Sarubicin B
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| Category | Antibiotics |
| Catalog number | BBF-02886 |
| CAS | 84745-01-7 |
| Molecular Weight | 258.23 |
| Molecular Formula | C13H10N2O4 |
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Description
It is produced by the strain of Str. violaceoruber sp. JA 2861. It has anti-gram-positive bacteria effect, but no anti-gram-negative bacteria, fungi and yeast effects.
Specification
| Synonyms | 2-Naphthalenecarboxamide, 5-acetyl-3-amino-1,4-dihydro-1,4-dioxo- |
| IUPAC Name | 5-acetyl-1-hydroxy-3-imino-4-oxonaphthalene-2-carboxamide |
| Canonical SMILES | CC(=O)C1=CC=CC2=C1C(=O)C(=N)C(=C2O)C(=O)N |
| InChI | InChI=1S/C13H10N2O4/c1-5(16)6-3-2-4-7-8(6)12(18)10(14)9(11(7)17)13(15)19/h2-4,14,17H,1H3,(H2,15,19) |
| InChI Key | YKJQUOFKMCKKGM-UHFFFAOYSA-N |
Properties
| Appearance | Orange Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 540.6°C at 760 mmHg |
| Melting Point | 282-284°C |
| Density | 1.466 g/cm3 |
| Solubility | Soluble in Methanol, DMSO, Benzene |
Reference Reading
1. Sarubicin b, a new quinone antibiotic, isolated from the fermentation broth of a streptomyces strain
K Eckardt, D Tresselt, W Ihn, G Bradler, G Reinhardt J Antibiot (Tokyo). 1982 Dec;35(12):1638-40. doi: 10.7164/antibiotics.35.1638.
Sarubicin B, isolated from the culture filtrate of a Streptomyces strain JA 2861, is a new quinone antibiotic. The compound was isolated as an orange crystalline powder, mp 282 approximately 284 degrees C. In vitro sarubicin B was found to inhibit Gram-positive bacteria. It was not active against Gram-negative microorganisms.
2. Sarubicinols A-C, Cytotoxic Benzoxazoles from a Streptomyces
Han Wang, Huan Qi, Shao-Yong Zhang, Wen-Shuai Song, Li-Qin Zhang, Wen-Sheng Xiang, Ji-Dong Wang J Nat Prod. 2022 Apr 22;85(4):1167-1173. doi: 10.1021/acs.jnatprod.1c00820. Epub 2022 Feb 25.
A chemical investigation of Streptomyces sp. Hu186 afforded two known quinone antibiotics, sarubicin A (1) and sarubicin B (2), together with three unusual variants, sarubicinols A-C (3-5), and two new 1,4-naphthoquinone metabolites, sarubicin B1 (6) and sarubicin B2 (7). Compounds 3-5 possess a rare 2-oxabicyclo [2.2.2] substructure and a benzoxazole ring system. Their structures were elucidated using 1D and 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data. The absolute configurations of the side-chain moieties in 4 and 5 were solved by electronic circular dichroism calculations. Compounds 1-7 showed moderate cytotoxic activity against four tumor cell lines.
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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 ╳
