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CHEBI:71578 - cyclic di-AMP

ChEBI IDCHEBI:71578
ChEBI Namecyclic di-AMP
Stars
DefinitionA cyclic purine dinucleotide that is the 3',5'-cyclic dimer of AMP.
Last Modified21 April 2016
SubmitterSteve
DownloadsMolfile
FormulaC20H24N10O12P2
Net Charge0
Average Mass658.418
Monoisotopic Mass658.10504
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]3[C@@H](O)[C@H](n4cnc5c(N)ncnc54)O[C@@H]3COP(=O)(O)O[C@H]2[C@H]1O
InChIInChI=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
InChIKeyPDXMFTWFFKBFIN-XPWFQUROSA-N
Species of MetaboliteComponentSourceComments
Mycoplasma genitalium (ncbitaxon:2097) - PubMed (22817898)
Roles Classification
Biological Role:
Mycoplasma genitalium metabolite  Any bacterial metabolite produced during a metabolic reaction in Mycoplasma genitalium.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
3',5'-cyclic di-AMPChEBI
bis(3',5')-cyclic diadenylic acidChEBI
bis-(3'-5')-cyclic dimeric adenosine monophosphateChEBI
cyclic di-3',5'-adenylic acidChEBI
Registry NumbersSources
Reaxys:8379358Reaxys
Citations