an MIC of 6.25-12.5 µg/mL.
Specification
| Synonyms | N-((3R,6R)-3-Methyl-5-oxo(1,4-thiazaperhydroepin-6-yl))(6-{[(2S,3S,4R,5R)-5-(2,4-dioxo(1,3-dihydropyrimidinyl))-4-hydroxy-3-methoxyoxolan-2-yl]carbamoylmethoxy}(4S,5S,6S)-4,5-dihydroxy(4H-5,6-dihydropyran-2-yl))carboxamide |
| IUPAC Name | (2S,3S,4S)-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-N-[(3R,6R)-3-methyl-5-oxo-1,4-thiazepan-6-yl]-3,4-dihydro-2H-pyran-6-carboxamide |
| Canonical SMILES | CC1CSCC(C(=O)N1)NC(=O)C2=CC(C(C(O2)OC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)OC)C(=O)N)O)O |
| InChI | InChI=1S/C23H31N5O12S/c1-8-6-41-7-9(19(34)25-8)26-20(35)11-5-10(29)13(31)22(38-11)40-17(18(24)33)16-15(37-2)14(32)21(39-16)28-4-3-12(30)27-23(28)36/h3-5,8-10,13-17,21-22,29,31-32H,6-7H2,1-2H3,(H2,24,33)(H,25,34)(H,26,35)(H,27,30,36)/t8-,9+,10+,13+,14-,15+,16+,17-,21-,22-/m1/s1 |
| InChI Key | CZGXONQQLSSPKM-FYUGBLSDSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. Studies on novel bacterial translocase I inhibitors, A-500359s. III. Deaminocaprolactam derivatives of capuramycin: A-500359 E, F, H; M-1 and M-2
Yasunori Muramatsu, Shunichi Miyakoshi, Yasumasa Ogawa, Takashi Ohnuki, Michiko Miyazawa Ishii, Masatoshi Arai, Toshio Takatsu, Masatoshi Inukai J Antibiot (Tokyo). 2003 Mar;56(3):259-67. doi: 10.7164/antibiotics.56.259.
Novel derivatives of capuramycin were obtained when 10 mM of 2-aminoethyl-L-cysteine (AEC), an inhibitor of aspartokinase, was added to the culture of Streptomyces griseus SANK 60196, the producer of A-500359. They were purified from the culture filtrate and their chemical structures were elucidated as a deaminocaprolactam derivative of capuramycin designated as A-500359 F, A-500359 E, a methyl ester of A-500359 F, and A-500359 H, a 3'-demethyl derivative of A-500359 F. Two other compounds, A-500359 M-1 and A-500359 M-2, were purified from the same medium and their structures were elucidated. A-500359 E, F, H, M-1 and M-2 inhibited bacterial translocase I with an IC50 of 0.027 microM, 1.1 microM, 0.008 microM, 0.058 microM and 0.010 microM, respectively. A-500359 E, M-1 and M-2 inhibited the growth of mycobacteria as well.
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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 ╳
