CHEBI:71578 - cyclic di-AMP

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ChEBI Name cyclic di-AMP
ChEBI ID CHEBI:71578
Definition A cyclic purine dinucleotide that is the 3',5'-cyclic dimer of AMP.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H24N10O12P2
Net Charge 0
Average Mass 658.41190
Monoisotopic Mass 658.10504
InChI InChI=1S/C20H24N10O12P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
InChIKey PDXMFTWFFKBFIN-XPWFQUROSA-N
SMILES Nc1ncnc2n(cnc12)[C@@H]1O[C@@H]2COP(O)(=O)O[C@@H]3[C@@H](COP(O)(=O)O[C@H]2[C@H]1O)O[C@H]([C@@H]3O)n1cnc2c(N)ncnc12
Metabolite of Species Details
Mycoplasma genitalium (NCBI:txid2097) See: PubMed
Roles Classification
Biological Role(s): Mycoplasma genitalium metabolite
Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cyclic di-AMP (CHEBI:71578) has role Mycoplasma genitalium metabolite (CHEBI:131604)
cyclic di-AMP (CHEBI:71578) is a adenyl ribonucleotide (CHEBI:61296)
cyclic di-AMP (CHEBI:71578) is a cyclic purine dinucleotide (CHEBI:47037)
cyclic di-AMP (CHEBI:71578) is conjugate acid of cyclic di-AMP(2−) (CHEBI:71500)
Incoming cyclic di-AMP(2−) (CHEBI:71500) is conjugate base of cyclic di-AMP (CHEBI:71578)
IUPAC Name
(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
Synonyms Sources
3',5'-cyclic di-AMP ChEBI
bis(3',5')-cyclic diadenylic acid ChEBI
bis-(3'-5')-cyclic dimeric adenosine monophosphate ChEBI
cyclic di-3',5'-adenylic acid ChEBI
Registry Number Type Source
8379358 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22211522 PubMed citation Europe PMC
22508860 PubMed citation Europe PMC
23142775 PubMed citation Europe PMC
23192352 PubMed citation Europe PMC
23250743 PubMed citation Europe PMC
Last Modified
21 April 2016