10'-Desmethoxystreptonigrin
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| Category | Antibiotics |
| Catalog number | BBF-01834 |
| CAS | 136803-89-9 |
| Molecular Weight | 476.44 |
| Molecular Formula | C24H20N4O7 |
| Purity | >95% by HPLC |
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Description
It is a close analogue of streptonigrin produced by selected streptomyces species. It is a moderately potent inhibitor of farnesylation of RAS P21 protein, 3-fold more active than streptonigrin. It has potent and broad spectrum antibacterial and antitumour activity.
Specification
| Synonyms | 2-Pyridinecarboxylic acid, 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3-methoxyphenyl)-3-methyl-; 10-Desmethoxystreptonigrin |
| Storage | Store at -20°C |
| IUPAC Name | 5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3-methoxyphenyl)-3-methylpyridine-2-carboxylic acid |
| Canonical SMILES | CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)N)OC)N)C4=C(C(=CC=C4)OC)O |
| InChI | InChI=1S/C24H20N4O7/c1-9-14(10-5-4-6-13(34-2)20(10)29)15(25)19(28-17(9)24(32)33)12-8-7-11-18(27-12)22(31)16(26)23(35-3)21(11)30/h4-8,29H,25-26H2,1-3H3,(H,32,33) |
| InChI Key | ULSNCNUVHUNMCF-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Red Brown Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Bacteria |
| Boiling Point | 683.6°C at 760 mmHg |
| Density | 1.55 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. 10'-Desmethoxystreptonigrin, a novel analog of streptonigrin
J M Clark, P B Fernandes, A R Crosswell, T W Doyle, M Bulgar, W C Liu, L Dean, S Huang, V Manne, M Barbacid J Antibiot (Tokyo) . 1992 Apr;45(4):454-7. doi: 10.7164/antibiotics.45.454.
10'-Desmethoxystreptonigrin, a novel analog of streptonigrin produced by Streptomyces albus, was discovered in a screen for inhibitors of farnesylation of RAS p21 protein. The compound was isolated from the fermentation broth and its structure determined. It is markedly cytotoxic to several human tumor cell lines and also exhibits potent broad-spectrum antibacterial activity.
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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 ╳
