NK30424A
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| Category | Bioactive by-products |
| Catalog number | BBF-03298 |
| CAS | |
| Molecular Weight | 626.8 |
| Molecular Formula | C30H46N2O10S |
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Description
NK30424A is an inhibitor of lipopolysaccharide-induced tumour necrosis factor alpha production with IC50 value of 1 µmol/L. It is produced by Streptomyces sp. NA30424.
Specification
| IUPAC Name | 2-amino-3-[[(7Z)-12-[(E)-8-(2,6-dioxopiperidin-4-yl)-7-hydroxy-4-methyl-5-oxooct-2-en-2-yl]-10-hydroxy-9-methoxy-11-methyl-2-oxo-1-oxacyclododec-7-en-4-yl]sulfanyl]propanoic acid |
| Canonical SMILES | CC1C(C(C=CCCC(CC(=O)OC1C(=CC(C)C(=O)CC(CC2CC(=O)NC(=O)C2)O)C)SCC(C(=O)O)N)OC)O |
| InChI | InChI=1S/C30H46N2O10S/c1-16(23(34)13-20(33)10-19-11-25(35)32-26(36)12-19)9-17(2)29-18(3)28(38)24(41-4)8-6-5-7-21(14-27(37)42-29)43-15-22(31)30(39)40/h6,8-9,16,18-22,24,28-29,33,38H,5,7,10-15,31H2,1-4H3,(H,39,40)(H,32,35,36)/b8-6-,17-9+ |
| InChI Key | JOTZTCRQORWZKM-DZCRTHFOSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 129-131°C |
Reference Reading
1. Iso-migrastatin congeners from Streptomyces platensis and generation of a glutarimide polyketide library featuring the dorrigocin, lactimidomycin, migrastatin, and NK30424 scaffolds
Jianhua Ju, Si-Kyu Lim, Hui Jiang, Jeong-Woo Seo, Ben Shen J Am Chem Soc. 2005 Aug 31;127(34):11930-1. doi: 10.1021/ja053118u.
Iso-Migrastatin (10) has been shown to be the main natural product of Streptomyces platensis, which undergoes a facile, H2O-mediated rearrangement into dorrigocin A (2), 13-epi-dorrigocin A (11), dorrigocin B (3), and migrastatin (1). Eight new congeners (12-19) of 10 were characterized. They can undergo the same H2O-mediated rearrangement into the corresponding 1, 2, 3, and 11 analogues (20-43) or 1,4-Michael addition with cysteine to afford the corresponding analogues (44-51) of NK30424 A and B (5, 6). This study generated a 47-member library of glutarimide polyketides, setting the stage to investigate the SAR for this family of natural products. These results also established the absolute stereochemistry of 5 and 6 and shed new light into the post-polyketide synthase steps for 10 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 ╳
