cyclic di-3',5'-guanylate (PAMDB110544)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110544
Identification
Name: cyclic di-3',5'-guanylate
Description:Dianion of cyclic di-3',5'-guanylic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • cyclic di-3',5'-GMP
  • c-di-GMP
  • c-di-guanylate
  • cyclic bis(3' -> 5') dimeric GMP
Chemical Formula: C20H22N10O14P2
Average Molecular Weight: 690.0948685518
Monoisotopic Molecular Weight: 690.0948685518
InChI Key: PKFDLKSEZWEFGL-MHARETSRSA-L
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)/p-2/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:C1(C7(C(OP([O-])(=O)OCC4(C(OP([O-])(=O)O1)C(O)C(N3(C2(N=C(N)NC(=O)C=2N=C3)))O4))C(O)C(N6(C5(N=C(N)NC(=O)C=5N=C6)))O7))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as (3'-\u003e5')-cyclic dinucleotides and analogues. These are cyclic compounds consisting of two ribose moieties connected by two 5',3'-phosphodiester bonds to form a cycle. Each ribose unit is N-linked to a nucleic base or an analogue thereof. Some natural (3'-\u003e5')-cyclic dinucleotides include c-di-AMP. Synthetic derivatives are generally more elaborated molecules in which one or the two nucleobase moieties, and/or sugar residues, and/or phosphodiester linkers have been modified.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class (3'-\u003e5')-dinucleotides and analogues
Sub Class(3'-\u003e5')-cyclic dinucleotides and analogues
Direct Parent (3'-\u003e5')-cyclic dinucleotides and analogues
Alternative Parents
Substituents
  • (3'-\u003e5')-cyclic dinucleotide or analogue
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organonitrogen compound
  • Primary amine
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
  • a small molecule (C-DI-GMP)
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight688.4 g/molPubChem
XLogP3-AA-6.9 PubChem
Hydrogen Bond Donor Count6 PubChem
Hydrogen Bond Acceptor Count16 PubChem
Rotatable Bond Count2 PubChem
Exact Mass688.079 g/molPubChem
Monoisotopic Mass688.079 g/molPubChem
Topological Polar Surface Area347 A^2PubChem
Heavy Atom Count46 PubChem
Formal Charge-2 PubChem
Complexity1320 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count8 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
GTP → cyclic di-3',5'-guanylate + diphosphate
cyclic di-3',5'-guanylate + Water → Hydrogen ion + linear dimeric GMP
Pathways:
    Spectra
    Spectra: Not Available
    References
    References: Not Available
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI58805
    KEGGC16463
    PubChem25245336