Record Information
Version1.0
Creation Date2016-09-30 22:45:22 UTC
Update Date2020-06-04 20:47:13 UTC
BMDB IDBMDB0001397
Secondary Accession Numbers
  • BMDB01397
Metabolite Identification
Common NameGuanosine monophosphate
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 possibly soluble (in water) and a moderately basic compound (based on its pKa). Guanosine monophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC10H14N5O8P
Average Molecular Weight363.2206
Monoisotopic Molecular Weight363.057998961
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
Traditional Nameguanylate
CAS Registry Number85-32-5
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Golgi
  • Lysosome
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility369 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1942000000-27fc2e135f86071ba4d7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1942000000-27fc2e135f86071ba4d7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0941000000-245c5258141d8d2a9fa5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9722000000-9155df338c7516c297b6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9522200000-3e2591b21841c753ec13View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0901000000-fbce35f7dfa73ab5fc11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-764722cc1b8cc2aaa480View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-c268cdce8dfd6c39fa3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0409000000-309e438ad8b6162df850View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-0904000000-cf72d0459316801b014eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-abc7bfe7620db1c34775View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9113000000-05a8989070e3b89138f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9113000000-05a8989070e3b89138f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0409000000-309e438ad8b6162df850View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0904000000-cf72d0459316801b014eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-abc7bfe7620db1c34775View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c340c748805ec82deb0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-3009000000-5d594db970a4fea1099eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-9011000000-8335076473133728e58fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0904000000-cf72d0459316801b014eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1f479e6ff94baf0265bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-1dd27aac9ee9a0882191View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-05cd931f142e4b624c8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-318d089a94a5bcfd20f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-e616291ba80c4abf405cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-7709000000-6c811759b6f078f642a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9800000000-59c4ae8bf5bfa0d23da1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-73f60c52b80206170819View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Golgi
  • Lysosome
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • Bladder
  • Epidermis
  • Heart
  • Intestine
  • Milk
  • Neuron
  • Platelet
  • Smooth Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
HeartExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified1.8 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified8.3 uMNot SpecifiedNot SpecifiedNormal details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Smooth MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001397
DrugBank IDDB01972
Phenol Explorer Compound IDNot Available
FooDB IDFDB030896
KNApSAcK IDC00019635
Chemspider ID6545
KEGG Compound IDC00144
BioCyc IDGMP
BiGG ID34024
Wikipedia LinkGuanosine_monophosphate
METLIN ID6216
PubChem Compound6804
PDB IDNot Available
ChEBI ID17345
References
Synthesis ReferenceSato, Katsuaki; Matsui, Hiroshi; Ei, Hitoshi; Takinami, Koichi. Guanosine-5'-monophosphate. Jpn. Kokai Tokkyo Koho (1979), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]
  2. Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44. [PubMed:7196410 ]

Enzymes

General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
Q56JW4
Molecular weight:
19537.0
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
O46411
Molecular weight:
64841.0
Reactions
Guanosine monophosphate + Water → Guanosine + Hydrogen phosphatedetails
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
As cone-specific cGMP phosphodiesterase, it plays an essential role in light detection and cone phototransduction by rapidly decreasing intracellular levels of cGMP.
Gene Name:
PDE6C
Uniprot ID:
P16586
Molecular weight:
98798.0
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
This protein participates in processes of transmission and amplification of the visual signal.
Gene Name:
PDE6A
Uniprot ID:
P11541
Molecular weight:
99341.0
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
This protein participates in processes of transmission and amplification of the visual signal. Necessary for the formation of a functional phosphodiesterase holoenzyme.
Gene Name:
PDE6B
Uniprot ID:
P23439
Molecular weight:
98331.0
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining the intracellular balance of A and G nucleotides (Probable). Plays a role in modulating cellular differentiation (By similarity).
Gene Name:
GMPR2
Uniprot ID:
Q32L93
Molecular weight:
38033.0
Reactions
Inosinic acid + Ammonia + NADP → Guanosine monophosphate + NADPHdetails
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase a
Specific function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6H
Uniprot ID:
P22571
Molecular weight:
9102.0
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:8530505). Specifically regulates nitric-oxide-generated cGMP (By similarity).
Gene Name:
PDE5A
Uniprot ID:
Q28156
Molecular weight:
98627.0
Reactions
Guanosine 2',3'-cyclic phosphate + Water → Guanosine monophosphatedetails
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase a
Specific function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6G
Uniprot ID:
P04972
Molecular weight:
9669.0
General function:
Signal transduction mechanisms
Specific function:
Receptor for the C-type natriuretic peptide NPPC/CNP hormone. Has guanylate cyclase activity upon binding of its ligand. May play a role in the regulation of skeletal growth.
Gene Name:
NPR2
Uniprot ID:
P46197
Molecular weight:
117146.0
General function:
Nucleotide transport and metabolism
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway (By similarity).
Gene Name:
HPRT1
Uniprot ID:
Q3SZ18
Molecular weight:
24498.0
Reactions
Guanosine monophosphate + Pyrophosphate → Guanine + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q2KIC5
Molecular weight:
23061.0
Reactions
Guanosine triphosphate + Water → Guanosine monophosphate + Pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the phosphorylation of GMP to GDP. Essential enzyme for recycling GMP and indirectly, cyclic GMP (cGMP) (PubMed:8243671, PubMed:29515371, PubMed:7911663). Involved in the cGMP metabolism in photoreceptors (PubMed:29515371, PubMed:8243671).
Gene Name:
GUK1
Uniprot ID:
P46195
Molecular weight:
21910.0
Reactions
Adenosine triphosphate + Guanosine monophosphate → ADP + Guanosine diphosphatedetails
General function:
Involved in GTP binding
Specific function:
Not Available
Gene Name:
GBP6
Uniprot ID:
Q0V7P3
Molecular weight:
23827.0
General function:
Involved in GTP binding
Specific function:
Not Available
Gene Name:
GBP1
Uniprot ID:
A5D955
Molecular weight:
25588.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
GMPS
Uniprot ID:
Q2T9U0
Molecular weight:
77865.0
Reactions
Adenosine triphosphate + Xanthylic acid + Water + L-Glutamine → Adenosine monophosphate + Pyrophosphate + L-Glutamic acid + Guanosine monophosphatedetails
Adenosine triphosphate + Xanthylic acid + Ammonia → Adenosine monophosphate + Pyrophosphate + Guanosine monophosphatedetails
General function:
Not Available
Specific function:
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:
NUDT2
Uniprot ID:
Q29RJ1
Molecular weight:
16775.0
Reactions
Diguanosine tetraphosphate + Water → Guanosine triphosphate + Guanosine monophosphatedetails
General function:
Not Available
Specific function:
Uridine diphosphatase (UDPase) that promotes protein N-glycosylation and ATP level regulation. UDP hydrolysis promotes protein N-glycosylation and folding in the endoplasmic reticulum, as well as elevated ATP consumption in the cytosol via an ATP hydrolysis cycle. Together with CMPK1 and AK1, constitutes an ATP hydrolysis cycle that converts ATP to AMP and results in a compensatory increase in aerobic glycolysis. The nucleotide hydrolyzing preference is GDP > IDP > UDP, but not any other nucleoside di-, mono- or triphosphates, nor thiamine pyrophosphate. Plays a key role in the AKT1-PTEN signaling pathway by promoting glycolysis in proliferating cells in response to phosphoinositide 3-kinase (PI3K) signaling (By similarity).
Gene Name:
ENTPD5
Uniprot ID:
E1BPW0
Molecular weight:
47888.0
Reactions
Guanosine diphosphate + Water → Guanosine monophosphate + Hydrogen phosphatedetails