Canmetcon
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Identification
YMDB IDYMDB00261
NameGuanosine monophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGuanosine 5'-monophosphate (GMP) is a guanine nucleotide containing one phosphate group esterified to a sugar moiety. It is found in RNA.
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-2.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.05ChemAxon
pKa (Strongest Basic)1.73ChemAxon
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
OdorlessFDB012390
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
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 IDFDB012390
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