Page last updated: 2024-11-05

6-hydroxyadenosine

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6-Hydroxyadenosine (6-OH-Ado) is a naturally occurring nucleoside analog. It is a potent inhibitor of adenosine deaminase (ADA), an enzyme that catalyzes the deamination of adenosine to inosine. 6-OH-Ado is a potential therapeutic agent for the treatment of ADA deficiency, a genetic disorder that results in the accumulation of deoxyadenosine, which is toxic to cells. 6-OH-Ado has been shown to have antiviral activity against a number of viruses, including HIV-1, hepatitis C virus, and herpes simplex virus. It is also being investigated for its potential use in the treatment of cancer. 6-OH-Ado can be synthesized by a variety of methods, including enzymatic oxidation of adenosine using a flavin-containing monooxygenase. 6-OH-Ado is a promising lead compound for the development of new drugs for the treatment of a variety of diseases.'

Cross-References

ID SourceID
PubMed CID18881
CHEMBL ID236537
SCHEMBL ID3500846
MeSH IDM0054961

Synonyms (33)

Synonym
einecs 222-306-5
brn 0568198
ccris 2559
n(sup 6)-hydroxyadenosine
6-hydroxyamino-9-beta-d-ribofuranosylpurine
6-n-hydroxylaminopurine riboside
n(sup 6)-hydroxylaminopurine riboside
inosine oxime
6-hydroxyaminopurine ribonucleoside
n6-hydroxylaminopurine riboside
adenosine, n-hydroxy-
3414-62-8
n6-hydroxyadenosine
6-n-hydroxyadenosine
6-hydroxyaminopurine riboside
n-hydroxyadenosine
(2r,3r,4s,5r)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
CHEMBL236537
(2r,3r,4s,5r)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
qr2s87k5xc ,
unii-qr2s87k5xc
SCHEMBL3500846
6-hydroxylamino-9-beta-d-ribofuranosylpurine
n6-hydroxyladenosine
inosine, 6-oxime
6-n-hydroxyamino-9-.beta.-d-ribofuranosylpurine
9-.beta.-d-ribofuranosyl-6-(hydroxylamino)purine
6-(hydroxylamino)-9-.beta.-d-ribofuranosylpurine
HY-118793
Q27287458
DTXSID701023373
CS-0068557
AKOS040749992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (30)

Assay IDTitleYearJournalArticle
AID595463Antiproliferative activity against human Caco2 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID300107Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum K12007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID1653809Substrate activity at human mARC2 expressed in Escherichia coli assessed as turnover rates at 1 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by LC-MS analysis based assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID85703In vitro antiviral activity in secondary cultures of rabbit kidney cells infected with HSV type 1 strain HF1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID85569Concentration required to inhibit HSV type 1 strain HF induced cytopathogenic affects by 50%1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID521781Cytotoxicity against human HeLaS3 cells assessed cell viability at 0.05 after 24 hrs by Alamar blue assay2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID300108Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum VS12007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID300104Antimalarial activity against chloroquine, pyrimethamine and cycloguanil-resistant Plasmodium falciparum VS1 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID595459Antiproliferative activity against human HeLa cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID300106Selectivity index, ratio of CC50 for human KB cells to IC50 for Plasmodium falciparum 3D72007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID521783Antiviral activity against Poliovirus G64S infected in HeLaS3 cells at 2 mM after 6 hrs2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID1245165Cytotoxicity against mouse leukemia cells2015Bioorganic & medicinal chemistry, Sep-15, Volume: 23, Issue:18
Imidazopyridines as a source of biological activity and their pharmacological potentials-Infrared and Raman spectroscopic evidence of their content in pharmaceuticals and plant materials.
AID217834Concentration required to inhibit vaccinia virus induced cytopathogenic affects by 50%1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID217966In vitro for antiviral activity in secondary cultures of rabbit kidney cells infected with vaccinia virus1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID96717Compound was tested for its antitumor activity to inhibit 50% of tumor cell growth in mouse leukemia L1210 cell lines.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Purine and 1-deazapurine ribonucleosides and deoxyribonucleosides: synthesis and biological activity.
AID1653794Substrate activity at human mARC1 expressed in Escherichia coli assessed as turnover rates at 1 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by UV-Visible spectroscopy based NADH assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID300103Antimalarial activity against chloroquine,pyrimethamine-resistant Plasmodium falciparum K1 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID228918Molar potency ratio was evaluated1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID521784Metabolic stability in human HeLaS3 cells assessed as JA28-triphosphate at 0.5 mM after 2 hrs by reverse-phase HPLC2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID25507HPLC capacity factor (k')1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID300105Cytotoxicity against human KB cells2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID155036Compound was tested for its antitumor activity to inhibit 50% of tumor cell growth in mouse leukemia P388 cell lines.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Purine and 1-deazapurine ribonucleosides and deoxyribonucleosides: synthesis and biological activity.
AID521785Antiviral activity against Poliovirus infected in compound pre-treated HeLaS3 cells assessed as reduction in viral titer at 0.5 mM after 6 hrs relative to control2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID595460Antiproliferative activity against human K562 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID521786Antiviral activity against Coxsackievirus infected in compound pre-treated HeLaS3 cells assessed as reduction in viral titer at 0.5 mM after 6 hrs relative to control2008Antimicrobial agents and chemotherapy, Mar, Volume: 52, Issue:3
Lethal mutagenesis of picornaviruses with N-6-modified purine nucleoside analogues.
AID300102Antimalarial activity against drug-sensitive Plasmodium falciparum 3D7 after 24 hrs2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Anti-malarial activity of N6-modified purine analogues.
AID595462Antiproliferative activity against human HT-29 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
AID1653804Substrate activity at human mARC1 expressed in Escherichia coli assessed as turnover rates at 1 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by LC-MS analysis based assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID1653799Substrate activity at human mARC2 expressed in Escherichia coli assessed as turnover rates at 1 mM pre-incubated for 3 mins followed by NADH addition and measured after 15 mins by UV-Visible spectroscopy based NADH assay2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Drug Metabolism by the Mitochondrial Amidoxime Reducing Component (mARC): Rapid Assay and Identification of New Substrates.
AID595461Antiproliferative activity against human MCF7 cells after 72 hrs by MTS assay2011European journal of medicinal chemistry, May, Volume: 46, Issue:5
Synthesis and biological activity of novel N6-substituted and 2,N6-disubstituted adenine ribo- and 3'-C-methyl-ribonucleosides as antitumor agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's1 (12.50)18.2507
2000's2 (25.00)29.6817
2010's2 (25.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.50

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.50 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]