Page last updated: 2024-11-12

cyclic diadenosine phosphate

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Description

cyclic di-AMP : A cyclic purine dinucleotide that is the 3',5'-cyclic dimer of AMP. [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 CID11158091
CHEMBL ID1229884
CHEBI ID71578
SCHEMBL ID18700333
MeSH IDM0521566

Synonyms (37)

Synonym
chebi:71578 ,
CHEMBL1229884 ,
(2r,3r,3as,5r,7ar,9r,10r,10as,12r,14ar)-2,9-bis(6-amino-9h-purin-9-yl)octahydro-2h,7h-difuro[3,2-d:3',2'-j][1,3,7,9,2,8 ]tetraoxadiphosphacyclododecine-3,5,10,12-tetrol 5,12-dioxide
2ba ,
(2r,3r,3as,5r,7ar,9r,10r,10as,12r,14ar)-2,9-bis(6-amino-9h-purin-9-yl)octahydro-2h,7h-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-3,5,10,12-tetrol 5,12-dioxide
C20565
cyclic di-amp
cyclic di-3',5'-adenylic acid
3',5'-cyclic di-amp
(2r,3r,3as,7ar,9r,10r,10as,14ar)-2,9-bis(6-amino-9h-purin-9-yl)octahydro-2h,7h-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-3,5,10,12-tetrol 5,12-dioxide
bis-(3'-5')-cyclic dimeric adenosine monophosphate
bis(3',5')-cyclic diadenylic acid
c-di-amp
HY-12326
CS-3325
54447-84-6
AKOS030526840
SCHEMBL18700333
cyclic diadenylate
3',5'-cyclic diadenylic acid
3'-adenylic acid, adenylyl-(3'->5')-, cyclic nucleotide
cyclic-di-amp
unii-wh9b66eix2
wh9b66eix2 ,
acetic acid, 4-(2,6-dihydro-2,6-dioxo-7-phenylbenzo1,2-b:4,5-bdifuran-3-yl)phenoxy-, 2-ethoxyethyl e
126877-05-2
bis-(3',5')-cyclic-dimeric-adenosine-monophosphate
(2r,3r,3as,5r,7ar,9r,10r,10as,12r,14ar)-2,9-bis(6-amino-9h-purin-9-yl)octahydro-2h,7h-difuro[3,2-d:3',2'-j][1,3,7,9,2,8
]tetraoxadiphosphacyclododecine-3,5,10,12-tetrol 5,12-dioxide
Q27139726
(1s,6r,8r,9r,10s,15r,17r,18r)-8,17-bis(6-aminopurin-9-yl)-3,12-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.3.0.06,10]octadecane-9,18-diol
EX-A3317
c-di-amp(cyclic-di-amp)
bdbm50509429
DTXSID201317771
(2r,3r,3as,7ar,9r,10r,10as,14ar)-2,9-bis(6-amino-9h-purin-9-yl)-3,5,10,12-tetrahydroxyoctahydro-2h,7h-difuro[3,2-d:3',2'-j][1,3,7,9]tetraoxa[2,8]diphosphacyclododecine 5,12-dioxide
(1s,6r,8r,9r,10s,15r,17r,18r)-8,17-bis(6-amino-9h-purin-9-yl)-3,9,12,18-tetrahydroxy-2,4,7,11,13,16-hexaoxa-3,12-diphosphatricyclo[13.3.0.0,octadecane-3,12-dione
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
Mycoplasma genitalium metaboliteAny bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.
[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]

Drug Classes (2)

ClassDescription
cyclic purine dinucleotide
adenyl ribonucleotideA purine riboncleotide where adenine is the purine.
[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 Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Stimulator of interferon genes proteinHomo sapiens (human)EC50 (µMol)3.28730.00581.36117.2000AID1541395; AID1541396; AID1541397; AID1541399; AID1541400; AID1814337; AID1861453
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (24)

Processvia Protein(s)Taxonomy
protein complex oligomerizationStimulator of interferon genes proteinHomo sapiens (human)
autophagosome assemblyStimulator of interferon genes proteinHomo sapiens (human)
activation of innate immune responseStimulator of interferon genes proteinHomo sapiens (human)
pattern recognition receptor signaling pathwayStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of defense response to virus by hostStimulator of interferon genes proteinHomo sapiens (human)
cytoplasmic pattern recognition receptor signaling pathwayStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of macroautophagyStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of protein bindingStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of type I interferon productionStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of interferon-beta productionStimulator of interferon genes proteinHomo sapiens (human)
cellular response to interferon-betaStimulator of interferon genes proteinHomo sapiens (human)
innate immune responseStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIStimulator of interferon genes proteinHomo sapiens (human)
regulation of inflammatory responseStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityStimulator of interferon genes proteinHomo sapiens (human)
protein complex oligomerizationStimulator of interferon genes proteinHomo sapiens (human)
defense response to virusStimulator of interferon genes proteinHomo sapiens (human)
positive regulation of type I interferon-mediated signaling pathwayStimulator of interferon genes proteinHomo sapiens (human)
reticulophagyStimulator of interferon genes proteinHomo sapiens (human)
protein localization to endoplasmic reticulumStimulator of interferon genes proteinHomo sapiens (human)
cellular response to exogenous dsRNAStimulator of interferon genes proteinHomo sapiens (human)
cellular response to organic cyclic compoundStimulator of interferon genes proteinHomo sapiens (human)
antiviral innate immune responseStimulator of interferon genes proteinHomo sapiens (human)
cGAS/STING signaling pathwayStimulator of interferon genes proteinHomo sapiens (human)
proton transmembrane transportStimulator of interferon genes proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
protein bindingStimulator of interferon genes proteinHomo sapiens (human)
proton channel activityStimulator of interferon genes proteinHomo sapiens (human)
protein kinase bindingStimulator of interferon genes proteinHomo sapiens (human)
ubiquitin protein ligase bindingStimulator of interferon genes proteinHomo sapiens (human)
cyclic-di-GMP bindingStimulator of interferon genes proteinHomo sapiens (human)
signaling adaptor activityStimulator of interferon genes proteinHomo sapiens (human)
identical protein bindingStimulator of interferon genes proteinHomo sapiens (human)
protein homodimerization activityStimulator of interferon genes proteinHomo sapiens (human)
2',3'-cyclic GMP-AMP bindingStimulator of interferon genes proteinHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingStimulator of interferon genes proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
Golgi membraneStimulator of interferon genes proteinHomo sapiens (human)
endoplasmic reticulum membraneStimulator of interferon genes proteinHomo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment membraneStimulator of interferon genes proteinHomo sapiens (human)
Golgi membraneStimulator of interferon genes proteinHomo sapiens (human)
autophagosome membraneStimulator of interferon genes proteinHomo sapiens (human)
nucleoplasmStimulator of interferon genes proteinHomo sapiens (human)
mitochondrial outer membraneStimulator of interferon genes proteinHomo sapiens (human)
endosomeStimulator of interferon genes proteinHomo sapiens (human)
autophagosomeStimulator of interferon genes proteinHomo sapiens (human)
peroxisomeStimulator of interferon genes proteinHomo sapiens (human)
endoplasmic reticulum membraneStimulator of interferon genes proteinHomo sapiens (human)
cytosolStimulator of interferon genes proteinHomo sapiens (human)
plasma membraneStimulator of interferon genes proteinHomo sapiens (human)
cytoplasmic vesicle membraneStimulator of interferon genes proteinHomo sapiens (human)
secretory granule membraneStimulator of interferon genes proteinHomo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartment membraneStimulator of interferon genes proteinHomo sapiens (human)
perinuclear region of cytoplasmStimulator of interferon genes proteinHomo sapiens (human)
serine/threonine protein kinase complexStimulator of interferon genes proteinHomo sapiens (human)
STING complexStimulator of interferon genes proteinHomo sapiens (human)
autophagosomeStimulator of interferon genes proteinHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1541398Activation of recombinant human STING haplotype R232H mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541400Activation of recombinant human STING haplotype R293Q mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541397Activation of recombinant human STING haplotype R71H/G230A/R293Q mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541409Activation of recombinant human STING haplotype G230A/R293Q mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay relative to 2'3'cGAMP2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1861453Agonist activity at STING (unknown origin)2022European journal of medicinal chemistry, Aug-05, Volume: 238Discovery of novel Thieno[2,3-d]imidazole derivatives as agonists of human STING for antitumor immunotherapy using systemic administration.
AID1814340Activation of human STING QA mutant expressed in digitonin treated HEK293T cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation by luciferase reporter gene assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
Synthesis and Biological Evaluation of Phosphoester and Phosphorothioate Prodrugs of STING Agonist 3',3'-c-Di(2'F,2'dAMP).
AID1541399Activation of recombinant human STING haplotype G230A/R293Q mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1814338Activation of human STING HAQ mutant expressed in digitonin treated HEK293T cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation by luciferase reporter gene assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
Synthesis and Biological Evaluation of Phosphoester and Phosphorothioate Prodrugs of STING Agonist 3',3'-c-Di(2'F,2'dAMP).
AID1541405Ratio of EC50 for recombinant human wild-type STING expressed in 293T cells in absence of digitonin A to EC50 for recombinant human wild-type STING expressed in 293T cells in presence of digitonin A2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541407Activation of recombinant human STING haplotype R71H/G230A/R293Q mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay relative to 2'3'cGAMP2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541408Activation of recombinant human STING haplotype R232H mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay relative to 2'3'cGAMP2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541395Activation of recombinant human wild-type STING expressed in 293T cells incubated for 7 hrs in absence of digitonin A by bright Glo-luciferase reporter gene assay2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1824688Non-competitive inhibition of pyruvate carboxylase (unknown origin)2022Journal of medicinal chemistry, 01-13, Volume: 65, Issue:1
Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming.
AID1485942Drug metabolism assessed as recombinant Bacillus subtilis YybT-mediated compound hydrolysis by measuring half life at 100 uM by reversed-phase HPLC method2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Synthesis and evaluation of c-di-4'-thioAMP as an artificial ligand for c-di-AMP riboswitch.
AID1814339Activation of human STING REF mutant expressed in digitonin treated HEK293T cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation by luciferase reporter gene assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
Synthesis and Biological Evaluation of Phosphoester and Phosphorothioate Prodrugs of STING Agonist 3',3'-c-Di(2'F,2'dAMP).
AID1575506Binding affinity to anemone STING2019MedChemComm, Dec-01, Volume: 10, Issue:12
Interrupting cyclic dinucleotide-cGAS-STING axis with small molecules.
AID1814337Activation of wild-type human STING expressed in digitonin treated HEK293T cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation by luciferase reporter gene assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
Synthesis and Biological Evaluation of Phosphoester and Phosphorothioate Prodrugs of STING Agonist 3',3'-c-Di(2'F,2'dAMP).
AID1541406Activation of recombinant human wild-type STING expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay relative to 2'3'cGAMP2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1485938Binding affinity to Bacillus substilis 5'-32p-labelled 165 nucleotide RNA assessed as reduction in RNA cleavage measured within 40 hrs by PAGE analysis2017Bioorganic & medicinal chemistry, 07-15, Volume: 25, Issue:14
Synthesis and evaluation of c-di-4'-thioAMP as an artificial ligand for c-di-AMP riboswitch.
AID1541410Activation of recombinant human STING haplotype R293Q mutant expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay relative to 2'3'cGAMP2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541394Binding affinity to recombinant human wild-type STING assessed as change in melting temperature at 150 uM by SYPRO orange dye based differential scanning fluorimetric method2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1541396Activation of recombinant human wild-type STING expressed in 293T cells measured after 30 mins in presence of digitonin A by bright Glo-luciferase reporter gene assay2019Journal of medicinal chemistry, 12-12, Volume: 62, Issue:23
Enzymatic Preparation of 2'-5',3'-5'-Cyclic Dinucleotides, Their Binding Properties to Stimulator of Interferon Genes Adaptor Protein, and Structure/Activity Correlations.
AID1814341Activation of human STING Q mutant expressed in digitonin treated HEK293T cells co-expressing IRF3-activated ISRE assessed as IRF3 reporter activation by luciferase reporter gene assay2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
Synthesis and Biological Evaluation of Phosphoester and Phosphorothioate Prodrugs of STING Agonist 3',3'-c-Di(2'F,2'dAMP).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (50.00)24.3611
2020's3 (50.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.85

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 Index12.85 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]