Brasiliquinone A
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| Category | Antibiotics |
| Catalog number | BBF-00174 |
| CAS | 183201-02-7 |
| Molecular Weight | 465.49 |
| Molecular Formula | C26H27NO7 |
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Description
Brasiliquinone A is a benzo-onionquinone antibiotic produced by Nocardia brasiliensis, which has anti-gram-positive bacteria and tumor activity.
Specification
| Synonyms | (3S)-3-ethyl-6-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydrotetraphen-8-yl 3-amino-2,3,6-trideoxy-alpha-L-ribo-hexopyranoside |
| IUPAC Name | (3S)-8-[(2S,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-6-hydroxy-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CCC1CC2=CC(=C3C(=C2C(=O)C1)C(=O)C4=C(C3=O)C(=CC=C4)OC5CC(C(C(O5)C)O)N)O |
| InChI | InChI=1S/C26H27NO7/c1-3-12-7-13-9-17(29)22-23(20(13)16(28)8-12)25(31)14-5-4-6-18(21(14)26(22)32)34-19-10-15(27)24(30)11(2)33-19/h4-6,9,11-12,15,19,24,29-30H,3,7-8,10,27H2,1-2H3/t11-,12-,15+,19-,24-/m0/s1 |
| InChI Key | GMELFDQPUZSJEE-XHBGPGOOSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Melting Point | 132-135°C |
| Solubility | Soluble in Methanol, chloroform, ethyl acetate, methyl ether |
Reference Reading
1. Brasiliquinones A, B and C, new benz[alpha]anthraquinone antibiotics from Nocardia brasiliensis. I. Producing strain, isolation and biological activities of the antibiotics
A Nemoto, Y Tanaka, Y Karasaki, H Komaki, K Yazawa, Y Mikami, T Tojo, K Kadowaki, M Tsuda, J Kobayashi J Antibiot (Tokyo). 1997 Jan;50(1):18-21. doi: 10.7164/antibiotics.50.18.
New benz[alpha]anthraquinone antibiotics (brasiliquinones A, B and C) with an ethyl group at C-3 were isolated. The producer was identified as Nocardia brasiliensis. The antibiotics were active against Gram-positive bacteria including Mycobacterium sp., but not active against Gram-negative bacteria or fungi. They were also active against multiple drug-resistant P388/ADR tumor cells.
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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 ╳
