Page last updated: 2024-10-15

adenallene

Description

adenallene: structure given in first source; inhibits replication and cytopathic effects of HIV in vitro [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135436544
CHEMBL ID313478
SCHEMBL ID4480283
MeSH IDM0159494

Synonyms (28)

Synonym
CHEMBL313478
mls000757229 ,
n(sup9)-(4-hydroxy-1,2-butadien-1-yl)adenine
nsc-622175
(r)-(-)-9-(4-hydroxy-1,2-butadien-1-yl)adenine
NCI60_006455
r-(-)-adenallene
s-(+)-adenallene
(r)-(-)-n^9-(4-hydroxy-1,2-butadien-1-yl)adenine
(s)-(+)-n^9-(4-hydroxy-1,2-butadien-1-yl)adenine
4-(6-aminopurin-9-yl)buta-2,3-dien-1-ol
114987-18-7
adenallene
nsc622175
2,3-butadien-1-ol, 4-(6-amino-9h-purin-9-yl)-, (+/-)-
smr000529049
4-(6-amino-9h-purin-9-yl)buta-2,3-dien-1-ol
NCGC00246850-01
HMS2885E04
2,3-butadien-1-ol, 4-(6-amino-9h-purin-9-yl)-, (+-)-
9-(4'-hydroxy-1',2'-butadienyl)adenine
SCHEMBL4480283
9-(4-hydroxyl-1,2-butadienyl)adenine
DTXSID20150910
[9-(4-hydroxybut-2-enylidene)purin-9-ium-6-yl]azanide
STARBLD0004547
2,3-butadien-1-ol, 4-(6-amino-9h-purin-9-yl)-
AKOS040745486

Dosage Studied

ExcerptReference
"1-10 microM but the dose-response relationship was poor."( Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.
Maeda, Y; Mitsuya, H; Winter, H; Zemlicka, J, 1996
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency8.91250.140911.194039.8107AID2451
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
TDP1 proteinHomo sapiens (human)Potency3.35120.000811.382244.6684AID686978; AID686979
thioredoxin glutathione reductaseSchistosoma mansoniPotency79.43280.100022.9075100.0000AID485364
P53Homo sapiens (human)Potency35.48130.07319.685831.6228AID504706
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
importin subunit beta-1 isoform 1Homo sapiens (human)Potency4.61095.804836.130665.1308AID540253
snurportin-1Homo sapiens (human)Potency4.61095.804836.130665.1308AID540253
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency4.61095.804816.996225.9290AID540253
lamin isoform A-delta10Homo sapiens (human)Potency5.62340.891312.067628.1838AID1487
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

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

Biological Processes (5)

Processvia Protein(s)Taxonomy
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 (4)

Processvia Protein(s)Taxonomy
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 (3)

Processvia Protein(s)Taxonomy
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 (40)

Assay IDTitleYearJournalArticle
AID213150Inhibition of incorporation of labeled precursor into macromolecules of noninfected SC-1 cells with the compound at a concentration 100 uM determined against thymidine1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID45174Cytotoxic concentration required to inhibit the replication of HIV-1 in CEM-SS human T4 lymphoblastoid cell lines2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.
AID33841Vmax by adenosine deaminase1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
(R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.
AID82111Compound was tested for inhibition of HIV-11992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
(R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.
AID142336Inhibitory activity against murine leukemia L1210 cells1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID32071Compound was evaluated for the inhibition of infectivity and cytopathic effect of HIV-1 in ATH8 cells1996Journal of medicinal chemistry, Aug-16, Volume: 39, Issue:17
Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.
AID213291Inhibition of incorporation of labeled precursor into macromolecules of noninfected SC-1 cells with the compound at a concentration 300 uM determined against thymidine1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID215496Inhibition of incorporation of labeled precursor into macromolecules of noninfected SC-1 cells with the compound at a concentration 100 uM determined against uridine.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID90940Antiviral activity against HCMV was determined; No inhibition1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis of new (+-)-3,5-dihydroxypentyl nucleoside analogues from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation.
AID235487Selectivity index is the ratio of IC50 to EC50 of F-MuLV.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID106900Effective concentration required to inhibit the replication of HIV-1 in MT-2 human T4 lymphoblastoid cell lines2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.
AID45549Effective concentration required to inhibit the replication of HIV-1 in CEMSS human T4 lymphoblastoid cell lines2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.
AID101201Inhibition of incorporation of labeled precursor into macromolecules of noninfected SC-1 cells with the compound at a concentration 300 uM determined against leucine.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID71777Concentration that reduces Friend murine leukemia virus titer by 50%1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID101200Inhibition of incorporation of labeled precursor into macromolecules of noninfected SC-1 cells with the compound at a concentration 100 uM determined against leucine.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID32070Compound was evaluated for the inhibition of replication and cytopathic effect of HIV-1 in ATH8 cells1996Journal of medicinal chemistry, Aug-16, Volume: 39, Issue:17
Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.
AID215497Inhibition of incorporation of labeled precursor into macromolecules of noninfected SC-1 cells with the compound at a concentration 300 uM determined against uridine.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID33819Km by adenosine deaminase1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
(R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination.
AID106885Cytotoxic concentration required to inhibit the replication of HIV-1 in MT-2 human T4 lymphoblastoid cell lines2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.
AID235800Selectivity index which is the ratio of IC50 to EC50 of R-MuLV.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID142441Cytotoxicity was evaluated1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID197658Concentration that reduces Rauscher murine leukemia virus titer by 50%1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID100775Cytotoxicity was evaluated against L1210 leukemia cell line at 1000 ug/disk.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID96631Compound was evaluated for the clonogenic assay with murine leukemia L1210 cells1996Journal of medicinal chemistry, Aug-16, Volume: 39, Issue:17
Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action.
AID105163Effective concentration required to inhibit the replication of HIV-1 in MT-4 human T4 lymphoblastoid cell lines2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.
AID104786Cytotoxic concentration required to inhibit the replication of HIV-1 in MT-4 human T4 lymphoblastoid cell lines2002Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2
Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative.
AID82116Antiviral activity against HIV-1 was determined; No inhibition1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Synthesis of new (+-)-3,5-dihydroxypentyl nucleoside analogues from 1-amino-5-(benzyloxy)pentan-3-ol and their antiviral evaluation.
AID156088Cytotoxicity was evaluated against PO3 cell line at 500 ug/disk.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (14.29)18.7374
1990's6 (42.86)18.2507
2000's2 (14.29)29.6817
2010's3 (21.43)24.3611
2020's1 (7.14)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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]