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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:47 UTC
Update Date2021-09-14 15:47:19 UTC
HMDB IDHMDB0060465
Secondary Accession Numbers
  • HMDB60465
Metabolite Identification
Common Namecyclic GMP-AMP
Descriptioncyclic GMP-AMP belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. cyclic GMP-AMP is a very strong basic compound (based on its pKa).
Structure
Data?1563866063
Synonyms
ValueSource
3',5'-Cyclic GMP-AMPChEBI
c[g(3',5')PA(3',5')p]ChEBI
Cyclic guanosine monophosphate-adenosine monophosphateHMDB
Cyclic GMP-AMPChEBI
Chemical FormulaC20H24N10O13P2
Average Molecular Weight674.4113
Monoisotopic Molecular Weight674.099953928
IUPAC Name(1S,6R,8R,9R,10S,15R,17R,18R)-8-(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-17-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione
Traditional Name(1S,6R,8R,9R,10S,15R,17R,18R)-8-(6-aminopurin-9-yl)-3,9,12,18-tetrahydroxy-17-(6-hydroxy-2-imino-3H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ⁵,12λ⁵-diphosphatricyclo[13.3.0.0⁶,¹⁰]octadecane-3,12-dione
CAS Registry NumberNot Available
SMILES
NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N1
InChI Identifier
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-10(31)12-6(40-18)1-38-45(36,37)43-13-7(2-39-44(34,35)42-12)41-19(11(13)32)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
InChI KeyRFCBNSCSPXMEBK-INFSMZHSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Octose monosaccharide
  • Monosaccharide phosphate
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Sugar acid
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.63 g/LALOGPS
logP10(-1.4) g/LALOGPS
logP10(-5.9) g/LChemAxon
logS10(-2.3) g/LALOGPS
pKa (Strongest Acidic)1.53ChemAxon
pKa (Strongest Basic)5.23ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area326.35 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity152.59 m³·mol⁻¹ChemAxon
Polarizability59.04 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cyclic GMP-AMPNC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N15719.0Standard polar33892256
cyclic GMP-AMPNC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N14008.8Standard non polar33892256
cyclic GMP-AMPNC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@@H]5[C@@H](COP(O)(=O)O[C@H]4[C@H]3O)O[C@H]([C@@H]5O)N3C=NC4=C3NC(=N)N=C4O)C2=NC=N16326.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gc0-0319301000-0466348f50e6b25729c42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cyclic GMP-AMP GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Positive-QTOFsplash10-0f79-0900002000-500d12b8f6a2b29fb6752017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Positive-QTOFsplash10-0f79-0900000000-621bf6b5958fba42a56d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Positive-QTOFsplash10-0f79-0900000000-db0aaf099bc43157bfe12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Negative-QTOFsplash10-0fl0-0900006000-8179017d1e14a0ce3aa12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Negative-QTOFsplash10-0f89-0900000000-046bf98314f0af8563652017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Negative-QTOFsplash10-0a59-1900000000-632e05e32dc84b550b912017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Positive-QTOFsplash10-0fb9-0800009000-fc0c083268395937e1222021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Positive-QTOFsplash10-0udi-0900000000-1216c13c790913404c232021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Positive-QTOFsplash10-0udr-0900001000-bd55df92f9536dc822102021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 10V, Negative-QTOFsplash10-00di-0400009000-2b3d59fd6896b5caf8432021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 20V, Negative-QTOFsplash10-0089-0800019000-812b8ac2a8bdc2a6f2112021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cyclic GMP-AMP 40V, Negative-QTOFsplash10-003r-1900212000-5ecec1e36632bfe465952021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11181459
PDB IDNot Available
ChEBI ID71580
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Not Available
Specific function:
Nucleotidyltransferase that catalyzes formation of cyclic GMP-AMP (cGAMP) from ATP and GTP and exhibits antiviral activity. Has antiviral activity by acting as a key cytosolic DNA sensor, the presence of DNA in the cytoplasm being a danger signal that triggers the immune responses. Binds cytosolic DNA directly, leading to activation and synthesis of cGAMP, a second messenger that binds to and activates TMEM173/STING, thereby triggering type-I interferon production.
Gene Name:
MB21D1
Uniprot ID:
Q8N884
Molecular weight:
58813.885
Reactions
Adenosine triphosphate + Guanosine triphosphate → Pyrophosphate + cyclic GMP-AMPdetails