Record Information
Version1.0
Creation date2015-05-07 20:01:59 UTC
Update date2019-11-26 03:21:53 UTC
Primary IDFDB030764
Secondary Accession Numbers
  • FDB022549
Chemical Information
FooDB Namecyclic-GMP
DescriptionCyclic-gmp, also known as cgmp or guanosine 3',5'-cyclic monophosphate, is a member of the class of compounds known as 3',5'-cyclic purine nucleotides. 3',5'-cyclic purine nucleotides are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Cyclic-gmp is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Cyclic-gmp can be found in a number of food items such as common sage, jew's ear, java plum, and pepper (c. chinense), which makes cyclic-gmp a potential biomarker for the consumption of these food products. Cyclic-gmp can be found primarily in blood and cerebrospinal fluid (CSF), as well as throughout most human tissues. Cyclic-gmp exists in all living species, ranging from bacteria to humans. Moreover, cyclic-gmp is found to be associated with headache.
CAS Number7665-99-8
Structure
Thumb
Synonyms
SynonymSource
CGMPChEBI
Guanosine 3',5'-cyclic monophosphateChEBI
Guanosine 3',5'-cyclic phosphateChEBI
Guanosine cyclic monophosphateChEBI
Guanosine 3',5'-cyclic monophosphoric acidGenerator
Guanosine 3',5'-cyclic phosphoric acidGenerator
Guanosine cyclic monophosphoric acidGenerator
3',5'-Cyclic GMPHMDB
3',5'-GuanosineHMDB
3',5'-Guanosine monophosphateHMDB
Cyclic 3',5'-guanosine monophosphateHMDB
Cyclic guanosine 3',5'-monophosphateHMDB
Cyclic-GMPHMDB
Guanosine 3',5'-cyclic-monophosphateHMDB
Guanosine 3',5'-monophosphateHMDB
Guanosine cyclic-monophosphateHMDB
Guanosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-monophosphate, guanosineHMDB
GMP, CyclicHMDB
Guanosine cyclic-3',5'-monophosphateHMDB
monoPhosphate, guanosine cyclicHMDB
3',5'-monoPhosphate, guanosine cyclicHMDB
Cyclic-3',5'-monophosphate, guanosineHMDB
Guanosine cyclic 3',5'-monophosphateHMDB
Guanosine cyclic 3,5 monophosphateHMDB
Cyclic monophosphate, guanosineHMDB
Guanosine cyclic 3',5' monophosphateHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.79 g/LALOGPS
logP-2ALOGPS
logP-2.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.05ChemAxon
pKa (Strongest Basic)1.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H12N5O7P
IUPAC name9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one
InChI IdentifierInChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
InChI KeyZOOGRGPOEVQQDX-UUOKFMHZSA-N
Isomeric SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
Average Molecular Weight345.2053
Monoisotopic Molecular Weight345.047434275
Classification
Description belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',5'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 3',5'-cyclic purine ribonucleotide
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91adJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2972000000-80320c485cef8d6d91adJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f76-3901000000-c970aad6713a547b2d8fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4590100000-edbc82f84eca5a64f5a5JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uec-2904000000-85af5865e64af24e7691JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0904000000-e34bb3204af3b18ddf11JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-35925bce602ee60e24eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0904000000-93fabfb961527e02671eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0907000000-60b56b2fcc437a04a7b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-16c413e42a41fa5e7262JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udl-3904000000-051a745d5db4f607a935JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0901000000-a2a6721a5a98c3d3e945JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0904000000-fd635f17953dbbff039bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0902000000-36d8b1a240f9f6471886JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-4c75be42ba8dbd671bbfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-06ee1dc93418cde4fe39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-db6612a4a4b92db51507JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-8455683aa1bc0141dd38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-196c267f58b468d3a8f5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-7637808812023bf3fb33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-34c09019debbbd2ef2a6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-db049b28da12291887ceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0904000000-65ab088e129c01a9b140JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-fc45e23a1d622d9a6848JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0900000000-d7d3bc38b1c32086753eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-1709000000-881760c573673e832db8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-f74b8ec55fbea3fdf8cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9600000000-d7f00c8f8cec474c7304JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference