Record Information
Version1.0
Creation date2015-05-07 20:27:25 UTC
Update date2020-09-17 15:38:55 UTC
Primary IDFDB030896
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGMP
DescriptionGuanosine monophosphate, also known as guanylic acid or 5'-GMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Guanosine monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Guanosine monophosphate exists in all living species, ranging from bacteria to humans. Within humans, guanosine monophosphate participates in a number of enzymatic reactions. In particular, guanosine triphosphate and guanosine monophosphate can be biosynthesized from diguanosine tetraphosphate; which is catalyzed by the enzyme bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]. In addition, guanosine monophosphate can be biosynthesized from guanosine diphosphate; which is mediated by the enzyme ectonucleoside triphosphate diphosphohydrolase 5. In humans, guanosine monophosphate is involved in purine metabolism. A purine ribonucleoside 5'-monophosphate having guanine as the nucleobase. Outside of the human body, Guanosine monophosphate has been detected, but not quantified in, several different foods, such as rosemaries, common chokecherries, pigeon pea, rices, and horseradish tree. This could make guanosine monophosphate a potential biomarker for the consumption of these foods.
CAS Number85-32-5
Structure
Thumb
Synonyms
SynonymSource
5'-GMPChEBI
GMPChEBI
Guanosine 5'-phosphateChEBI
Guanosine-5'-monophosphateChEBI
Guanylic acidChEBI
pGChEBI
Guanosine 5'-monophosphateKegg
Guanosine 5'-phosphoric acidGenerator
Guanosine-5'-monophosphoric acidGenerator
GuanylateGenerator
Guanosine 5'-monophosphoric acidGenerator
Guanosine monophosphoric acidGenerator
e 626HMDB
Guanidine monophosphateHMDB
Guanosine 5'-phosphorateHMDB
Guanosine-5'-phosphateHMDB
Guanosine-phosphateHMDB
5' Guanylic acidHMDB
Acid, 5'-guanylicHMDB
Acid, guanylicHMDB
Guanosine 5' monophosphateHMDB
5'-monoPhosphate, guanosineHMDB
monoPhosphate, guanosineHMDB
5'-Guanylic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.56 g/LALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.29ChemAxon
pKa (Strongest Basic)0.38ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.75 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.49 m³·mol⁻¹ChemAxon
Polarizability30.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14N5O8P
IUPAC name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
InChI KeyRQFCJASXJCIDSX-UUOKFMHZSA-N
Isomeric SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
Average Molecular Weight363.2206
Monoisotopic Molecular Weight363.057998961
Classification
Description Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGMP, 6 TMS, GC-MS Spectrumsplash10-014i-1942000000-27fc2e135f86071ba4d7Spectrum
GC-MSGMP, non-derivatized, GC-MS Spectrumsplash10-014i-1942000000-27fc2e135f86071ba4d7Spectrum
GC-MSGMP, non-derivatized, GC-MS Spectrumsplash10-014i-0941000000-245c5258141d8d2a9fa5Spectrum
Predicted GC-MSGMP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9722000000-9155df338c7516c297b6Spectrum
Predicted GC-MSGMP, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9522200000-3e2591b21841c753ec13Spectrum
Predicted GC-MSGMP, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9113000000-05a8989070e3b89138f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9113000000-05a8989070e3b89138f1Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c340c748805ec82deb0dSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-3009000000-5d594db970a4fea1099eSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9011000000-8335076473133728e58fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0901000000-fbce35f7dfa73ab5fc11Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-764722cc1b8cc2aaa480Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-c268cdce8dfd6c39fa3cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0409000000-309e438ad8b6162df850Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-0904000000-cf72d0459316801b014eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-abc7bfe7620db1c34775Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0409000000-309e438ad8b6162df850Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0904000000-cf72d0459316801b014eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-abc7bfe7620db1c34775Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0904000000-cf72d0459316801b014eSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1f479e6ff94baf0265bcSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-1dd27aac9ee9a0882191Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-2a576138a3c13311d4a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-7709000000-6c811759b6f078f642a2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9800000000-59c4ae8bf5bfa0d23da1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-73f60c52b80206170819Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3009000000-dfcdbb4161e7f5a72765Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9101000000-17630021dd251e559ca9Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
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