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Ekatetrone

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Ekatetrone
Category Antibiotics
Catalog number BBF-01201
CAS 12794-19-3
Molecular Weight 367.31
Molecular Formula C19H13NO7

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Streptomyces aureofaciens. It can inhibit the protein and nucleic acid synthesis of Ehrlician ascites cancer cells, and has no anti-bacterial and anti-yeast effect.

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Synonyms (+)-2-(10,12-dihydroxy-3,6,11-trioxo-3,4,6,11-tetrahydro-1H-naphtho[2,3-g]isochromen-1-yl)acetamide; 1,8-Dihydroxy-2-(1'-hydroxy-2'-carbamoyl)ethyl-9,10-anthraquinone 3-acetic acid lactone; (+)-Ekatetrone; (+)-3,4,6,11-Tetrahydro-10,12-dihydroxy-3,6,11-trioxo-1H-anthra[2,3-c]pyran-1-acetamide
IUPAC Name 2-(10,12-dihydroxy-3,6,11-trioxo-1,4-dihydronaphtho[2,3-g]isochromen-1-yl)acetamide
Canonical SMILES C1C2=CC3=C(C(=C2C(OC1=O)CC(=O)N)O)C(=O)C4=C(C3=O)C=CC=C4O
InChI InChI=1S/C19H13NO7/c20-12(22)6-11-14-7(5-13(23)27-11)4-9-16(18(14)25)19(26)15-8(17(9)24)2-1-3-10(15)21/h1-4,11,21,25H,5-6H2,(H2,20,22)
InChI Key QZENCFIHIPLZMU-UHFFFAOYSA-N
Appearance Yellow Crystal
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 742.7±60.0 °C (Predicted)
Melting Point 270-272 °C (dec.)
Density 1.606±0.06 g/cm3 (Predicted)
Solubility Freely soluble in Acetic Acid, DMF; Slightly soluble in Methanol
1. The structure of ekatetrone, a metabolite of strains of Streptomyces aureofaciens
V Prikrylová, M Podojil, P Sedmera, J Vokoun, Z Vanĕk J Antibiot (Tokyo). 1978 Sep;31(9):855-62. doi: 10.7164/antibiotics.31.855.
The structure of ekatetrone has been determined from physico-chemical data obtained using the natural compound, its derivatives and products of degradation reactions. Ekatetrone was found to be the lactone of 1,8-dihydroxy-2-(1'-hydroxy-2'-carbamoyl)ethyl-9,10-anthraquinone-3-acetic acid (I). It is proposed that ekatetrone is related, biogenetically, to protetrone.
2. Isolation of ekatetrone, a new metabolite of producing variants of Streptomyces aureofaciens
M Podojil, Z Vanĕk, V Prikrylová, M Blumauerová J Antibiot (Tokyo). 1978 Sep;31(9):850-4. doi: 10.7164/antibiotics.31.850.
From a mixture of substances formed by producing strains of Streptomyces aureofaciens under conditions of submerged fermentation a new metabolite, ekatetrone, was isolated. Its isolation and basic physical and chemical data are described. Ekatetrone is a quinone derivative with a carboxamide group. In tests in vitro with cells of Ehrlich's ascites tumour evidence was provided that ekatetrone inhibits proteo- and nucleosynthesis.

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