Compounds > rhodomycinone
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rhodomycinone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Rhodomycinone is a potent antitumor antibiotic produced by the bacterium Streptomyces purpurascens. It is known for its complex structure, which includes a highly oxygenated anthraquinone core. The compound exhibits a wide range of biological activities, including cytotoxic activity against several cancer cell lines. Notably, rhodomycinone has shown promising anticancer effects in preclinical studies, with potential applications in treating leukemia, lymphoma, and breast cancer. The synthesis of rhodomycinone remains a significant challenge due to its intricate molecular architecture. Researchers are actively investigating various approaches to synthesizing rhodomycinone, including biocatalytic methods and total synthesis strategies. The understanding of rhodomycinone's biosynthesis and its potential anticancer properties has sparked considerable research interest in the development of new antitumor agents. Studying rhodomycinone is crucial for exploring its therapeutic potential and understanding the mechanisms of action underlying its biological effects. The complex structure of this compound also serves as a fascinating target for synthetic chemistry research, pushing the boundaries of organic synthesis and providing valuable insights into molecular complexity.'

rhodomycinone: anthracycline antibiotic [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID99207
CHEMBL ID22025
CHEBI ID75291
MeSH IDM0064788

Synonyms (14)

Synonym
21288-60-8
epsilon-rhodomycinone
rhodomycinone
e-rhodomycinone
chebi:75291 ,
CHEMBL22025
AC1L40QH ,
methyl (1r,2r,4s)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylate
AKOS004902751
1-naphthacenecarboxylic acid, 2-ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7,12-pentahydroxy-6,11-dioxo-, methyl ester, (1r-(1alpha,2beta,4beta))-
nsc 196524
methyl (1r,2r,4s)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
Q27105038
epsilon-rhodomycinon
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (5)

ClassDescription
tetracenomycinA polyketide based on a tetracene ring structure.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
carbopolycyclic compoundA polyclic compound in which all of the ring members are carbon atoms.
tetracenequinones
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
daunorubicin biosynthesis1930

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1354667Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces.
AID70892Compound is evaluated for lambda-phage induction activity in Escherichia coli (dose at 50 ug/mL); Toxic to culture1980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
8-Hydroxyanthracyclinones from epsilon-rhodomycinone.
AID333401Antibacterial activity against Bacillus subtilis ATCC 6633 after 24 hrs by microtiter plate assay2004Journal of natural products, Oct, Volume: 67, Issue:10
Blanchaquinone: a new anthraquinone from an Australian Streptomyces sp.
AID70889Compound is evaluated for lambda-phage induction activity in Escherichia coli (dose at 25 ug/mL)1980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
8-Hydroxyanthracyclinones from epsilon-rhodomycinone.
AID1354666Cytotoxicity against human HCT116 cells after 48 hrs by MTT assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces.
AID1354668Cytotoxicity against human MCF10A cells after 48 hrs by MTT assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces.
AID1354664Cytotoxicity against human NCI-H460 cells after 48 hrs by MTT assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces.
AID70888Compound is evaluated for lambda-phage induction activity in Escherichia coli (dose at 12.5 ug/mL)1980Journal of medicinal chemistry, Nov, Volume: 23, Issue:11
8-Hydroxyanthracyclinones from epsilon-rhodomycinone.
AID1354663Cytotoxicity against human MDA-MB-435 cells after 48 hrs by MTT assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces.
AID1354665Cytotoxicity against human MDA-MB-231 cells after 48 hrs by MTT assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Cytotoxic Anthracycline Metabolites from a Recombinant Streptomyces.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (29.03)18.7374
1990's9 (29.03)18.2507
2000's6 (19.35)29.6817
2010's6 (19.35)24.3611
2020's1 (3.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (6.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other29 (93.55%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethyl methanesulfonate
Ethyl Methanesulfonate: An antineoplastic agent with alkylating properties. It also acts as a mutagen by damaging DNA and is used experimentally for that effect.. ethyl methanesulfonate : A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.		1.9710methanesulfonate esteralkylating agent;
antineoplastic agent;
carcinogenic agent;
genotoxin;
mutagen;
teratogenic agent
naphthacene
tetracene : An acene that consists of four ortho-fused benzene rings in a rectilinear arrangement.		2.1710acene;
tetracenes
funiculosin (anthraquinone)
funiculosin (anthraquinone): see also a pyridone cpd called funiculosin; structure		2.730trihydroxyanthraquinone
nitrosoguanidines
Nitrosoguanidines: Nitrosylated derivatives of guanidine. They are used as MUTAGENS in MOLECULAR BIOLOGY research.		1.9710
rhamnose
[no description available]		710L-rhamnose
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.		8.93130aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
epirubicin
Epirubicin: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.		2.5120aminoglycoside;
anthracycline antibiotic;
anthracycline;
deoxy hexoside;
monosaccharide derivative;
p-quinones;
primary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone		antimicrobial agent;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
daunomycinone
daunomycinone: the aglycone of daunomycin; structure		7.8840
oxaunomycin
oxaunomycin: produced by blocked mutant of the daunorubicin-producing microorganism; structure given in first source		1.9810
aklavinone
aklavinone: from Streptomyces galilaeus MA 144-M1, strain 3AR-33; structure in first source		7.9140anthracycline;
methyl ester;
tertiary alcohol;
tetracenequinones		antineoplastic agent
ristosamine
ristosamine: aminosugar component of antibiotic ristomycin; RN given refers to (D-ribo)-isomer; see also acosamine, (L-arabino)-isomer: 41094-24-0 & daunosamine, (L-lyxo)-isomer: 26548-47-0; structure		710
daunosamine
daunosamine: amino sugar moiety common to adriamycin & daunomycin; RN given refers to (L-lyxo)-isomer; see also ristosamine, (L-ribo)-isomer: 51869-30-8 & acosamine, (L-arabino)-isomer: 41094-24-0; structure		9.0240
carubicin
carminomycin : A toxic anthracycline antibiotic that is produced by Actinomadura carminata and also has potent antineoplastic activity.		1.9510aminoglycoside antibiotic;
anthracycline antibiotic;
p-quinones;
tertiary alpha-hydroxy ketone;
tetracenequinones		antineoplastic agent;
apoptosis inducer
aclarubicin
Aclarubicin: An anthracycline produced by Streptomyces galilaeus. It has potent antineoplastic activity.. aclacinomycin A : An anthracycline antibiotic that is produced by Streptomyces galilaeus and also has potent antineoplastic activity.		2.3920aminoglycoside;
anthracycline;
methyl ester;
phenols;
polyketide;
tetracenequinones;
trisaccharide derivative;
zwitterion		antimicrobial agent;
antineoplastic agent;
apoptosis inducer;
bacterial metabolite;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
glycosides
[no description available]		9.250
malonyl coenzyme a
Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.		1.9710malonyl-CoAsEC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor;
Escherichia coli metabolite;
metabolite;
mouse metabolite
acosamine
acosamine: component of antibiotic actinodin; RN given refers to (L-arabino)-isomer; see also ristosamine, (L-ribo)-isomer: 51869-30-8 & daunosamine, (L-lyxo)-isomer: 26548-47-0. acosamine : A trideoxyhexose carrying a single amino substituent at position 3 and deoxygenated at positions 2, 3 and 6.		710amino monosaccharide;
trideoxyhexose derivative
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.		1.9910anthracycline cation
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Oat Cell
[description not available]		01.9810
Leukemia L 1210
[description not available]		01.9810
Cancer of Lung
[description not available]		01.9810
Lung Neoplasms
Tumors or cancer of the LUNG.		01.9810
Carcinoma, Small Cell
An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)		01.9810