nanaomycin a profile

nanaomycin A: produced by a strain OS-3966 of Streptomyces rosa var. notoensis; quinone-related cpd; MF C16-H14-O6; see also nanaomycin B: 52934-85-7, nanaomycin C: 58286-55-8, nanaomycin E: 72660-52-7; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

nanaomycin A : A pyranonaphthoquinone antibiotic from strain OS-3966 of Streptomyces rosa var. notoensis. [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]

Related Flora

Flora	Rank	Flora Definition	Family	Family Definition
Rosa	genus	A plant genus in the family ROSACEAE and order Rosales. This should not be confused with the genus RHODIOLA which is sometimes called roseroot.[MeSH]	Rosaceae	The rose plant family in the order ROSALES and class Magnoliopsida. They are generally woody plants. A number of the species of this family contain cyanogenic compounds.[MeSH]

ID Source	ID
PubMed CID	442757
CHEMBL ID	2106789
CHEBI ID	48202
SCHEMBL ID	2111571
MeSH ID	M0052651

Synonym
bdbm50075103
nanaomycin a
nanomycin a
nanafrocine [french]
os-3966-a
(1s,3r)-3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-1h-naphtho-(2,3-c)pyran-3-acetic acid
nanafrocin [inn]
nanafrocinum [latin]
nsc 267461
antibiotic os 3966a
nanafrocina [spanish]
1h-naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-, (1s-e)-
nanafrocin
(1s,3r)-nanaomycin a
52934-83-5
[(1s,3r)-9-hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1h-benzo[g]isochromen-3-yl]acetic acid
[(1s,3r)-9-hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid
nanafrocine
rosanomycin a
nanafrocinum
CHEBI:48202 ,
CHEMBL2106789
nanafrocina
unii-8xbv72641v
8xbv72641v ,
nanafrocin [jan]
SCHEMBL2111571
1h-naphtho[2,3-c]pyran-3-acetic acid,3,4,5,10-tetrahydro-9-hydroxy-1-methyl-5,10-dioxo-(1s,3r)-
2-((1s,3r)-9-hydroxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1h-benzo[g]isochromen-3-yl)acetic acid
HY-103397
Q27104606
DTXSID401018642
CS-0027820
CCA93483
AKOS040742270

Excerpt	Reference	Relevance
"Nanaomycin A is an effective therapeutic candidate for treating neuroblastoma. "	( The DNMT3B Inhibitor Nanaomycin A as a Neuroblastoma Therapeutic Agent. Aoki, H; Aoyama, M; Hayashi, H; Inoue, Y; Izumi, K; Kakita, H; Takeshita, S; Ueda, H; Yamada, Y, 2023)	2.67

Excerpt	Reference	Relevance
"Nanaomycin A treatment reduced the global methylation levels in all three cell lines and reactivated transcription of the RASSF1A tumor suppressor gene."	( Nanaomycin A selectively inhibits DNMT3B and reactivates silenced tumor suppressor genes in human cancer cells. Caulfield, T; Kuck, D; Lyko, F; Medina-Franco, JL, 2010)	2.52

Excerpt	Reference	Relevance
" It was found that the antibiotic was well absorbed topically so that topical LD50 was approximately the same as intravenous LD50 in mice."	( [The therapeutic effect of nanaomycin A against experimental Trichophyton mentagrophytes infection in guinea pigs (author's transl)]. Araki, Y; Kitaura, K; Marumo, H, 1980)	0.56

Role	Description
bacterial metabolite	Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
[role 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]

Class	Description
benzoisochromanequinone	A class of Streptomyces aromatic polyketide antibiotics.
organooxygen heterocyclic antibiotic
p-quinones	A quinone in which the two oxo groups of the quinone are located para to each other on the 6-membered quinonoid ring.
monocarboxylic acid	An oxoacid containing a single carboxy group.
[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]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)	IC50 (µMol)	0.8075	0.2000	1.2164	7.5000	AID1199271; AID1649844; AID1649847; AID1649849
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
negative regulation of transcription by RNA polymerase II	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
positive regulation of gene expression	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
methylation	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
transcription corepressor activity	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
DNA (cytosine-5-)-methyltransferase activity	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
protein binding	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
DNA-methyltransferase activity	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
metal ion binding	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
DNA (cytosine-5-)-methyltransferase activity, acting on CpG substrates	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
DNA binding	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
nucleus	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
nucleoplasm	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
catalytic complex	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
nucleus	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Assay ID	Title	Year	Journal	Article
AID1649847	Inhibition of human recombinant DNMT3B expressed in baculovirus infected insect cells using CpG site containing internally quenched hairpin oligonucleotide DNA substrate and SAM incubated for 30 mins by kinetic fluorogenic assay	2020	ACS medicinal chemistry letters, May-14, Volume: 11, Issue:5	Structure-Guided Identification of DNMT3B Inhibitors.
AID1649849	Inhibition of human recombinant DNMT3B expressed in baculovirus infected insect cells by DRONE assay	2020	ACS medicinal chemistry letters, May-14, Volume: 11, Issue:5	Structure-Guided Identification of DNMT3B Inhibitors.
AID1649845	Toxicity in mouse	2020	ACS medicinal chemistry letters, May-14, Volume: 11, Issue:5	Structure-Guided Identification of DNMT3B Inhibitors.
AID1649846	Cytotoxicity in African green monkey Vero cells assessed as reduction in cell viability	2020	ACS medicinal chemistry letters, May-14, Volume: 11, Issue:5	Structure-Guided Identification of DNMT3B Inhibitors.
AID1199271	Inhibition of His6-tagged human recombinant DNMT3b expressed in insect Sf9 cells assessed as reduction in DNA methyltransferase activity using 5'-biotinylated 45-bp unmethylated or hemimethylated oligonucleotide substrates and [3H]-AdoMet by liquid scinti	2015	Journal of medicinal chemistry, Mar-26, Volume: 58, Issue:6	Targeting DNA methylation with small molecules: what's next?
AID1649844	Inhibition of human DNMT3B using [3H]-SAM	2020	ACS medicinal chemistry letters, May-14, Volume: 11, Issue:5	Structure-Guided Identification of DNMT3B Inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	9 (33.33)	18.7374
1990's	3 (11.11)	18.2507
2000's	3 (11.11)	29.6817
2010's	10 (37.04)	24.3611
2020's	2 (7.41)	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	1 (3.70%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	26 (96.30%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
hydroquinone [no description available]	2.03	1	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
procainamide Procainamide: A class Ia antiarrhythmic drug that is structurally-related to PROCAINE.. procainamide : A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.	3.21	1	benzamides	anti-arrhythmia drug; platelet aggregation inhibitor; sodium channel blocker
streptonigrin [no description available]	2.1	1	pyridines; quinolone	antimicrobial agent; antineoplastic agent
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.11	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
dichlone dichlone: structure	3.21	1
azacitidine Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.	3.21	1	N-glycosyl-1,3,5-triazine; nucleoside analogue	antineoplastic agent
toyocamycin Toyocamycin: 4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry.. toyocamycin : An N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group.	2.1	1	antibiotic antifungal agent; N-glycosylpyrrolopyrimidine; nitrile; ribonucleoside	antimetabolite; antineoplastic agent; apoptosis inducer; bacterial metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	3.21	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
artemisinin (+)-artemisinin : A sesquiterpene lactone obtained from sweet wormwood, Artemisia annua, which is used as an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria.	2	1	organic peroxide; sesquiterpene lactone	antimalarial; plant metabolite
hedamycin [no description available]	2.04	1
frenolicin b frenolicin B: produced by Streptomyces roseofulvus strain AM 3867; structure	1.96	1	benzoisochromanequinone; p-quinones	metabolite
nanaomycin e nanaomycin E: epoxy deriv of nanaomycin A; see also nanaomycin A: 52934-83-5, nanaomycin B: 52934-85-7, nanaomycin C: 58286-55-8; RN in 9th CI for nanaomycin D: 60325-08-8; structure in first source	7.65	3
kalafungin kalafungin: nanaomycin D from Streptomyces rosa & is enantiomer of kalafungin; RN given refers to (3aR-(3aalpha,5alpha,11balpha))-isomer; see also nanaomycin C; structure of kalafungin in first source; structure of nanaomycin in second source	8.47	8
carnosine polaprezinc: stimulates bone growth	2	1	amino acid zwitterion; dipeptide	anticonvulsant; antineoplastic agent; antioxidant; Daphnia magna metabolite; geroprotector; human metabolite; mouse metabolite; neuroprotective agent
actinorhodin actinorhodin: structure. actinorhodin : A member of the class of benzoisochromanequinone that is produced by Streptomyces coelicolor A3(2) and exhibits antibiotic activity.	7.4	2
decitabine [no description available]	3.21	1	2'-deoxyribonucleoside
destomycin a destomycin A: structure given in first source	2.04	1
sesquiterpenes [no description available]	2	1
rg108 RG108: DNA methyltransferase inhibitor; structure in first source	3.93	3	indolyl carboxylic acid
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	4.57	25
genistein [no description available]	3.21	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	1.95	1	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
irumamycin irumamycin: from Streptomyces subflavus; macrolide antibiotic with sugar moiety	2.04	1
monorden monorden: inhibits HSP90 Heat-Shock Proteins, DNA topoisomerase VI and human Topoisomerase II	2	1	cyclic ketone; enone; epoxide; macrolide antibiotic; monochlorobenzenes; phenols	antifungal agent; metabolite; tyrosine kinase inhibitor
am 2604a virustomycin A: from Streptomyces sp. AM-2604	2.04	1
aureothin aureothin: isolated from culture MA-2465; structure. aureothin : A C-nitro compound that is (3Z)-3-[(2E)-2-methyl-3-(4-nitrophenyl)prop-2-en-1-ylidene]tetrahydrofuran which is substituted by a 6-methoxy-3,5-dimethyl-4-oxo-4H-pyran-2-yl group at position 5. It is isolated from the soil bacterium, Streptomyces thioluteus and exhibits antitumor, antifungal, and insecticidal activities.	2.04	1	4-pyranones; C-nitro compound; ketene acetal; olefinic compound; oxolanes	antibacterial agent; antifungal agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; EC 1.6.5.3 [NADH:ubiquinone reductase (H(+)-translocating)] inhibitor
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	1.96	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
echinomycin Echinomycin: A cytotoxic polypeptide quinoxaline antibiotic isolated from Streptomyces echinatus that binds to DNA and inhibits RNA synthesis.	2.04	1	cyclodepsipeptide
hygromycin b [no description available]	2.04	1
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.06	1	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
sgi-1027 SGI-1027: inhibits DNA methyltransferase 1; structure in first source	3.61	2
venturicidin a venturicidin A: structure given in first source	2.04	1

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	3.4	2
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.4	2
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	7.61	2
Malignant Melanoma [description not available]	2.1	1
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	2.1	1
Dermatophytoses [description not available]	1.95	1
Tinea Fungal infection of keratinized tissues such as hair, skin and nails. The main causative fungi include MICROSPORUM; TRICHOPHYTON; and EPIDERMOPHYTON.	1.95	1

nanaomycin a

Description

Cross-References

Synonyms (35)

Research Excerpts

Overview

Treatment

Bioavailability

Roles (1)

Drug Classes (4)

Protein Targets (1)

Inhibition Measurements

Biological Processes (3)

Molecular Functions (7)

Ceullar Components (3)

Bioassays (6)

Research

Studies (27)

Market Indicators

Research Demand Index: 22.07

Study Types