daunomycinone profile

Daunomycinone is a key intermediate in the biosynthesis of the antitumor antibiotic daunorubicin. It is a highly complex molecule with a tetracyclic anthraquinone core and a sugar moiety. Research on daunomycinone focuses on understanding its biosynthesis, exploring its potential as an anticancer agent, and developing new synthetic methods for its production. The compound is studied due to its potent antitumor activity, which is attributed to its ability to intercalate into DNA and inhibit DNA replication. Daunomycinone has also been explored as a starting material for the synthesis of new anticancer drugs with improved therapeutic properties. Synthesis of daunomycinone involves a complex series of enzymatic reactions catalyzed by a variety of enzymes, including glycosyltransferases, oxidoreductases, and methyltransferases. The biosynthesis of daunomycinone is a fascinating example of how nature produces complex molecules with potent biological activity. The study of daunomycinone contributes to the development of new anticancer drugs and provides insights into the biosynthesis of complex natural products.'

daunomycinone: the aglycone of daunomycin; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	83843
CHEMBL ID	423953
SCHEMBL ID	118279
MeSH ID	M0071697

Synonym
daunomycinon
nsc-109351
21794-55-8
daunomycinone
ccris 7632
5,12-naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8s,10s)-
daunorubicinone
nsc 109351
inchi=1/c21h18o8/c1-8(22)21(28)6-10-13(11(23)7-21)19(26)16-15(18(10)25)17(24)9-4-3-5-12(29-2)14(9)20(16)27/h3-5,11,23,25-26,28h,6-7h2,1-2h3/t11-,21-/m0/s1
yofdhowpgulaqf-mqjdwespsa-
CHEMBL423953
(7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione
fn5680x78x ,
unii-fn5680x78x
epirubicin hydrochloride impurity b [ep impurity]
daunorubicin hydrochloride impurity a [ep impurity]
epirubicin hydrochloride impurity, daunorubicinone- [usp impurity]
(8s,10s)-8-acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
daunorubicinone [usp-rs]
SCHEMBL118279
YOFDHOWPGULAQF-MQJDWESPSA-N
AKOS027321940
J-014292
BCP07437
DTXSID50944400
Q27278086
(8s,10s)-8-acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	18 (78.26)	18.7374
1990's	2 (8.70)	18.2507
2000's	2 (8.70)	29.6817
2010's	1 (4.35)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	1 (4.35%)	4.05%
Observational	0 (0.00%)	0.25%
Other	22 (95.65%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
carmustine Carmustine: A cell-cycle phase nonspecific alkylating antineoplastic agent. It is used in the treatment of brain tumors and various other malignant neoplasms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p462) This substance may reasonably be anticipated to be a carcinogen according to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985). (From Merck Index, 11th ed). carmustine : A member of the class of N-nitrosoureas that is 1,3-bis(2-chloroethyl)urea in which one of the nitrogens is substituted by a nitroso group.	1.96	1	N-nitrosoureas; organochlorine compound	alkylating agent; antineoplastic agent
streptonigrin [no description available]	1.96	1	pyridines; quinolone	antimicrobial agent; antineoplastic agent
mitomycin Mitomycin: An antineoplastic antibiotic produced by Streptomyces caespitosus. It is one of the bi- or tri-functional ALKYLATING AGENTS causing cross-linking of DNA and inhibition of DNA synthesis.. mitomycin : A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.	1.96	1	mitomycin	alkylating agent; antineoplastic agent
cytarabine [no description available]	2.06	1	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.01	1	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	4.05	15	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
trifluoroacetamide [no description available]	1.97	1
rhodomycinone rhodomycinone: anthracycline antibiotic. epsilon-rhodomycinone : A carboxylic ester that is the methyl ester of (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid.	7.88	4	carbopolycyclic compound; methyl ester; polyphenol; tetracenequinones; tetracenomycin
aklavinone aklavinone: from Streptomyces galilaeus MA 144-M1, strain 3AR-33; structure in first source	6.95	1	anthracycline; methyl ester; tertiary alcohol; tetracenequinones	antineoplastic agent
carminomycinone carminomycinone: aglycone of carminomycin	1.95	1
nogalamycin Nogalamycin: An anthrocycline from a Streptomyces nogalater variant. It is a cytolytic antineoplastic that inhibits DNA-dependent RNA synthesis by binding to DNA.. nogalamycin : An anthracycline antibiotic isolated from Streptomyces nogalater. It is a DNA intercalator and exhibits anticancer properties.	1.96	1
daunorubicinol daunorubicinol: main metabolite of daunomycin. (13S)-13-dihydrodaunorubicin : The (13S)-diastereomer of 13-dihydrodaunorubicin.	2.37	2	13-dihydrodaunorubicin
nadp [no description available]	1.96	1
adriamycin aglycone adriamycin aglycone: RN given refers to (8S-cis)-isomer	2.37	2
carubicin Carubicin: A very toxic anthracycline-type antineoplastic related to DAUNORUBICIN, obtained from Actinomadura carminata.. carminomycin(1+) : An anthracyline cation that is the conjugate acid of carminomycin, obtained by protonation of the amino group.	2.36	2	anthracycline cation

Condition	Relationship Strength	Studies
Recrudescence [description not available]	2.06	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.06	1
Di Guglielmo Disease [description not available]	2.06	1
Monosomy The condition in which one chromosome of a pair is missing. In a normally diploid cell it is represented symbolically as 2N-1.	2.06	1
Leukemia, Pre-B-Cell [description not available]	2.06	1
Chromosome Deletion Actual loss of portion of a chromosome.	2.06	1
Acute Disease Disease having a short and relatively severe course.	2.4	2
Leukemia, Erythroblastic, Acute A myeloproliferative disorder characterized by neoplastic proliferation of erythroblastic and myeloblastic elements with atypical erythroblasts and myeloblasts in the peripheral blood.	2.06	1
Precursor B-Cell Lymphoblastic Leukemia-Lymphoma A leukemia/lymphoma found predominately in children and adolescents and characterized by a high number of lymphoblasts and solid tumor lesions. Frequent sites involve LYMPH NODES, skin, and bones. It most commonly presents as leukemia.	2.06	1
Anoxemia [description not available]	1.96	1
Sarcoma 180 An experimental sarcoma of mice.	1.96	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	1.96	1
African Sleeping Sickness [description not available]	1.98	1
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	1.98	1
Leukemia P388 An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.	2.37	2
Leucocythaemia [description not available]	1.97	1
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	1.97	1
Leukemia L 1210 [description not available]	1.97	1

daunomycinone

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Studies (23)

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Research Demand Index: 18.64

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