CHEBI:49537 - c-di-GMP

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name c-di-GMP
ChEBI ID CHEBI:49537
Definition A cyclic purine dinucleotide that is the 3',5'-cyclic dimer of MP.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:49535, CHEBI:47036
Supplier Information
Download Molfile XML SDF
Formula C20H24N10O14P2
Net Charge 0
Average Mass 690.41108
Monoisotopic Mass 690.095
InChI InChI=1S/C20H24N10O14P2/c21-19-25-13-7(15(33)27-19)23-3-29(13)17-9(31)11-5(41-17)1-39-45(35,36)44-12-6(2-40-46(37,38)43-11)42-18(10(12)32)30-4-24-8-14(30)26-20(22)28-16(8)34/h3-6,9-12,17-18,31-32H,1-2H2,(H,35,36)(H,37,38)(H3,21,25,27,33)(H3,22,26,28,34)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
InChIKey PKFDLKSEZWEFGL-MHARETSRSA-N
SMILES Nc1nc2n(cnc2c(=O)[nH]1)[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)n1cnc2c1nc(N)[nH]c2=O
Roles Classification
Biological Role(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
signalling molecule
A molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell.
Application(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing c-di-GMP (CHEBI:49537) has role immunomodulator (CHEBI:50846)
c-di-GMP (CHEBI:49537) has role signalling molecule (CHEBI:62488)
c-di-GMP (CHEBI:49537) is a cyclic purine dinucleotide (CHEBI:47037)
c-di-GMP (CHEBI:49537) is a guanyl ribonucleotide (CHEBI:61295)
c-di-GMP (CHEBI:49537) is conjugate acid of c-di-GMP(2−) (CHEBI:58805)
Incoming c-di-GMP(2−) (CHEBI:58805) is conjugate base of c-di-GMP (CHEBI:49537)
IUPAC Name
9,9'-[(2R,3R,3aS,7aR,9R,10R,10aS,14aR)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecine-2,9-diyl]bis(2-amino-1,9-dihydro-6H-purin-6-one)
Synonyms Sources
3',5'-cyclic di-GMP ChEBI
3',5'-Cyclic diguanylic acid KEGG COMPOUND
bis(3',5')-cyclic diguanylic acid ChemIDplus
Bis-(3',5')-cyclic diGMP KEGG COMPOUND
bis-(3'-5')-cyclic dimeric guanosine monophosphate ChEBI
c-(GpGp) ChemIDplus
cdiGMP KEGG COMPOUND
cGpGp ChemIDplus
Cyclic di-3',5'-guanylate KEGG COMPOUND
cyclic di-3',5'-guanylic acid UniProt
cyclic di-GMP ChEBI
cyclic diguanylic acid ChemIDplus
cyclic dinucleotide di-GMP ChEBI
cyclic-bis(3',5')diguanylic acid ChemIDplus
cyclic-bis(3'→5') dimeric GMP IUBMB
guanylyl-(3'→5')-3'-guanylic acid, cyclic 3'→5'''-nucleotide ChemIDplus
Database Links Databases
C-DI-GMP MetaCyc
C16463 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
61093-23-0 CAS Registry Number ChemIDplus
9606190 Reaxys Registry Number Reaxys
9696190 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17646358 PubMed citation Europe PMC
19691499 PubMed citation Europe PMC
20577685 PubMed citation Europe PMC
21320509 PubMed citation Europe PMC
22021215 PubMed citation Europe PMC
22661686 PubMed citation Europe PMC
22728658 PubMed citation Europe PMC
22728659 PubMed citation Europe PMC
22728660 PubMed citation Europe PMC
22821967 PubMed citation Europe PMC
23021863 PubMed citation Europe PMC
23023210 PubMed citation Europe PMC
23202856 PubMed citation Europe PMC
23289502 PubMed citation Europe PMC
23299943 PubMed citation Europe PMC
Last Modified
28 July 2014