Neihumicin
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| Category | Antibiotics |
| Catalog number | BBF-02108 |
| CAS | 111451-12-8 |
| Molecular Weight | 304.34 |
| Molecular Formula | C19H16N2O2 |
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Description
Neihumicin is produced by the strain of Micromonospora neihuensis Wu, sp. nov. Neihumicin is resistant to beer saccharomyces yeast and Penicillium italium Wehmer, but not to bacteria.
Specification
| Synonyms | Neihumycin; 3,6-Dibenzylidene-2-methoxy-3,6-dihydropyrazin-5-one; NSC617674; (Z,Z)-3,6-Dihydro-5-methoxy-3,6-bis(phenylmethylene)-2(1H)-pyrazinone |
| IUPAC Name | (3Z,6Z)-3,6-dibenzylidene-5-methoxypyrazin-2-one |
| Canonical SMILES | COC1=NC(=CC2=CC=CC=C2)C(=O)NC1=CC3=CC=CC=C3 |
| InChI | InChI=1S/C19H16N2O2/c1-23-19-17(13-15-10-6-3-7-11-15)20-18(22)16(21-19)12-14-8-4-2-5-9-14/h2-13H,1H3,(H,20,22)/b16-12-,17-13- |
| InChI Key | CKMSPKVRKZDILM-MCOFMCJXSA-N |
Properties
| Appearance | Yellow Crystals |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 175-176°C |
| Density | 1.14 g/cm3 |
Reference Reading
1. Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. I. The producing organism, fermentation, isolation and biological properties
R Y Wu, L M Yang, T Yokoi, K H Lee J Antibiot (Tokyo). 1988 Apr;41(4):481-7. doi: 10.7164/antibiotics.41.481.
A new cytotoxic and antifungal antibiotic, neihumicin, was isolated from the culture broth of a soil isolate identified as Micromonospora neihuensis Wu, sp. nov. Neihumicin shows in vitro cytotoxicity against KB tissue culture cells (ED50 0.94 micrograms/ml) as well as antifungal activity against Saccharomyces cerevisiae ATCC 9763.
2. Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. III. Structure-activity relationships
T Yokoi, L M Yang, T Yokoi, R Y Wu, K H Lee J Antibiot (Tokyo). 1988 Apr;41(4):494-501. doi: 10.7164/antibiotics.41.494.
Structure-cytotoxicity relationships studies have indicated that the C-3 and C-6 disubstituted piperazine-2,5-diones are structurally required for significant cytotoxicity, and the neihumicin-like C-3 and C-6 disubstituted unsymmetrical piperazine derivatives are, in general, more cytotoxic than the corresponding symmetrical piperazine-2,5-diones. Several synthetic analogs including 3,6-di-(2,4,5-trimethoxybenzylidene)piperazine-2,5- dione, 3,6-dibenzylidene-2-ethoxy-3,6-dihydropyrazine-5-one, 3-benzylidene-6-(m-chlorobenzylidene)-2-methoxy-3,6-dihydropyrazine++ +-5-one, have been shown to be more cytotoxic than neihumicin.
3. Neihumicin, a new cytotoxic antibiotic from Micromonospora neihuensis. II. Structural determination and total synthesis
L M Yang, R Y Wu, A T McPhail, T Yokoi, K H Lee J Antibiot (Tokyo). 1988 Apr;41(4):488-93. doi: 10.7164/antibiotics.41.488.
The structure of neihumicin, a new antibiotic isolated from the fermentation broth of Micromonospora neihuensis Wu, sp. nov., has been determined as (Z)-3,(Z)-6-dibenzylidene-2-methoxy-3,6-dihydropyrazin-5-one based upon spectral evidence and X-ray crystallographic analysis. Its total synthesis has also been achieved.
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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 ╳
