CHEBI:75947 - 2'-3'-cGAMP

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ChEBI Name 2'-3'-cGAMP
ChEBI ID CHEBI:75947
Definition A cyclic purine dinucleotide that consists of AMP and GMP units cyclised via 3',5'- and 2',5'-linkages respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anne Morgat
Secondary ChEBI IDs CHEBI:143091
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Formula C20H24N10O13P2
Net Charge 0
Average Mass 674.417
Monoisotopic Mass 674.09995
InChI InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChIKey XRILCFTWUCUKJR-INFSMZHSSA-N
SMILES P1(O[C@@H]2[C@H](O[C@H]([C@@H]2O)N3C=NC=4C(=NC=NC43)N)COP(=O)(O[C@H]5[C@@H](O[C@@H]([C@H]5O)CO1)N6C=NC=7C(NC(=NC76)N)=O)O)(=O)O
ChEBI Ontology
Outgoing 2'-3'-cGAMP (CHEBI:75947) has functional parent Gp[2'-5']Ap[3'] (CHEBI:143097)
2'-3'-cGAMP (CHEBI:75947) is a adenyl ribonucleotide (CHEBI:61296)
2'-3'-cGAMP (CHEBI:75947) is a cyclic purine dinucleotide (CHEBI:47037)
2'-3'-cGAMP (CHEBI:75947) is a guanyl ribonucleotide (CHEBI:61295)
2'-3'-cGAMP (CHEBI:75947) is conjugate acid of 2'-3'-cGAMP(2−) (CHEBI:143093)
Incoming 2'-3'-cGAMP(2−) (CHEBI:143093) is conjugate base of 2'-3'-cGAMP (CHEBI:75947)
IUPAC Name
2-amino-9-[(5R,7R,8R,12aR,14R,15R,15aS,16R)-14-(6-amino-9H-purin-9-yl)-2,10,15,16-tetrahydroxy-2,10-dioxidooctahydro-12H-5,8-methanofuro[3,2-l][1,3,6,9,11,2,10]pentaoxadiphosphacyclotetradecin-7-yl]-1,9-dihydro-6H-purin-6-one
Synonyms Sources
2',5'-3',5'-cGAMP ChEBI
2'-3'-cyclic GMP-AMP SUBMITTER
2'-O,5'-O-[(adenosine-3'-O,5'-O-diyl)bisphosphinico]guanosine ChEBI
c[G(2',5')pA(3',5')p] ChEBI
cyclic (guanosine-(2'→5')-monophosphate-adenosine-(3'→5')-monophosphate) ChEBI
cyclic guanosine monophosphate-adenosine monophosphate ChEBI
Manual Xrefs Databases
1SY PDBeChem
CPD-15224 MetaCyc
Cyclic_guanosine_monophosphate-adenosine_monophosphate Wikipedia
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Registry Number Type Source
1441190-66-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23722158 PubMed citation Europe PMC
23747010 PubMed citation Europe PMC
23910378 PubMed citation Europe PMC
28399655 PubMed citation SUBMITTER
28940468 PubMed citation Europe PMC
30728498 PubMed citation SUBMITTER
Last Modified
18 February 2019