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Identification
YMDB IDYMDB00261
NameGuanosine monophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGuanosine monophosphate, also known as 5'-GMP or guanylic acid, 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.
Structure
Thumb
Synonyms
  • 5'-GMP
  • GMP
  • Guanidine monophosphate
  • Guanosine 5'-monophosphate
  • Guanosine 5'-phosphate
  • Guanosine 5'-phosphorate
  • Guanosine 5'-phosphoric acid
  • guanosine monophosphate
  • guanosine-5'-monophosphate
  • guanosine-5'-phosphate
  • guanosine-phosphate
  • guanylate
  • guanylic acid
  • pG
  • Guanosine-5'-monophosphoric acid
  • Guanosine 5'-monophosphoric acid
  • Guanosine monophosphoric acid
  • e 626
  • 5' Guanylic acid
  • Acid, 5'-guanylic
  • Acid, guanylic
  • Guanosine 5' monophosphate
  • 5'-Monophosphate, guanosine
  • Monophosphate, guanosine
  • 5'-Guanylic acid
CAS number85-32-5
WeightAverage: 363.2206
Monoisotopic: 363.057998961
InChI KeyRQFCJASXJCIDSX-UUOKFMHZSA-N
InChIInChI=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
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 IUPAC Nameguanylate
Chemical FormulaC10H14N5O8P
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=NC2=C1N=C(N([H])[H])N([H])C2=O)C([H])([H])OP(=O)(O[H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water Solubility369 mg/mL [sodium salt, HMP experimental]PhysProp
LogPNot AvailablePhysProp
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • Golgi
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB030896
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
Xanthylic acid + Adenosine triphosphate + L-Glutamine + waterAdenosine monophosphate + Pyrophosphate + L-Glutamic acid + hydron + Guanosine monophosphate
Guanosine monophosphate + Adenosine triphosphateADP + Guanosine diphosphate
KEGG Reactions
water + 3',5'-cyclic GMPGuanosine monophosphate + hydron
Guanosine monophosphate + waterphosphate + Guanosine
Adenosine triphosphate + Xanthylic acid + water + L-GlutamineAdenosine monophosphate + Pyrophosphate + Guanosine monophosphate + L-Glutamic acid + hydron
water + GTPGuanosine monophosphate + phosphate + hydron
Phosphoribosyl pyrophosphate + GuaninePyrophosphate + Guanosine monophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1942000000-27fc2e135f86071ba4d7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1942000000-27fc2e135f86071ba4d7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0941000000-245c5258141d8d2a9fa5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9722000000-9155df338c7516c297b6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9522200000-3e2591b21841c753ec13JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0901000000-fbce35f7dfa73ab5fc11JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-764722cc1b8cc2aaa480JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-c268cdce8dfd6c39fa3cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0409000000-309e438ad8b6162df850JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-0904000000-cf72d0459316801b014eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-abc7bfe7620db1c34775JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-01t9-9113000000-05a8989070e3b89138f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9114000000-9a1071a2e17ea3ca268cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-9113000000-05a8989070e3b89138f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0409000000-309e438ad8b6162df850JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0904000000-cf72d0459316801b014eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-abc7bfe7620db1c34775JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-05cd931f142e4b624c8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-318d089a94a5bcfd20f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-e616291ba80c4abf405cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-7709000000-6c811759b6f078f642a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9800000000-59c4ae8bf5bfa0d23da1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-73f60c52b80206170819JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Gao, X. D., Kaigorodov, V., Jigami, Y. (1999). "YND1, a homologue of GDA1, encodes membrane-bound apyrase required for Golgi N- and O-glycosylation in Saccharomyces cerevisiae." J Biol Chem 274:21450-21456.10409709
Synthesis Reference:Sato, Katsuaki; Matsui, Hiroshi; Ei, Hitoshi; Takinami, Koichi. Guanosine-5'-monophosphate. Jpn. Kokai Tokkyo Koho (1979), 3 pp.
External Links:
ResourceLink
CHEBI ID17345
HMDB IDHMDB01397
Pubchem Compound ID6804
Kegg IDC00144
ChemSpider ID6545
FOODB IDFDB030896
WikipediaGuanosine_monophosphate
BioCyc IDGMP

Enzymes

General function:
Involved in catalytic activity
Specific function:
ATP + xanthosine 5'-phosphate + L-glutamine + H(2)O = AMP + diphosphate + GMP + L-glutamate
Gene Name:
GUA1
Uniprot ID:
P38625
Molecular weight:
58481.80078
Reactions
ATP + xanthosine 5'-phosphate + L-glutamine + H(2)O → AMP + diphosphate + GMP + L-glutamate.
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP2 and PHO5
Gene Name:
NPP1
Uniprot ID:
P25353
Molecular weight:
84733.20313
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of phosphoanhydride bonds of nucleoside tri- and di-phosphates. Has equal high activity toward ADP/ATP, GDP/GTP, and UDP/UTP and approximately 50% less toward CDP/CTP and thiamine pyrophosphate. Has no activity toward GMP. Required for Golgi glycosylation and cell wall integrity. Together with CDC55, required for adenovirus E4orf4 (early region 4 open reading frame 4) induced toxicity, the apyrase activity is not required for this function. Plays a role in sphingolipid synthesis
Gene Name:
YND1
Uniprot ID:
P40009
Molecular weight:
71851.20313
Reactions
ATP + 2 H(2)O → AMP + 2 phosphate.
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and PHO5
Gene Name:
NPP2
Uniprot ID:
P39997
Molecular weight:
57354.10156
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
General function:
Involved in catalytic activity
Specific function:
Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:
PDE2
Uniprot ID:
P06776
Molecular weight:
60999.19922
Reactions
Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.
General function:
Involved in ATP adenylyltransferase activity
Specific function:
Sustains the catabolism of Np-4-N' nucleotides, rather than their synthesis
Gene Name:
APA2
Uniprot ID:
P22108
Molecular weight:
36840.5
Reactions
ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.
General function:
Involved in protein binding
Specific function:
Essential for recycling GMP and indirectly, cGMP
Gene Name:
GUK1
Uniprot ID:
P15454
Molecular weight:
20637.19922
Reactions
ATP + GMP → ADP + GDP.
General function:
Involved in nucleoside metabolic process
Specific function:
IMP + diphosphate = hypoxanthine + 5-phospho- alpha-D-ribose 1-diphosphate
Gene Name:
HPT1
Uniprot ID:
Q04178
Molecular weight:
25190.5
Reactions
IMP + diphosphate → hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.
GMP + diphosphate → guanine + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in hydrolase activity
Specific function:
After transfer of sugars to endogenous macromolecular acceptors, the enzyme converts nucleoside diphosphates to nucleoside monophosphates which in turn exit the Golgi lumen in a coupled antiporter reaction, allowing entry of additional nucleotide sugar from the cytosol
Gene Name:
GDA1
Uniprot ID:
P32621
Molecular weight:
56821.0
Reactions
GDP + H(2)O → GMP + phosphate.

Transporters

General function:
Involved in binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40556
Molecular weight:
41954.0
General function:
Involved in transmembrane transport
Specific function:
Involved in the import of GDP-mannose from the cytoplasm into the Golgi lumen. Defective copy causes severe glycosylation defect and abnormal retention of soluble endoplasmic reticulum proteins. Involved in vanadate sensitivity
Gene Name:
VRG4
Uniprot ID:
P40107
Molecular weight:
37018.30078