Virantmycin
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| Category | Antibiotics |
| Catalog number | BBF-03471 |
| CAS | 76417-04-4 |
| Molecular Weight | 351.87 |
| Molecular Formula | C19H26C1NO3 |
| Purity | 99% |
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Description
It is produced by the strain of Str. nitrosporeus AM-2722. It has antiviral effect. It inhibits four RNA viruses and four DNA viruses with MIC (μg/mL) of 0.008-0.04 and 0.005-0.03, respectively. It has weak antifungal effect.
Specification
| Synonyms | 6-Quinolinecarboxylic acid, 3-chloro-2-(3,4-dimethyl-3-penten-1-yl)-1,2,3,4-tetrahydro-2-(methoxymethyl)-, (2R,3R)-; NSC 374127; 6-Quinolinecarboxylic acid, 3-chloro-2-(3,4-dimethyl-3-pentenyl)-1,2,3,4-tetrahydro-2-(methoxymethyl)-, (2R-cis)-; (-)-Virantmycin |
| IUPAC Name | (2R,3R)-3-chloro-2-(3,4-dimethylpent-3-enyl)-2-(methoxymethyl)-3,4-dihydro-1H-quinoline-6-carboxylic acid |
| Canonical SMILES | CC(=C(C)CCC1(C(CC2=C(N1)C=CC(=C2)C(=O)O)Cl)COC)C |
| InChI | InChI=1S/C19H26ClNO3/c1-12(2)13(3)7-8-19(11-24-4)17(20)10-15-9-14(18(22)23)5-6-16(15)21-19/h5-6,9,17,21H,7-8,10-11H2,1-4H3,(H,22,23)/t17-,19-/m1/s1 |
| InChI Key | FWINDTDIQJWMLC-IEBWSBKVSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Fungi; Viruses |
| Boiling Point | 506.7±50.0°C at 760 mmHg |
| Melting Point | 59°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Studies on novel HIF activators, A-503451s.I. Producing organism, fermentation, isolation and structural elucidation
Yuki Hirota-Takahata, Hideki Kobayashi, Masaaki Kizuka, Takao Ohyama, Michiko Kitamura-Miyazaki, Yasuhiro Suzuki, Mie Fujiwara, Mutsuo Nakajima, Osamu Ando J Antibiot (Tokyo). 2016 Oct;69(10):747-753. doi: 10.1038/ja.2016.17. Epub 2016 Mar 9.
In the course of our screening for activators of hypoxia-inducible factor (HIF), A-503451 A and virantmycin were isolated from the cultured broth of an actinomycete strain, Streptomyces sp. SANK 60101. From the same culture, the non-active homologs A-503451 B and D were also isolated. A-503451 A and virantmycin activated HIF-dependent reporter gene expression with EC50 values of 8 and 17 ng ml-1, respectively. They are highly potent activators of HIF and thus may be therapeutically useful for erythropoiesis and neural cell protection.
2. New tetrahydroquinoline and indoline compounds containing a hydroxy cyclopentenone, virantmycin B and C, produced by Streptomyces sp. AM-2504
Tōru Kimura, Takuya Suga, Masanori Kameoka, Minoru Ueno, Yuki Inahashi, Hirotaka Matsuo, Masato Iwatsuki, Katsumi Shigemura, Kazuro Shiomi, Yōko Takahashi, Satoshi Ōmura, Takuji Nakashima J Antibiot (Tokyo). 2019 Mar;72(3):169-173. doi: 10.1038/s41429-018-0117-0. Epub 2018 Dec 10.
Two new antibiotics, designated virantmycin B (1) and C (2), were isolated from the cultured broth of Streptomyces sp. AM-2504. Compounds 1 and 2 were purified by Diaion HP-20, silica gel, and octadecylsilane chromatography, followed by high-performance liquid chromatography. The chemical structures of the new compounds, 1 and 2, were determined by nuclear magnetic resonance and mass spectrometry, as containing a terahydroquinoline and an indoline, respectively, each also containing a hydroxy cyclopentenone moiety. Both compounds demonstrated weak antimicrobial (both antibacterial and antifungal) activity and compound 1 also showed antiviral activity against the dengue virus, whereas compound 2 exhibited no antiviral properties.
3. Antiviral Activity of Benzoheterocyclic Compounds from Soil-Derived Streptomyces jiujiangensis NBERC-24992
Manli Liu, Mengyao Ren, Yani Zhang, Zhongyi Wan, Yueyin Wang, Zhaoyuan Wu, Kaimei Wang, Wei Fang, Xiliang Yang Molecules. 2023 Jan 15;28(2):878. doi: 10.3390/molecules28020878.
Pseudorabies virus (PRV) is a pathogen that causes Aujeszky's disease (AD) in animals, leading to huge economic losses to swine farms. In order to discover anti-PRV compounds, we studied the extracts of the strain Streptomyces jiujiangensis NBERC-24992, which showed significant anti-PRV activity. Eight benzoheterocyclic secondary metabolites, including three new compounds (1-3, virantmycins D-G) and five known compounds (4-8, virantmycin, A-503451 D, A-503451 D acetylate, A-503451 A, and A-503451 B), were isolated from the broth of NBERC-24992. The structures of the new compounds were identified by using extensive spectroscopic data, including mass spectrometry (MS), nuclear magnetic resonance (NMR), and electronic circular dichroism (ECD). Compound 1 was found to be a novel heterocyclic compound with a tricyclic skeleton from natural product. All compounds were tested for antiviral activity, and 4 (virantmycin) showed an excellent effect against PRV and was better than ribavirin and acyclovir. Our study revealed that chlorine atom and tetrahydroquinoline skeleton were important active moiety for antiviral activity. Virantmycin could be a suitable leading compound for an antiviral drug against PRV.
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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 ╳
