Daunomycinone

Names

[ Name ]:
Daunomycinone

[Synonym ]:
5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S,10S)-
(8S,10S)-8-Acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-tetracenedione
daunomycinone
5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S-cis)-
(8S,10S)-8-Acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

Biological Activity

[Description]:

Daunomycinone (NSC-109351) is a metabolite of daunomycin. Daunomycin is an antibiotic with antitumor activity[1][2].

[Related Catalog]:

Research Areas >> Cancer

[References]

[1]. Herman EH, et al. Modification of some of the toxic effects of daunomycin (NSC-82,151) by pretreatment with the antineoplastic agent ICRF 159 (NSC-129,943). Toxicol Appl Pharmacol. 1974 Mar;27(3):517-26.

[2]. Tan C, et al. Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia. Cancer. 1967 Mar;20(3):333-53.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
677.4±55.0 °C at 760 mmHg

[ Melting Point ]:
208-210°C

[ Molecular Formula ]:
C₂₁H₁₈O₈

[ Molecular Weight ]:
398.36

[ Flash Point ]:
243.4±25.0 °C

[ Exact Mass ]:
398.100159

[ PSA ]:
141.36000

[ LogP ]:
2.93

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.713

[ Storage condition ]:
-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QI9295500

CHEMICAL NAME :: 5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1 -methoxy-, (8S, 10S)-

CAS REGISTRY NUMBER :: 21794-55-8

LAST UPDATED :: 199409

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H18-O8

MOLECULAR WEIGHT :: 398.39

WISWESSER LINE NOTATION :: L E6 C666 BV MVT&&&J DQ FQ HV1 HQ KQ RO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 2 umol/L

REFERENCE :: CHROAU Chromosoma. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1939- Volume(issue)/page/year: 68,115,1978

Safety Information

[ RIDADR ]:
UN 2811 6.1 / PGIII

Synthetic Route

Click to get detail synthetic route

Articles

Semiquinone free radical formation by daunorubicin aglycone incorporated into the cellular membranes of intact Chinese hamster ovary cells.

Free Radic. Res. 24(1) , 9-18, (1996)

The production of semiquinone free radicals has been measured by electron paramagnetic resonance spectroscopy (EPR) in Chinese hamster ovary cells in which 7-hydroxy daunorubicin aglycone had been inc...

Biotransformation of aklanonic acid by blocked mutants of anthracycline-producing strains of Streptomyces galilaeus and Streptomyces peucetius.

J. Basic Microbiol. 26(4) , 249-55, (1986)

Aklanonic acid is an anthracyclinone-related pigment that was found to be an intermediate at an early stage of the biosynthesis of daunomycinone glycosides by Streptomyces griseus. We now isolated ant...

Synthesis and biological activity of (7S)-O-epoxyalkyl derivatives of daunomycinone.

J. Antibiot. 38(12) , 1714-8, (1985)

Synthesis and antibacterial activity of a number of 7-O-epoxyalkyl derivatives of daunomycinone prepared from 7-O-alkenyl derivatives of daunomycinone are described along with their inhibitory effect ...