Page last updated: 2024-09-23

2'3'-didehydro-2'3'-dideoxyadenosine

Description

2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64975
CHEMBL ID290427
SCHEMBL ID112551
MeSH IDM0204360

Synonyms (29)

Synonym
2',3'-dideoxy-2'3'-didehydroadenosine
7057-48-9
adenosine, 2',3'-didehydro-2',3'-dideoxy-
[(2s,5r)-5-(6-aminopurin-9-yl)-2,5-dihydrofuran-2-yl]methanol
ddeado
2',3'-didehydro-2',3'-dideoxyadenosine
2',3'-dideoxy-2'-adenosinene
CHEMBL290427
AKOS004900469
beta-l-d4a
nsc 108602
unii-sk35877hi5
sk35877hi5 ,
2'3'-ddda
2'3'-didehydro-2'3'-dideoxyadenosine
2',3'-dideoxy-2',3'-didehydroadenosine
didanosine impurity i [ep impurity]
didanosine impurity i
didanosine impurity i [who-ip]
SCHEMBL112551
JFUOUIPRAAGUGF-NKWVEPMBSA-N
[(2s,5r)-5-(6-amino-9h-purin-9-yl)-2,5-dihydrofuran-2-yl]methanol
((2s,5r)-5-(6-amino-9h-purin-9-yl)-2,5-dihydrofuran-2-yl)methanol
CS-0018411
HY-100260
DTXSID70875924
AS-34578
Q27289250
A866596

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Deoxycytidine kinaseHomo sapiens (human)Km620.00000.40003.57908.5000AID55392
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
pyrimidine nucleotide metabolic processDeoxycytidine kinaseHomo sapiens (human)
CMP biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
dAMP salvageDeoxycytidine kinaseHomo sapiens (human)
nucleoside phosphate biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
adenosine catabolic processAdenosine deaminase Bos taurus (cattle)
cell adhesionAdenosine deaminase Bos taurus (cattle)
nucleotide metabolic processAdenosine deaminase Bos taurus (cattle)
purine ribonucleoside monophosphate biosynthetic processAdenosine deaminase Bos taurus (cattle)
inosine biosynthetic processAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
deoxyadenosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxycytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxyguanosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
ATP bindingDeoxycytidine kinaseHomo sapiens (human)
protein homodimerization activityDeoxycytidine kinaseHomo sapiens (human)
cytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
adenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
protein bindingAdenosine deaminase Bos taurus (cattle)
zinc ion bindingAdenosine deaminase Bos taurus (cattle)
2'-deoxyadenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleoplasmDeoxycytidine kinaseHomo sapiens (human)
cytosolDeoxycytidine kinaseHomo sapiens (human)
mitochondrionDeoxycytidine kinaseHomo sapiens (human)
cytoplasmDeoxycytidine kinaseHomo sapiens (human)
lysosomeAdenosine deaminase Bos taurus (cattle)
cytoplasmic vesicle lumenAdenosine deaminase Bos taurus (cattle)
anchoring junctionAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (47)

Assay IDTitleYearJournalArticle
AID23359Hydrolysis half life in glycine/HCl buffer at the specified pH of 1.51999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID105753Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID25128Half life of the compound1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID33983Inhibitory activity against bovine liver adenosine Kinase; NS, NI/Ino=nonsubstrate, noninhibitor/inhibitor1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID47113In vitro inhibition of HIV-2 replication in human T-lymphocytic cells (CEM).1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID229420Selectivity ratio CD50 to ED501987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
AID1068979Antiviral activity against HIV-2 ROD infected in human MT4 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID33650Kcat/KM of compound against adenosine deaminase (ADA) was determined; Not available2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID46975In vitro cytotoxic concentration in CEM cells.1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID1068976Cytotoxicity against human CEM/0 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID235291Compound was evaluated for its ability to inhibit the growth of HIV-2 in CEM cell culture (CC50/EC50)1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID19628Partition coefficient (logP)1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID32065Protection of ATH8 cells against the cytopathic effect of HIV.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105750Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID43987Effect of compound against Moloney murine sarcoma virus (MSV)-induced transformation of C3H/3T3 embryo murine fibroblasts1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID1068975Antiviral activity against HIV-2 ROD infected in thymidine kinase-deficient human CEM cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID105521Anti-HIV activity was determined as dose required to protect 50% of the HIV-infected MT-4 cells against destruction1987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
AID33647Kcat value against adenosine deaminase (ADA); Not available2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID47111In vitro inhibition of HIV-1 replication in human T-lymphocytic cells (CEM).1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID1068978Cytotoxicity against human MT4 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID33645Menten constant against adenosine deaminase (ADA)2004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID104946Cytotoxicity was determined as the dose required to reduce the viability of uninfected MT-4 cells by 50%1987Journal of medicinal chemistry, Nov, Volume: 30, Issue:11
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.
AID26764Compound was evaluated for its lipophilicity by 1-octanol/water (phosphate buffer, pH 7.0) and the partition coefficient (log P) was reported.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID55392Inhibitory activity against human deoxycytidine kinase1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID46966Compound was evaluated for its concentration (potency) to inhibit the growth of CEM cells.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID44134Minimal cytotoxic concentration required to cause morphological alteration of C3H/3T3 fibroblast culture cells1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID23365Hydrolysis half life in phosphate buffer at the specified pH of 7.3; Not available1999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID11772Compound was evaluated for esterase half-life (t 1/2) period using Pig Liver Esterase (PLE) assay; ND is not determined1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID234204Therapeutic index (Ratio = ID50/ED50).1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID1068977Antiviral activity against HIV-2 ROD infected in human CEM/0 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID8121Ability to get deaminated by adenosine deaminase (ADA); Expressed as t1/22004Journal of medicinal chemistry, Jun-17, Volume: 47, Issue:13
Synthesis, structure-activity relationships, and drug resistance of beta-d-3'-fluoro-2',3'-unsaturated nucleosides as anti-HIV Agents.
AID47128Compound was evaluated for its effective concentration (potency) to inhibit the growth of HIV-1 in CEM cell culture.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID1068980Antiviral activity against HIV-1 3B infected in human MT4 cells2014Bioorganic & medicinal chemistry letters, Feb-01, Volume: 24, Issue:3
Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents.
AID235290Compound was evaluated for its ability to inhibit the growth of HIV-1 in CEM cell culture (CC50/EC50)1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID105764Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105762Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID47129Compound was evaluated for its effective concentration (potency) to inhibit the growth of HIV-2 in CEM cell culture.1999Bioorganic & medicinal chemistry letters, Sep-06, Volume: 9, Issue:17
Simple mono-derivatisation of the aryl moiety of D4A and DDA-based phosphoramidate prodrugs significantly enhances their anti-HIV potency in cell culture.
AID105759Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.00032 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID33640Inhibitory activity against bovine adenosine deaminase; very weak substrate or inhibitor1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID105756Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105760Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.008 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID28386Partition coefficient in 1-octanol and 10 mM aqueous potassium phosphate buffer at pH 7.41989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3'-azido-2',3'-dideoxy-2,6-diaminopurine ribosides.
AID235638Selectivity index by CC50 of CEM cells/EC50 of CEM cells against HIV-11999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
AID105766Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID164942Inhibitory activity against purine nucleoside phosphorylases from human blood and calf spleen; NS, NI/Ino=nonsubstrate, noninhibitor/inhibitor1997Journal of medicinal chemistry, Nov-21, Volume: 40, Issue:24
Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine.
AID32066Required dose to reduce viability of normal uninfected ATH8 cells.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID23360Hydrolysis half life in glycine/HCl buffer at the specified pH of 3.01999Journal of medicinal chemistry, May-06, Volume: 42, Issue:9
cycloSal-Pronucleotides of 2',3'-dideoxyadenosine and 2', 3'-dideoxy-2',3'-didehydroadenosine: synthesis and antiviral evaluation of a highly efficient nucleotide delivery system.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (15.00)18.7374
1990's5 (25.00)18.2507
2000's10 (50.00)29.6817
2010's2 (10.00)24.3611
2020's0 (0.00)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%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]