A-500359A

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Category Antibiotics
Catalog number BBF-03173
CAS 254449-20-2
Molecular Weight 583.54
Molecular Formula C24H33N5O12

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Description

A-500359A is a bacterial translocase-1 (Translocase I, EC 2.7. 8.13) inhibitor produced by Streptomyces griseus SANK 60196. It has the activity of inhibiting translocase-1, IC50 is 0.017 µmol/L, and the IC50 of inhibiting peptidoglycan biosynthesis is 0.68 µmol/L. It also has activity against Mycobacterium smegmatis, Streptococcus pneumoniae and Streptococcus pyogenes, with an MIC of 6.25-12.5 µg/mL.

Specification

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-[(3S,7R)-7-methyl-2-oxoazepan-3-yl]-3,4-dihydro-2H-pyran-6-carboxamide
Canonical SMILES CC1CCCC(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/C24H33N5O12/c1-9-4-3-5-10(20(35)26-9)27-21(36)12-8-11(30)14(32)23(39-12)41-18(19(25)34)17-16(38-2)15(33)22(40-17)29-7-6-13(31)28-24(29)37/h6-11,14-18,22-23,30,32-33H,3-5H2,1-2H3,(H2,25,34)(H,26,35)(H,27,36)(H,28,31,37)/t9-,10+,11+,14+,15-,16+,17+,18-,22-,23-/m1/s1
InChI Key RVEJXOKUHHMFKS-BPJITGRLSA-N

Properties

Appearance Powder
Antibiotic Activity Spectrum Gram-positive bacteria; mycobacteria
Density 1.6±0.1 g/cm3

Reference Reading

1. Synthesis and antimycobacterial activity of capuramycin analogues. Part 2: acylated derivatives of capuramycin-related compounds
Hitoshi Hotoda, Makiko Daigo, Miyuki Furukawa, Kazuhiro Murayama, Chikako Akiyama Hasegawa, Masakatsu Kaneko, Yasunori Muramatsu, Michiko Miyazawa Ishii, Shun-ichi Miyakoshi, Toshio Takatsu, Masatoshi Inukai, Masayo Kakuta, Tomomi Abe, Takashi Fukuoka, Yukio Utsui, Satoshi Ohya Bioorg Med Chem Lett. 2003 Sep 1;13(17):2833-6. doi: 10.1016/s0960-894x(03)00597-3.
Acylated derivatives of capuramycin and A-500359A were synthesized and tested for antimycobacterial activity. Compound 20 having a decanoyl group showed very potent activity.

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* 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

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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