Manumycin G
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| Category | Antibiotics |
| Catalog number | BBF-02297 |
| CAS | 156250-44-1 |
| Molecular Weight | 506.55 |
| Molecular Formula | C28H30N2O7 |
| Purity | ≥95% |
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Description
It is produced by the strain of Str. sp. WB-83. It has anti-gram-positive bacteria and Escherichia coli effects, but the effect is very weak against other anti-gram-negative bacteria, and has no effect on fungi. It inhibits RAS Faraday base transfer with IC50 of 5 μmol/L. It has weak cytotoxic activity against human cloned cancer cell lines HCT-116 (IC50 is 15.6 μg/mL).
Specification
| Synonyms | 2,4,6-Nonatrienamide, N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-8-methyl-, (2E,4E,6E)-; 2,4,6-Nonatrienamide, N-[5-hydroxy-5-[7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-8-methyl-, [1S-[1a,3(2E,4E,6E),5b,5(1E,3E,5E),6a]]- |
| IUPAC Name | (2E,4E,6E)-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-8-methylnona-2,4,6-trienamide |
| Canonical SMILES | CC(C)C=CC=CC=CC(=O)NC1=CC(C2C(C1=O)O2)(C=CC=CC=CC(=O)NC3=C(CCC3=O)O)O |
| InChI | InChI=1S/C28H30N2O7/c1-18(2)11-7-3-4-8-12-22(33)29-19-17-28(36,27-26(37-27)25(19)35)16-10-6-5-9-13-23(34)30-24-20(31)14-15-21(24)32/h3-13,16-18,26-27,31,36H,14-15H2,1-2H3,(H,29,33)(H,30,34)/b4-3+,6-5+,11-7+,12-8+,13-9+,16-10+/t26-,27-,28+/m1/s1 |
| InChI Key | WIFRXHSYMJBOJD-WRSGMFNISA-N |
Properties
| Appearance | Yellow Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor) |
| Boiling Point | 876.1±65.0°C (Predicted) |
| Melting Point | >250°C (dec.) |
| Density | 1.32±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Acetonitrile |
Reference Reading
1. Manumycins E, F and G, new members of manumycin class antibiotics, from Streptomyces sp
Y Z Shu, S Huang, R R Wang, K S Lam, S E Klohr, K J Volk, D M Pirnik, J S Wells, P B Fernandes, P S Patel J Antibiot (Tokyo). 1994 Mar;47(3):324-33. doi: 10.7164/antibiotics.47.324.
Three new manumycin class antibiotics, namely manumycins E, F and G, were isolated from the culture broth of Streptomyces sp. strain WB-8376. Their structures were established by spectroscopic methods, and the S configuration of C-4 in the epoxycyclohexenone moiety was determined by CD exciton chirality method for each of the three compounds. Manumycins E, F and G are active against Gram-positive bacteria, and have moderate inhibitory effects on the farnesylation of p21 ras protein. They demonstrated weak cytotoxic activity against human colon tumor cell HCT-116.
2. EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme inhibitors produced by Streptomyces sp. E-1511 and E-1625. III. Biochemical properties of EI-1511-3, -5 and EI-1625-2
T Tanaka, E Tsukuda, Y Uosaki, Y Matsuda J Antibiot (Tokyo). 1996 Nov;49(11):1085-90. doi: 10.7164/antibiotics.49.1085.
EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme (ICE) inhibitors from the culture broths of Streptomyces sp. selectively inhibited the recombinant human ICE activity with IC50 values of 0.09, 0.38 and 0.2 microM, respectively, without inhibiting elastase and cathepsin B. Manumycin G, ent-alisamycin, U-56,407, and manumycin A and B isolated simultaneously from the same strains also inhibited ICE. EI-1511-3, -5 and EI-1625-2 also inhibited mature interleukin-1 beta secretion from THP-1 cells with IC50 values of 5.4, 3.6 and 2.2 microM, respectively. In this article, biological properties of EI-1511-3, -5 and EI-1625-2 and, in addition, properties of manumycin-related compound are described.
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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 ╳
